(2S,5S,6R)-2-allyl-2-((S)-1-(allyloxy)ethyl)-4,5-dimethyl-6-phenylmorpholin-3-one | 916606-94-5

• 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: (2S,5S,6R)-2-allyl-2-((S)-1-(allyloxy)ethyl)-4,5-dimethyl-6-phenylmorpholin-3-one
• 英文别名: (2S,5S,6R)-4,5-dimethyl-6-phenyl-2-[(1S)-1-prop-2-enoxyethyl]-2-prop-2-enylmorpholin-3-one
• CAS: 916606-94-5
• 化学式: C₂₀H₂₇NO₃
• 分子量: 329.439
• InChiKey: XMZFPMGAXUQBJE-DUPRYPCISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2S,5S,6R)-2-allyl-2-((S)-1-(allyloxy)ethyl)-4,5-dimethyl-6-phenylmorpholin-3-one 在 Grubbs catalyst first generation 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 以70%的产率得到(2R,3S,6S,7S)-2-phenyl-3,4,7-trimethyl-1,8-dioxa-4-azaspiro[5.6]dodec-10-en-5-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：

  (Z,5S,6R)-2-ethylidene-4,5-dimethyl-6-phenylmorpholin-3-one 在 三氟化硼乙醚 、 potassium hydride 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 4.5h， 生成 (2S,5S,6R)-2-allyl-2-((S)-1-(allyloxy)ethyl)-4,5-dimethyl-6-phenylmorpholin-3-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

文献信息

• 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.