(2S,3R,6S)-3,4-dimethyl-2-phenyl-1-oxa-4-azaspiro[5.5]undec-8-en-5-one | 889100-62-3

• 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,3R,6S)-3,4-dimethyl-2-phenyl-1-oxa-4-azaspiro[5.5]undec-8-en-5-one
• 英文别名: (2S,3R,6S)-3,4-dimethyl-2-phenyl-1-oxa-4-azaspiro[5.5]undec-9-en-5-one
• CAS: 889100-62-3
• 化学式: C₁₇H₂₁NO₂
• 分子量: 271.359
• InChiKey: GBGYNCAGDMMLNH-FRFSOERESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 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：

  (2S,3R,6S)-3,4-dimethyl-2-phenyl-1-oxa-4-azaspiro[5.5]undec-8-en-5-one 在 氨 、 sodium 、 N-溴代丁二酰亚胺(NBS) 作用下， 以 四氢呋喃 为溶剂， 反应 1.05h， 以54%的产率得到4-bromo-1-hydroxy-6-oxabicyclo[3.2.1]octan-7-one
  参考文献：
  名称：

  A Concise, Enantioselective Approach to (−)-Quinic Acid

  摘要：

  An expedient, enantioselective synthesis of a key precursor to (-)-quinic acid has been achieved from an ephedrine-derived morpholine-dione. The salient features of this approach are a highly diastereoselective conversion of the dione to a dialkenyl morpholinone and a subsequent ring-closing metathesis reaction. Removal of the ephedrine portion generates an enantiomerically enriched hydroxycyclohexene carboxamide that is readily converted to the quinic acid precursor.

  DOI：

  10.1021/ol060399h
• 作为产物：
  描述：

  盐酸右旋麻黄碱 在 4-二甲氨基吡啶 、 Grubbs catalyst first generation 、 四氯化钛 、 三乙胺 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 5.0h， 生成 (2S,3R,6S)-3,4-dimethyl-2-phenyl-1-oxa-4-azaspiro[5.5]undec-8-en-5-one
  参考文献：
  名称：

  A Concise, Enantioselective Approach to (−)-Quinic Acid

  摘要：

  An expedient, enantioselective synthesis of a key precursor to (-)-quinic acid has been achieved from an ephedrine-derived morpholine-dione. The salient features of this approach are a highly diastereoselective conversion of the dione to a dialkenyl morpholinone and a subsequent ring-closing metathesis reaction. Removal of the ephedrine portion generates an enantiomerically enriched hydroxycyclohexene carboxamide that is readily converted to the quinic acid precursor.

  DOI：

  10.1021/ol060399h

文献信息

• A Concise, Enantioselective Approach to (−)-Quinic Acid
  作者：Sunil V. Pansare、Vikrant A. Adsool

  DOI：10.1021/ol060399h

  日期：2006.5.1

  An expedient, enantioselective synthesis of a key precursor to (-)-quinic acid has been achieved from an ephedrine-derived morpholine-dione. The salient features of this approach are a highly diastereoselective conversion of the dione to a dialkenyl morpholinone and a subsequent ring-closing metathesis reaction. Removal of the ephedrine portion generates an enantiomerically enriched hydroxycyclohexene carboxamide that is readily converted to the quinic acid precursor.