(Z,5S,6R)-2-ethylidene-4,5-dimethyl-6-phenylmorpholin-3-one | 207223-30-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 恶嗪烷类
• 英文名称: (Z,5S,6R)-2-ethylidene-4,5-dimethyl-6-phenylmorpholin-3-one
• 英文别名: (2Z,5S,6R)-2-ethylidene-4,5-dimethyl-6-phenylmorpholin-3-one
• CAS: 207223-30-1
• 化学式: C₁₄H₁₇NO₂
• 分子量: 231.294
• InChiKey: KUDLLYRKGCQZFH-MLTCVSMMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (Z,5S,6R)-2-ethylidene-4,5-dimethyl-6-phenylmorpholin-3-one 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.75h， 以80%的产率得到(2S,3S,5R,6S)-5-phenyl-2,6,7-trimethyl-1,4-dioxa-7-azaspiro[2,5]octan-8-one
  参考文献：
  名称：

  Enantioselective Synthesis of Functionalized Medium-Sized Oxacycles

  摘要：

  Enantioselective routes to functionalized, seven-, eight-, and nine-membered oxacycles that are amenable to further elaboration have been developed. Salient features of the methodology include highly diastereoselective and regioselective transformations of an ephedrine-derived epoxy morpholinone to functionalized precursors of the oxacycles. The ephedrine scaffold exerts remote stereocontrol in the functionalization of the appended oxacycle.

  DOI：

  10.1021/ol062484v
• 作为产物：
  描述：

  2S,5S,6R-2-ethyl-4,5-dimethyl-2-hydroxy-6-phenyl-morpholin-3-one 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 生成 (Z,5S,6R)-2-ethylidene-4,5-dimethyl-6-phenylmorpholin-3-one
  参考文献：
  名称：

  Stereoselective synthesis of α-hydroxycyclopropanecarboxylic acids

  摘要：

  Cyclopropanation of chiral alpha-alkoxy acrylamides derived from 1R,2S-ephedrine and alpha-keto acids provides cyclopropyl morpholinones with good diastereoselectivity. Removal of the ephedrine portion generates alpha-hydroxycyclopropane carboxamides which are readily converted to enantiomerically enriched alpha-hydroxycyclopropanecarboxylic acids. (C) 1999 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)00233-6

文献信息

• Asymmetric Allylation and Reduction on an Ephedrine-Derived Template:  Stereoselective Synthesis of α-Hydroxy Acids and Derivatives
  作者：Sunil V. Pansare、R. Gnana Ravi、Rajendra P. Jain

  DOI：10.1021/jo9722820

  日期：1998.6.1
• Stereoselective synthesis of α-hydroxycyclopropanecarboxylic acids
  作者：Sunil V. Pansare、Rajendra P. Jain

  DOI：10.1016/s0040-4039(99)00233-6

  日期：1999.3

  Cyclopropanation of chiral alpha-alkoxy acrylamides derived from 1R,2S-ephedrine and alpha-keto acids provides cyclopropyl morpholinones with good diastereoselectivity. Removal of the ephedrine portion generates alpha-hydroxycyclopropane carboxamides which are readily converted to enantiomerically enriched alpha-hydroxycyclopropanecarboxylic acids. (C) 1999 Published by Elsevier Science Ltd. All rights reserved.
• Enantioselective Synthesis of Functionalized Medium-Sized Oxacycles
  作者：Sunil V. Pansare、Vikrant A. Adsool

  DOI：10.1021/ol062484v

  日期：2006.12.1

  Enantioselective routes to functionalized, seven-, eight-, and nine-membered oxacycles that are amenable to further elaboration have been developed. Salient features of the methodology include highly diastereoselective and regioselective transformations of an ephedrine-derived epoxy morpholinone to functionalized precursors of the oxacycles. The ephedrine scaffold exerts remote stereocontrol in the functionalization of the appended oxacycle.