(3aR)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole

• ChemBase编号: 125073
• 分子式: C18H20BNO
• 平均质量: 277.1685
• 单一同位素质量: 277.16379467
• SMILES: O1B(N2CCC[C@@H]2C1(c1ccccc1)c1ccccc1)C
• Canonical SMILES: CB1OC([C@@H]2N1CCC2)(c1ccccc1)c1ccccc1
• InChI: InChI=1S/C18H20BNO/c1-19-20-14-8-13-17(20)18(21-19,15-9-4-2-5-10-15)16-11-6-3-7-12-16/h2-7,9-12,17H,8,13-14H2,1H3/t17-/m1/s1
• InChIKey: VMKAFJQFKBASMU-QGZVFWFLSA-N

名称和登记号

名称

• IUPAC标准名: (3aR)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole
• IUPAC传统名: (3aR)-1-methyl-3,3-diphenyl-tetrahydropyrrolo[1,2-c][1,3,2]oxazaborole
• 别名: (R)-(+)-2-甲基-CBS-噁唑硼烷; α,α-二苯基-D-脯氨醇甲基硼酸环酰胺酯; (R)-2-甲基-CBS-噁唑硼烷; (R)-四氢-1-甲基-3,3-二苯基-1H,3H-吡咯并[1,2-c][1,3,2]噁唑硼烷; (R)-1-甲基,3,3-二苯基-四氢-吡咯并(1,2-c)(1,3,2)噁唑硼烷; (R)-3-甲基-CBS-氧杂硼啶; (R)-(+)-2-甲基-CBS-噁唑硼烷 溶液; (R)-2-甲基-CBS-氧杂硼啶单水合物; (R)-2-甲基-CBS-氧杂硼啶, 1M 甲苯溶液; (R)-(+)-2-Methyl-CBS-oxazaborolidine; α,α-Diphenyl-D-prolinol methylboronic acid cycl-amide-ester; (R)-3,3-Diphenyl-1-methyltetrahydro-3H-pyrrolo[1,2-c][1,3,2]oxazaborole; (R)-Methyl oxazaborolidine; (R)-(+)-2-methyl-CBS-oxazaborolidine; (R)-2-Methyl-CBS-oxazaborolidine; α,α-Diphenyl-D-prolinolmethylboronic acid cyclamide ester; (R)-1-Methyl,3,3-diphenyl-tetrahydro-pyrrolo(1,2-c)(1,3,2)oxazaborole; (R)-Tetrahydro-1-methyl-3,3-diphenyl-1H,3H-pyrrolo[1,2-c][1,3,2]oxazaborole; (R)-(+)-2-Methyl-CBS-oxazaborolidine solution; (R)-3,3-Diphenyl-1-methylpyrrolidino[1,2-c]-1,3,2-oxazaborole; (R)-2-Methyl-CBS-oxazaborolidine monohydrate; (R)-2-Methyl-CBS-oxazaborolidine, 1M soln. in toluene

登记号

• CAS号: 112022-83-0
• MDL号: MFCD00078440
• Beilstein号: 9059874
• PubChem SID: 162219423; 24869385; 24867003; 24883644; 24885228
• PubChem CID: 9838490
• Chemspider ID: 8014210
• 维基百科标题: (R)-2-Methyl-CBS-oxazaborolidine

理论计算性质

• 质子受体: 2
• 质子供体: 0
• LogD (pH = 5.5): 4.2477818
• LogD (pH = 7.4): 4.4010496
• Log P: 4.4034
• 摩尔折射率: 81.1142 cm^3
• 极化性: 33.783737 Å^3
• 极化表面积: 12.47 Å^2
• 可自由旋转的化学键: 2
• 里宾斯基五规则: true

