(2R)-2-(fluorodiphenylmethyl)pyrrolidine

• ChemBase编号: 150769
• 分子式: C17H18FN
• 平均质量: 255.3299232
• 单一同位素质量: 255.1423278
• SMILES: c1ccc(cc1)C(c1ccccc1)([C@H]1CCCN1)F
• Canonical SMILES: FC(c1ccccc1)(c1ccccc1)[C@H]1CCCN1
• InChI: InChI=1S/C17H18FN/c18-17(16-12-7-13-19-16,14-8-3-1-4-9-14)15-10-5-2-6-11-15/h1-6,8-11,16,19H,7,12-13H2/t16-/m1/s1
• InChIKey: PGKMVPFJFKOUDA-MRXNPFEDSA-N

名称和登记号

名称

• IUPAC标准名: (2R)-2-(fluorodiphenylmethyl)pyrrolidine
• IUPAC传统名: (2R)-2-(fluorodiphenylmethyl)pyrrolidine
• 别名: (R)-(+)-2-(氟二苯甲基)吡咯烷; (R)-(+)-2-(Fluorodiphenylmethyl)pyrrolidine

登记号

• CAS号: 352535-00-3
• PubChem SID: 24879278; 162244929
• PubChem CID: 16217115

理论计算性质

• 质子受体: 1
• 质子供体: 1
• LogD (pH = 5.5): 0.5979104
• LogD (pH = 7.4): 1.7104809
• Log P: 3.7674382
• 摩尔折射率: 75.4908 cm^3
• 极化性: 29.611492 Å^3
• 极化表面积: 12.03 Å^2
• 可自由旋转的化学键: 3
• 里宾斯基五规则: true

分子性质

理化性质

• 闪点: 145.4 °F; 63 °C
• 密度: 1.098 g/mL at 25 °C(lit.)
• 折射率: n20/D 1.577(lit.)
• 比旋光度: [α]20/D +25°, c = 1 in chloroform

安全信息

• 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
• 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
• 个人保护装置: Eyeshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter

产品相关信息

• 纯度: 97%
• 光学纯度: ee: 98% (HPLC)
• Empirical Formula (Hill Notation): C17H18FN

详细说明

Sigma Aldrich - 552550

包装
500 mg in glass bottle
Legal Information
英国 Onyx Scientific 产品
Application
Features:
• Highly efficient
• Excellent enantioselectivities
• Available in both enantiomers
• Operationally simple transformationsCatalyst for the enantioselective Weitz-Scheffer epoxidation of α,β-unsaturated aldehydes.1Condensation of this secondary amine with an aldehyde reversibly generates a β-fluoroiminium species where the fluorine atom is positioned gauche to the electropositive nitrogen centre.2Consequently, the phenyl substituents on the fluorine bearing carbon are placed in a predictable region of space. One of the groups effectively shields the upper face of the pendant iminium chain.Addition of hydrogen peroxide occurs in a highly selective manner to furnish optically enriched epoxides with excellent levels of enantiocontrol (Scheme 1).Simple α,β-disubstituted enals such as trans-cinnamaldehyde are smoothly converted to the corresponding epoxy aldehydes (up to 96% ee) as are their aliphatic analogues. The enantioselective, catalytic epoxidation of more challenging cyclic α,α,β-trisubstituted enals, and even an example of a α,α,β,β-tetrasubstituted enal, proceed with good yields and excellent enantioselectivities (up to 98% ee)3 (Scheme 2).