tert-butyl (4R)-4-[[(1R)-2-hydroxy-1-phenylethyl]amino]-2-methylidene-4-phenylbutanoate | 142292-45-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: tert-butyl (4R)-4-[[(1R)-2-hydroxy-1-phenylethyl]amino]-2-methylidene-4-phenylbutanoate
• CAS: 142292-45-3
• 化学式: C₂₃H₂₉NO₃
• 分子量: 367.488
• InChiKey: FZDBKOAMXPRFGS-RTWAWAEBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  27
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  58.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  tert-butyl (4R)-4-[[(1R)-2-hydroxy-1-phenylethyl]amino]-2-methylidene-4-phenylbutanoate 在 盐酸 、 氯化亚砜 、 硫酸 、 四丁基硫酸氢铵 、 silica gel 、 甲基磺酰氯 、 三乙胺 作用下， 以 硝基甲烷 为溶剂， 生成 (-)-(R)-3-methylene-5-phenylpyrrolidin-2-one
  参考文献：
  名称：

  Stereocontrolled preparation of chiral secondary α-methylene γ-lactams by addition of organozinc reagents derived from 2-(bromomethy])acrylates to imines using β-aminoalcohols as chiral auxiliaries.

  摘要：

  Stereocontrolled addition of isolated organozinc reagents 1, prepared from 2-(bromomethyl)acrylates to imines, can be achieved with d.e. approximately 100% using beta-amino alcohols as chiral auxiliaries. High yields of pure R or S secondary alpha-methylene gamma-lactams can be prepared after a three step elimination of the chiral auxiliary (chloration, dehydrochloration of the resulting beta-chloroamine, acid hydrolysis of enamide).

  DOI：

  10.1016/s0957-4166(00)80253-0
• 作为产物：
  描述：

  β-[(phenylmethylene)amino]-[R-(E)-]-benzeneethanol 、 以86%的产率得到tert-butyl (4R)-4-[[(1R)-2-hydroxy-1-phenylethyl]amino]-2-methylidene-4-phenylbutanoate
  参考文献：
  名称：

  Stereocontrolled preparation of chiral secondary α-methylene γ-lactams by addition of organozinc reagents derived from 2-(bromomethy])acrylates to imines using β-aminoalcohols as chiral auxiliaries.

  摘要：

  Stereocontrolled addition of isolated organozinc reagents 1, prepared from 2-(bromomethyl)acrylates to imines, can be achieved with d.e. approximately 100% using beta-amino alcohols as chiral auxiliaries. High yields of pure R or S secondary alpha-methylene gamma-lactams can be prepared after a three step elimination of the chiral auxiliary (chloration, dehydrochloration of the resulting beta-chloroamine, acid hydrolysis of enamide).

  DOI：

  10.1016/s0957-4166(00)80253-0