分子性质

理化性质

• 外观: Colorless to pale yellow liquid (in toluene)
• 熔点: 77-82 °C; 85-95 °C; 85-95 °C(lit.)
• 沸点: 111 °C
• 闪点: 1.4 °F; -17 °C; 39.2 °F; 4 °C; 4°C(39°F)
• 密度: 0.925; 0.942 g/mL at 25 °C; 0.95 g/mL; 0.95 g/mL at 25 °C
• 折射率: n20/D 1.4602
• 比旋光度: [α]20/546 +43±3°, c = 1% in methanol; [α]22/D +76.8°, c = 1 in toluene; +74 (c=1 in methanol)

安全信息

• 保存注意事项: Air & Moisture Sensitive
• 欧盟危险性物质标志: 易燃性(Flammable) (F); X; 刺激性(Irritant) (Xi); 有害性(Harmful) (Xn)
• 联合国危险货物编号: 1294; 2056; UN1993
• 德国WGK号: 3
• 联合国危险货物等级: 3
• 联合国危险货物包装类别(PG): 2; II
• 危险公开号: 11-19-36/37; 11-20-38-48/20-63-65-67; 63-11-38-48/20-65-67; R17
• 安全公开号: 16-26; 16-36/37-62; 36/37-46-62
• TSCA收录: 否
• GHS危险品标识: GHS02; GHS07; GHS08
• GHS警示词: Danger
• GHS危险声明: H224-H304-H361-H373-H332-H315-H336; H225-H304-H315-H336-H361d-H373; H225-H319-H335
• GHS警示性声明: P210-P241-P301+P310-P303+P361+P353-P405-P501A; P210-P261-P281-P301 + P310-P331; P210-P261-P305 + P351 + P338
• 个人保护装置: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter; Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• RID/ADR: UN 1294 3/PG 2; UN 2056 3/PG 2
• 欧盟补充危害声明: May form explosive peroxides.
• 保存温度: 2-8°C; room temp

产品相关信息

• 纯度: ≥95%; ≥95.0% (HPLC); 94%
• 浓度: 1 M in THF; 1 M in toluene; 1M soln. in toluene
• Empirical Formula (Hill Notation): C18H20BNO

详细说明

Sigma Aldrich - 649317

包装
1, 10 g in glass bottle
Application
CBS Catalysts for Asymmetric Reduction and Asymmetric Synthesis
CBS (Corey-Bakshi-Shibata) 噁唑硼烷催化剂已被用于前手性酮的非对称性还原。其他应用包括 α-羟基酸、α-氨基酸、C2 对称二茂铁二醇以及炔丙醇的对映选择性合成。

Sigma Aldrich - 674656

包装
5, 25 mL in glass bottle
Application
CBS Catalysts for Asymmetric Reduction and Asymmetric Synthesis
CBS (Corey-Bakshi-Shibata) 噁唑硼烷催化剂已被用于前手性酮的非对称性还原。其他应用包括 α-羟基酸、α-氨基酸、C2 对称二茂铁二醇以及炔丙醇的对映选择性合成。

Sigma Aldrich - 457698

包装
25 mL in Sure/Seal™
5 mL in glass bottle
Physical form
储存时可能形成沉淀，但不影响产品质量。在惰性气体环境下将产品缓慢加热至 80-90°C，使固体再溶解。
Application
CBS Catalysts for Asymmetric Reduction and Asymmetric Synthesis
CBS (Corey-Bakshi-Shibata) 噁唑硼烷催化剂已被用于前手性酮的非对称性还原。其他应用包括 α-羟基酸、α-氨基酸、C2 对称二茂铁二醇以及炔丙醇的对映选择性合成。 用于去对称化还原反应，生成 (S)-4-羟基环己酮。

参考文献

• Anhydrous catalyst for CBS reduction reaction. For further information, see (S)-2-Methyl-CBS-oxazaborolidine monohydrate, L09219.
• Air-stable solid prepared by a modification of Corey's procedure, on which his literature results were based. For anhydrous reagent, see (R)-2-Methyl-CBS-oxazaborolidine, L14582.
• Chiral auxiliary for the highly enantioselective reduction of prochiral ketones, see (S)-2-Methyl-CBS-oxazaborolidine monohydrate, L09219.