(2S,3S,5R,6S)-5-phenyl-2,6,7-trimethyl-1,4-dioxa-7-azaspiro[2,5]octan-8-one | 916606-92-3

• 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,3S,5R,6S)-5-phenyl-2,6,7-trimethyl-1,4-dioxa-7-azaspiro[2,5]octan-8-one
• 英文别名: (3S,5R,6S)-2,6,7-Trimethyl-5-phenyl-1,4-dioxa-7-azaspiro[2.5]octan-8-one；(2S,3S,5R,6S)-2,6,7-trimethyl-5-phenyl-1,4-dioxa-7-azaspiro[2.5]octan-8-one
• CAS: 916606-92-3
• 化学式: C₁₄H₁₇NO₃
• 分子量: 247.294
• InChiKey: AWAXTBBENADGIH-WRZDFSGXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  42.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2S,3S,5R,6S)-5-phenyl-2,6,7-trimethyl-1,4-dioxa-7-azaspiro[2,5]octan-8-one 在 三氟化硼乙醚 、 sodium hydride 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 3.25h， 生成 (2S,5S,6R)-2-((R)-1-(3-methylbut-3-enyloxy)ethyl)-2-allyl-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
• 作为产物：
  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

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.