(4S)-3-[(2R,3R)-2-methyl-3-phenyl-3-phenylsulfanylpropanoyl]-4-propan-2-yl-1,3-oxazolidin-2-one | 136088-22-7

• 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: (4S)-3-[(2R,3R)-2-methyl-3-phenyl-3-phenylsulfanylpropanoyl]-4-propan-2-yl-1,3-oxazolidin-2-one
• CAS: 136088-22-7
• 化学式: C₂₂H₂₅NO₃S
• 分子量: 383.511
• InChiKey: LUWMHHRYOQHBOD-PWIZWCRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  71.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (E)-2-methyl-3-phenylacryloyl chloride 在 正丁基锂 作用下， 反应 5.0h， 生成 (4S)-3-[(2R,3R)-2-methyl-3-phenyl-3-phenylsulfanylpropanoyl]-4-propan-2-yl-1,3-oxazolidin-2-one
  参考文献：
  名称：

  Asymmetric construction of two contiguous stereocenters by diastereoface differentiating addition reaction of thiols to chiral imides: Formal synthesis of (+)-diltiazem

  摘要：

  A high degree of diastereoselectivity has been achieved on the asymmetric construction of two contiguous stereocenters by the conjugate addition of thiols to alpha,beta-unsaturated imides possessing Evans's chiral auxiliary. Addition reactions of thiophenol to chiral E- and Z-2-methylcrotonyl imides 4 proceeded with high diastereoface selectivities. Diastereoselectivities were discussed when E- and Z-imides 4 and 5 were used as the substrates. A successful application was demonstrated by the formal synthesis of a clinically useful cardiac drug, (+)-diltiazem. (C) 1997, Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(96)01191-x

文献信息

• Asymmetric induction at two contiguous stereogenic centers by diastereoface differentiating nucleophilic addition reaction
  作者：Okiko Miyata、Tetsuro Shinada、Ichiya Ninomiya、Takeaki Naito

  DOI：10.1016/0040-4039(91)80821-m

  日期：1991.7

  Distereoface differentiating nucleophilic of thiophenol to olefins delivers a new concomitant asymmetric construction of two contiguous stereogenic centers and has been successfully applied to the asymmetric synthesis of (+)-diltiazem.

  Distereoface区分苯酚与苯酚的亲核性，提供了一个新的伴随的两个不连续立体中心的不对称结构，并已成功地应用于（+）-地尔硫m的不对称合成。
• Asymmetric construction of two contiguous stereocenters by diastereoface differentiating addition reaction of thiols to chiral imides: Formal synthesis of (+)-diltiazem
  作者：Okiko Miyata、Tetsuro Shinada、Ichiya Ninomiya、Takeaki Naito

  DOI：10.1016/s0040-4020(96)01191-x

  日期：1997.2

  A high degree of diastereoselectivity has been achieved on the asymmetric construction of two contiguous stereocenters by the conjugate addition of thiols to alpha,beta-unsaturated imides possessing Evans's chiral auxiliary. Addition reactions of thiophenol to chiral E- and Z-2-methylcrotonyl imides 4 proceeded with high diastereoface selectivities. Diastereoselectivities were discussed when E- and Z-imides 4 and 5 were used as the substrates. A successful application was demonstrated by the formal synthesis of a clinically useful cardiac drug, (+)-diltiazem. (C) 1997, Elsevier Science Ltd.