(S)-[1-(1,1-dioxo-1H-1λ⁶-benzo[b]thiophen-2-yl)-2-phenylpropyl]carbamic acid benzyl ester

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (S)-[1-(1,1-dioxo-1H-1λ⁶-benzo[b]thiophen-2-yl)-2-phenylpropyl]carbamic acid benzyl ester
• 英文别名: benzyl N-[(1S)-1-(1,1-dioxo-1-benzothiophen-2-yl)-3-phenylpropyl]carbamate
• 化学式: C₂₅H₂₃NO₄S
• 分子量: 433.528
• InChiKey: HJFISYCBGAQVBD-QFIPXVFZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  31
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  80.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  benzothiophen-2-yllithium 、 氯甲酸苄酯 、 hydrocinnamaldehyde SAMP-hydrazone 生成 (S)-[1-(1,1-dioxo-1H-1λ⁶-benzo[b]thiophen-2-yl)-2-phenylpropyl]carbamic acid benzyl ester 、
  参考文献：
  名称：

  Asymmetric Synthesis of Heterocyclic β-Aminosulfones via Nucleophilic 1,2-Addition of 2-Lithiobenzo[b]thiophene to Aldehyde-SAMP-hydrazones

  摘要：

  An efficient asymmetric synthesis of alpha-(1,1-dioxo-2,3-dihydro-1H-1lambda(6)-benzo[b]thiophen-2-yl)-substituted amines is described. Key steps of the synthesis are the nucleophilic 1,2-addition of 2-lithio-benzo[b]thiophene to aldehyde-SAMP-hydrazones, a benzo[b]thiophene oxidation using dimethyldioxirane and a highly diastereoselective conjugate reduction with L-Selectride(R). The heterocyclic beta-aminosulfones are obtained in five steps and good overall yields (23-49%) and very high diastereo-and enantiomeric excesses (de greater than or equal to 96%, ee = 88-99%).

  DOI：

  10.3987/com-04-s(p)3

文献信息

• Asymmetric Synthesis of Heterocyclic β-Aminosulfones via Nucleophilic 1,2-Addition of 2-Lithiobenzo[b]thiophene to Aldehyde-SAMP-hydrazones
  作者：Dieter Enders、Giuseppe Del Signore

  DOI：10.3987/com-04-s(p)3

  日期：——

  An efficient asymmetric synthesis of alpha-(1,1-dioxo-2,3-dihydro-1H-1lambda(6)-benzo[b]thiophen-2-yl)-substituted amines is described. Key steps of the synthesis are the nucleophilic 1,2-addition of 2-lithio-benzo[b]thiophene to aldehyde-SAMP-hydrazones, a benzo[b]thiophene oxidation using dimethyldioxirane and a highly diastereoselective conjugate reduction with L-Selectride(R). The heterocyclic beta-aminosulfones are obtained in five steps and good overall yields (23-49%) and very high diastereo-and enantiomeric excesses (de greater than or equal to 96%, ee = 88-99%).