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

• ChemBase编号: 141220
• 分子式: C18H20BNO
• 平均质量: 277.1685
• 单一同位素质量: 277.16379467
• SMILES: B1(N2CCC[C@H]2C(O1)(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-/m0/s1
• InChIKey: VMKAFJQFKBASMU-KRWDZBQOSA-N

名称和登记号

名称

• IUPAC标准名: (3aS)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole
• IUPAC传统名: (3aS)-1-methyl-3,3-diphenyl-tetrahydropyrrolo[1,2-c][1,3,2]oxazaborole
• 别名: (S)-(-)-2-甲基-CBS-噁唑硼烷; α,α-二苯基-L-脯氨醇甲基硼酸环胺酯; (S)-3,3-二苯基-1-甲基四氢-3H-吡咯并[1,2-c][1,3,2]噁唑硼烷; (S)-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; (S)-1-甲基-3,3-二苯基-四氢-吡咯并[1,2c][1,3,2]噁唑硼烷; (S)-(-)-2-甲基-CBS-噁唑硼烷 溶液; (S)-2-甲基-CBS-氧杂硼啶单水合物; (S)-2-甲基-CBS-氧杂硼啶, 1M 甲苯溶液; (S)-(-)-2-Methyl-CBS-oxazaborolidine; α,α-Diphenyl-L-prolinol methylboronic acid cycl-amide ester; (S)-1-Methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2c][1,3,2]oxazaborole; (S)-3,3-Diphenyl-1-methyltetrahydro-3H-pyrrolo[1,2-c][1,3,2]oxazaborole; (S)-Tetrahydro-1-methyl-3,3-diphenyl-1H,3H-pyrrolo[1,2-c][1,3,2]oxazaborole; (S)-(-)-2-Methyl-CBS-oxazaborolidine solution; (S)-3,3-Diphenyl-1-methylpyrrolidino[1,2-c]-1,3,2-oxazaborole; (S)-2-Methyl-CBS-oxazaborolidine monohydrate; (S)-2-Methyl-CBS-oxazaborolidine, 1M soln. in toluene

登记号

• CAS号: 112022-81-8
• MDL号: MFCD00078439
• Beilstein号: 8492123
• PubChem SID: 24883643; 162235455; 24885227; 24869386
• PubChem CID: 2734713

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

• 熔点: 115-121°C
• 沸点: 111 °C
• 闪点: -15 °C; 39.2 °F; 4 °C; 4°C(39°F); 5 °F
• 密度: 0.925; 0.929 g/mL at 25 °C; 0.942 g/mL at 25 °C
• 折射率: n20/D 1.460
• 比旋光度: -67 (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: 11-19-36/37/38; 11-20-38-48/20-63-65-67; 36/37/38; 63-11-36/37/38-48/20-65-67
• 安全公开号: 16-26; 16-26-36/37-62; 26; 36/37-46-62
• TSCA收录: 否
• GHS危险品标识: GHS02; GHS07; GHS08
• GHS警示词: Danger; Warning
• GHS危险声明: H224-H304-H361-H373-H332-H315-H336; H225-H304-H315-H319-H335-H336-H361d-H373; H225-H315-H319-H335; H315-H319-H335
• GHS警示性声明: P210-P241-P301+P310-P303+P361+P353-P405-P501A; P210-P261-P281-P301 + P310-P305 + P351 + P338-P331; P210-P261-P305 + P351 + P338; P261-P305 + P351 + P338
• 个人保护装置: dust mask type N95 (US), Eyeshields, Gloves; Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) 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: room temp

产品相关信息

• 纯度: ≥95.0%; 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 - 674648

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 - 457701

包装
25 mL in Sure/Seal™
5 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 - 649309

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。

参考文献

• Anhydrous catalyst for 'CBS' reduction reaction. For examples of use in asymmetric reduction of ketones, see: Org. Synth. Coll., 9, 362, 676 (1998). 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 (S)-2-Methyl-CBS-oxazaborolidine, L14583.
• Catalyst for the CBS (Corey, Bakshi, Shibata) reduction of prochiral ketones with borane-THF, with high enantioselectivity (see (S)-(-)-ɑ,ɑ-Diphenylprolinol, L09217): J. Am . Chem. Soc., 109, 7925 (1987):
  
• For successful use of this system in a scaled up asymmetric synthesis of the antiarrythmia agent d-Sotalol, see: Org. Process Res. Dev., 1. 176 (1997). For use in enantioselective reduction of ketones containing heteroatoms, see: Tetrahedron Lett., 34, 785 (1993). For the asymmetric reduction of ɑ-ketoimines, see: Tetrahedron Lett., 35, 5551 (1994).
• For reviews of oxazaborolidines as enantioselective catalysts, see: Angew. Chem. Int. Ed., 31, 729 (1992); 37, 1986 (1998); Tetrahedron: Asymmetry, 3, 1475 (1992).
• For reviews of the asymmetric reduction of ketones, see: Synthesis, 605 (1992); Chem. Ind. (London), 552 (1994).