-4-(1-methylethyl)-3-(2-methyl-1-oxo-3-phenyl-2-propenyl)-2-oxazolidinone | 136057-73-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: -4-(1-methylethyl)-3-(2-methyl-1-oxo-3-phenyl-2-propenyl)-2-oxazolidinone
• 英文别名: (4S)-3-[(E)-2-methyl-3-phenylprop-2-enoyl]-4-propan-2-yl-1,3-oxazolidin-2-one
• CAS: 136057-73-3
• 化学式: C₁₆H₁₉NO₃
• 分子量: 273.332
• InChiKey: LWEVSZYDHMKQNN-BRADTZPFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.09
• 重原子数：
  20.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  46.61
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  -4-(1-methylethyl)-3-(2-methyl-1-oxo-3-phenyl-2-propenyl)-2-oxazolidinone 在 lithium aluminium tetrahydride 、 正丁基锂 作用下， 以 乙醚 为溶剂， 反应 5.0h， 生成
  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
• 作为产物：
  描述：

  (E)-2-methyl-3-phenylacryloyl chloride 、 (S)-4-异丙基-2-唑烷酮 在 正丁基锂 作用下， 生成 -4-(1-methylethyl)-3-(2-methyl-1-oxo-3-phenyl-2-propenyl)-2-oxazolidinone
  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。