(1R,2S,6R,7S)-1,10,10-trimethyl-5-oxido-4-(2-phenylethyl)-3-oxa-5-azoniatricyclo[5.2.1.02,6]dec-4-ene | 206438-90-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (1R,2S,6R,7S)-1,10,10-trimethyl-5-oxido-4-(2-phenylethyl)-3-oxa-5-azoniatricyclo[5.2.1.02,6]dec-4-ene
• CAS: 206438-90-6
• 化学式: C₁₉H₂₅NO₂
• 分子量: 299.413
• InChiKey: WWWIVUZPSPXZEU-MYZZLAAOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  38
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1R,2S,6R,7S)-1,10,10-trimethyl-5-oxido-4-(2-phenylethyl)-3-oxa-5-azoniatricyclo[5.2.1.02,6]dec-4-ene 在 4-二甲氨基吡啶 、 sodium hydroxide 、 碳酸氢钠 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 49.0h， 生成 D-3-苯乳酸
  参考文献：
  名称：

  Stereoselective hetero-Claisen rearrangement of camphor derived oxazoline-N-oxides

  摘要：

  Camphor derived oxazoline-hi-oxides in the presence of various acylating agents afforded alpha-acyloxyoxazolines resulting from a diastereoselective [3,3] rearrangement. The configuration of the newly formed asymmetric center was established by chemical correlation. The observed diastereoselectivity accounts a concerted rather than a stepwise process. (C) 1998 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)00062-8
• 作为产物：
  描述：

  trimethyl 3-phenylorthopropanoate 、 (3-hydroxyamino)isoborneol hydrochloride 在 calcium carbonate 作用下， 以 甲苯 为溶剂， 反应 3.0h， 生成 (1R,2S,6R,7S)-1,10,10-trimethyl-5-oxido-4-(2-phenylethyl)-3-oxa-5-azoniatricyclo[5.2.1.02,6]dec-4-ene
  参考文献：
  名称：

  Stereoselective hetero-Claisen rearrangement of camphor derived oxazoline-N-oxides

  摘要：

  Camphor derived oxazoline-hi-oxides in the presence of various acylating agents afforded alpha-acyloxyoxazolines resulting from a diastereoselective [3,3] rearrangement. The configuration of the newly formed asymmetric center was established by chemical correlation. The observed diastereoselectivity accounts a concerted rather than a stepwise process. (C) 1998 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)00062-8

文献信息

• Stereoselective hetero-Claisen rearrangement of camphor derived oxazoline-N-oxides
  作者：Peter I. Dalko、Yves Langlois

  DOI：10.1016/s0040-4039(98)00062-8

  日期：1998.4

  Camphor derived oxazoline-hi-oxides in the presence of various acylating agents afforded alpha-acyloxyoxazolines resulting from a diastereoselective [3,3] rearrangement. The configuration of the newly formed asymmetric center was established by chemical correlation. The observed diastereoselectivity accounts a concerted rather than a stepwise process. (C) 1998 Published by Elsevier Science Ltd. All rights reserved.