13-hydroxy-12,14-dioxa-13λ5-phosphapentacyclo[13.8.0.02,11.03,8.018,23]tricosa-1(15),2,4,6,8,10,16,18,20,22-decaen-13-one

• ChemBase编号: 79706
• 分子式: C20H13O4P
• 平均质量: 348.288581
• 单一同位素质量: 348.05514553
• SMILES: P1(=O)(Oc2c(c3ccccc3cc2)c2c3ccccc3ccc2O1)O
• Canonical SMILES: OP1(=O)Oc2ccc3c(c2c2c(O1)ccc1c2cccc1)cccc3
• InChI: InChI=1S/C20H13O4P/c21-25(22)23-17-11-9-13-5-1-3-7-15(13)19(17)20-16-8-4-2-6-14(16)10-12-18(20)24-25/h1-12H,(H,21,22)
• InChIKey: JEHUZVBIUCAMRZ-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 13-hydroxy-12,14-dioxa-13λ^5-phosphapentacyclo[13.8.0.0^2,^1^1.0^3,^8.0^1^8,^2^3]tricosa-1(15),2,4,6,8,10,16,18,20,22-decaen-13-one; 13-hydroxy-12,14-dioxa-13λ^5-phosphapentacyclo[13.8.0.0^2,^1^1.0^3,^8.0^1^8,^2^3]tricosa-1(23),2,4,6,8,10,15,17,19,21-decaen-13-one; 13-hydroxy-12,14-dioxa-13$l^{5}-phosphapentacyclo[13.8.0.0^{2,11}.0^{3,8}.0^{18,23}]tricosa-1(15),2,4,6,8,10,16,18,20,22-decaen-13-one; 13-hydroxy-12,14-dioxa-13λ^5-phosphapentacyclo[13.8.0.0^2,11.0^3,8.0^18,23]tricosa-1(23),2,4,6,8,10,15,17,19,21-decaen-13-one; 13-hydroxy-12,14-dioxa-13λ^5-phosphapentacyclo[13.8.0.0^2,^1^1.0^3,^8.0^1^8,^2^3]tricosa-1(15),2(11),3,5,7,9,16,18,20,22-decaen-13-one; 13-hydroxy-12,14-dioxa-13$l^{5}-phosphapentacyclo[13.8.0.0^{2,11}.0^{3,8}.0^{18,23}]tricosa-1(23),2,4,6,8,10,15,17,19,21-decaen-13-one
• IUPAC传统名: 13-hydroxy-12,14-dioxa-13λ^5-phosphapentacyclo[13.8.0.0^2,^1^1.0^3,^8.0^1^8,^2^3]tricosa-1(15),2,4,6,8,10,16,18,20,22-decaen-13-one; 13-hydroxy-12,14-dioxa-13λ^5-phosphapentacyclo[13.8.0.0^2,^1^1.0^3,^8.0^1^8,^2^3]tricosa-1(23),2,4,6,8,10,15,17,19,21-decaen-13-one; 13-hydroxy-12,14-dioxa-13$l^{5}-phosphapentacyclo[13.8.0.0^{2,11}.0^{3,8}.0^{18,23}]tricosa-1(15),2,4,6,8,10,16,18,20,22-decaen-13-one; 13-hydroxy-12,14-dioxa-13λ^5-phosphapentacyclo[13.8.0.0^2,11.0^3,8.0^18,23]tricosa-1(23),2,4,6,8,10,15,17,19,21-decaen-13-one; 13-hydroxy-12,14-dioxa-13λ^5-phosphapentacyclo[13.8.0.0^2,^1^1.0^3,^8.0^1^8,^2^3]tricosa-1(15),2(11),3,5,7,9,16,18,20,22-decaen-13-one; 13-hydroxy-12,14-dioxa-13$l^{5}-phosphapentacyclo[13.8.0.0^{2,11}.0^{3,8}.0^{18,23}]tricosa-1(23),2,4,6,8,10,15,17,19,21-decaen-13-one
• 别名: 联萘酚磷酸酯; (S)-4-羟基二萘并[2,1-d:1′,2′-f][1,3,2]二噁磷杂庚英-4-氧化物; (S)-(+)-1,1′-联萘-2,2′-二基磷酸氢酯; S-联萘酚磷酸酯; (R)-4-羟基二萘并[2,1-d:1′,2′-f][1,3,2]二噁磷杂庚英-4-氧化物; (R)-(-)-1,1′-联萘-2,2′-二基磷酸氢酯; R-联萘酚磷酸酯; (S)-(+)-1,1'-二萘基-2,2'基 双磷酸氢酯; (R)-(-)-1,1'-二萘基-2,2'基 氧-磷酸; (11bS)-4-Hydroxydinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepin 4-Oxide; (+)-1,1'-Binaphthyl-2,2'-diyl Hydrogen Phosphate; (S)-1,1'-Binaphthyl-2,2'-diyl Hydrogen Phosphate; (S)-(+)-BNDHP; (S)-(+)-1,1'-Binaphthyl-2,2'-diyl Hydrogen Phosphate; (11bR)-4-Hydroxydinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepin 4-Oxide; (-)-1,1'-Binaphthyl-2,2'-diyl Hydrogen Phosphate; (R)-1,1'-Binaphthyl-2,2'-diyl Hydrogen Phosphate; (R)-BNPPA(R)-(-)-BNDHP; (R)-(-)-1,1'-Binaphthyl-2,2'-diyl Hydrogen Phosphate; R-(-)-1,1'-Binaphthyl-2,2'-diyl hydrogenphosphate; 1,1'-Binaphthyl-2,2'-diyl hydrogen phosphate; 2-hydroxy-2lambda~5~-dinaphtho[2,1-d:1,2-f][1,3,2]dioxaphosphepin-2-one; (R)-(-)-1,1'-Binaphthyl-2,2'-diylhydrogenphosphate; BNDHP; 1,1′-Binaphthyl-2,2′-diyl hydrogenphosphate; (S)-(+)-1,1′-Binaphthalene-2,2′-diyl hydrogen phosphate; (S)-4-Hydroxydinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepin-4-oxide; (S)-(+)-1,1′-Binaphthyl-2,2′-diyl hydrogenphosphate; (R)-(-)-1,1′-Binaphthalene-2,2′-diyl hydrogen phosphate; (R)-4-Hydroxydinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepin-4-oxide; (R)-(-)-1,1′-Binaphthyl-2,2′-diyl hydrogenphosphate; (S)-(+)-1,1′-Binaphthalene-2,2′-diyl hydrogen phosphate; (R)-(-)-1,1′-Binaphthalene-2,2′-diyl hydrogen phosphate; R(-)-1,1'-BINAPHTHYL-2,2'-DIYL HYDROGEN PHOSPHATE; (S)-(+)-1,1'-Binaphthalene-2,2'-diyl hydrogen phosphate; (S)-(+)-BNP acid; (S)-(+)-1,1'-Binaphthyl-2,2'-diyl hydrogen phosphate; (R)-(-)-1,1'-Binaphthalene-2,2'-diyl hydrogen phosphate; (R)-(-)-BNP acid; (R)-(-)-1,1'-Binaphthyl-2,2'-diyl hydrogen phosphate

