(4R,5R,2'E)-N-cinnamoyl-trans-hexahydrobenzoxazolidin-2-one | 872220-22-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (4R,5R,2'E)-N-cinnamoyl-trans-hexahydrobenzoxazolidin-2-one
• 英文别名: (3aR,7aR)-3-[(E)-3-phenylprop-2-enoyl]-3a,4,5,6,7,7a-hexahydro-1,3-benzoxazol-2-one
• CAS: 872220-22-9
• 化学式: C₁₆H₁₇NO₃
• 分子量: 271.316
• InChiKey: CQHSDSZFFKFCSM-SNESEAJLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (4R,5R,2'E)-N-cinnamoyl-trans-hexahydrobenzoxazolidin-2-one 、 丙基溴化镁 在 zinc(II) iodide 作用下， 以 四氢呋喃 为溶剂， 反应 2.33h， 以79%的产率得到
  参考文献：
  名称：

  Asymmetric Michael addition using N-cinnamoyl- and N-crotonyl-trans-hexahydrobenzoxazolidin-2-ones

  摘要：

  Preparation of N-cinnamoyl- and N-crotonyl-oxazolidin-2-ones 2 and 3 or ent-2 and ent-3 from (4S,5s)- and (4R,5R)trans-hexahydrobenzoxazolidin-2-ones 1 or ent-1 are reported. Stereoselective copper promoted conjugated additions of Grignard reagents to chiral N-enoyl amides 2 and 3 or ent-2 and ent-3 in the presence of Zn(II) salts afforded the 1,4-addition products 4-11 and the corresponding enantiomers. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.10.065
• 作为产物：
  描述：

  3-苯基-2-丙烯酰氯 、 trans-hexahydrobenzoxazolidin-2-one 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以80%的产率得到(4R,5R,2'E)-N-cinnamoyl-trans-hexahydrobenzoxazolidin-2-one
  参考文献：
  名称：

  Asymmetric Michael addition using N-cinnamoyl- and N-crotonyl-trans-hexahydrobenzoxazolidin-2-ones

  摘要：

  Preparation of N-cinnamoyl- and N-crotonyl-oxazolidin-2-ones 2 and 3 or ent-2 and ent-3 from (4S,5s)- and (4R,5R)trans-hexahydrobenzoxazolidin-2-ones 1 or ent-1 are reported. Stereoselective copper promoted conjugated additions of Grignard reagents to chiral N-enoyl amides 2 and 3 or ent-2 and ent-3 in the presence of Zn(II) salts afforded the 1,4-addition products 4-11 and the corresponding enantiomers. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.10.065

文献信息

• Asymmetric Michael addition using N-cinnamoyl- and N-crotonyl-trans-hexahydrobenzoxazolidin-2-ones
  作者：Lydia Pérez、Sylvain Bernès、Leticia Quintero、Cecilia Anaya de Parrodi

  DOI：10.1016/j.tetlet.2005.10.065

  日期：2005.12

  Preparation of N-cinnamoyl- and N-crotonyl-oxazolidin-2-ones 2 and 3 or ent-2 and ent-3 from (4S,5s)- and (4R,5R)trans-hexahydrobenzoxazolidin-2-ones 1 or ent-1 are reported. Stereoselective copper promoted conjugated additions of Grignard reagents to chiral N-enoyl amides 2 and 3 or ent-2 and ent-3 in the presence of Zn(II) salts afforded the 1,4-addition products 4-11 and the corresponding enantiomers. (c) 2005 Elsevier Ltd. All rights reserved.