登记号

• CAS号: 39648-67-4; 35193-63-6; 35193-64-7
• EC号: 252-425-8
• MDL号: MFCD00010045
• Beilstein号: 4787775; 4713363
• PubChem SID: 24857622; 162044469; 24848607; 24854961; 24854963; 24848611
• PubChem CID: 99589

理论计算性质

• Acid pKa: 0.8249028
• 质子受体: 2
• 质子供体: 1
• LogD (pH = 5.5): 2.3304372
• LogD (pH = 7.4): 2.3282962
• Log P: 4.7046676
• 摩尔折射率: 95.1503 cm^3
• 极化性: 40.68298 Å^3
• 极化表面积: 55.76 Å^2
• 可自由旋转的化学键: 0
• 里宾斯基五规则: true

分子性质

理化性质

• 溶解度: DMSO; Methanol (hot)
• 外观: Off-White Solid
• 熔点: >300°C; ≥300 °C
• 比旋光度: [α]20/D +600±15°, c = 1% in methanol; [α]20/D -600±15°, c = 1% in methanol; [α]20/D -605°, c = 1.35 in methanol; [α]22/D +595°, c = 1.35 in methanol; +605 (c=1 in methanol); -605 (c=1 in methanol)

安全信息

• 保存条件: Refrigerator
• 欧盟危险性物质标志: 刺激性(Irritant) (Xi)
• 德国WGK号: 3
• 危险公开号: 36/37/38
• 安全公开号: 26-36; 26-37
• TSCA收录: 否
• GHS危险品标识: GHS07
• GHS警示词: Warning
• GHS危险声明: H315-H319-H335
• GHS警示性声明: P261-P305 + P351 + P338; P261-P305+P351+P338-P302+P352-P321-P405-P501A
• 个人保护装置: dust mask type N95 (US), Eyeshields, Gloves; Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

产品相关信息

• 纯度: >99%; ≥98%; ≥98.0% (T); 90%; 95%; 97%; 98+%; 99%
• 级别: purum
• Empirical Formula (Hill Notation): C20H13O4P

详细说明

MP Biomedicals - 02199549

White powder.
Optical Purity: >99%
Chemical Purity: >98%

Sigma Aldrich - 248932

包装
1, 5 g in glass bottle
Application
用于手性布朗斯特酸催化的不对称 Mannich 反应。
用于氢羧基化反应的手性配体。1与铑络合并调节重氮化合物的不对称偶极环加成反应。2许多已证明难以分离的外消旋胺可以使用该手性酸进行分离。3钯衍生物已用于不对称氢羧基化反应，4并且铑衍生物已用于偶极环加成反应。5
Protocols & Applications
Reductive Amination using BINOL-Derived Chiral Phosphoric Acids

Sigma Aldrich - 248940

Application
用作不对称 Mannich 反应中手性布朗斯特酸催化剂。1
包装
1, 5 g in glass bottle
Protocols & Applications
Reductive Amination using BINOL-Derived Chiral Phosphoric Acids

Sigma Aldrich - 14380

Other Notes
该手性阻旋异构环磷酸与各种有机碱形成良好的结晶盐。使用该酸易于溶解难以溶解的胺类1；有关胺 BNPA 盐分解的问题2

Sigma Aldrich - 292966

包装
5, 25 g in glass bottle

Toronto Research Chemicals - B387005

The S enantiomer of binaphthol derivative as chiral quenching agent.

Toronto Research Chemicals - B387000

The R enantiomer of binaphthol derivative as chiral quenching agent.

参考文献

• Strambini, G., et al.: Biochemistry, 29, 196 (1990)
• Gabellieri, E., et al.: Eur. J. Biochem., 221, 77 (1990)
• Cioni, P., et al.: Biophys. J., 86, 1149 (1990)
• Veldhuis, G., et al.: J. Biol. Chem., 280, 35148 (1990)
• Strambini, G., et al.: Biochemistry, 29, 196 (1990)
• Gabellieri, E., et al.: Eur. J. Biochem., 221, 77 (1990)
• Cioni, P., et al.: Biophys. J., 86, 1149 (1990)
• Veldhuis, G., et al.: J. Biol. Chem., 280, 35148 (1990)