(1R,2S,6R,7S)-1,10,10-trimethyl-5-oxido-4-propyl-3-oxa-5-azoniatricyclo[5.2.1.02,6]dec-4-ene | 154404-24-7

• 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-propyl-3-oxa-5-azoniatricyclo[5.2.1.02,6]dec-4-ene
• CAS: 154404-24-7
• 化学式: C₁₄H₂₃NO₂
• 分子量: 237.342
• InChiKey: CEBMHUPULCXGNT-LHMODEAPSA-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：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.93
• 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-propyl-3-oxa-5-azoniatricyclo[5.2.1.02,6]dec-4-ene 在 吡啶 、 lithium aluminium tetrahydride 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 81.0h， 生成 <2S-(2α,3β,3aα,4aβ,5α,8α,8aβ)>-Octahydro-3,5,10,10-tetramethyl-2,3a-dipropyl-5,8-methano-2H-isoxazolo<3,2-b>benzoxazole
  参考文献：
  名称：

  [2 + 3] Cycloadditions of Enantiomerically Pure Oxazoline N-Oxides: An Alternative to the Asymmetric Aldol Condensation

  摘要：

  A series of camphor-derived oxazoline N-oxides were obtained by condensation of the appropriate orthoesters with (+)-3-(hydroxyamino)borneol (8). These unstable dipoles were used without isolation in various [2 + 3] asymmetric cyclocondensations. The regio- and diastereoselectivities of these reactions were good to excellent. After functional group transformations, adducts were cleaved by a two--step sequence (i.e., oxidation followed by acidic hydrolysis) giving beta-hydroxy ketones and (+)-3-(hydroxyimino)borneol (19). Asymmetric synthesis of (+)-1,7-dioxaspiro[5.5]-undecan-4-ol, a pheromone of Dacus oleae, was achieved as an application of this new method.

  DOI：

  10.1021/jo00111a033
• 作为产物：
  描述：

  原丁酸三甲酯 、 (3-hydroxyamino)isoborneol hydrochloride 在 4 A molecular sieve 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 (1R,2S,6R,7S)-1,10,10-trimethyl-5-oxido-4-propyl-3-oxa-5-azoniatricyclo[5.2.1.02,6]dec-4-ene
  参考文献：
  名称：

  [2 + 3] Cycloadditions of Enantiomerically Pure Oxazoline N-Oxides: An Alternative to the Asymmetric Aldol Condensation

  摘要：

  A series of camphor-derived oxazoline N-oxides were obtained by condensation of the appropriate orthoesters with (+)-3-(hydroxyamino)borneol (8). These unstable dipoles were used without isolation in various [2 + 3] asymmetric cyclocondensations. The regio- and diastereoselectivities of these reactions were good to excellent. After functional group transformations, adducts were cleaved by a two--step sequence (i.e., oxidation followed by acidic hydrolysis) giving beta-hydroxy ketones and (+)-3-(hydroxyimino)borneol (19). Asymmetric synthesis of (+)-1,7-dioxaspiro[5.5]-undecan-4-ol, a pheromone of Dacus oleae, was achieved as an application of this new method.

  DOI：

  10.1021/jo00111a033

文献信息

• Oxazolines N-oxides as powerful dipoles in asymmetric [2+3] cycloadditions
  作者：T. Bérranger、C. André-Barrès、M. Kobayakawa、Y. Langlois

  DOI：10.1016/s0040-4039(00)60680-9

  日期：1993.8

  (+)-Norephedrine and (+)-camphor oxazolines N-oxides 9a, 9b and 13a, 13b underwent regio- and stereoselective [2+3] cycloadditions on various electron poor dipolarophiles.

  （+）-去氧麻黄碱和（+）-樟脑恶唑啉N-氧化物9a，9b和13a，13b在各种电子贫乏的双极性亲和剂上进行了区域选择性和立体选择性[2 + 3]环加成。
• [2 + 3] Cycloadditions of Enantiomerically Pure Oxazoline N-Oxides: An Alternative to the Asymmetric Aldol Condensation
  作者：Thierry Berranger、Yves Langlois

  DOI：10.1021/jo00111a033

  日期：1995.3

  A series of camphor-derived oxazoline N-oxides were obtained by condensation of the appropriate orthoesters with (+)-3-(hydroxyamino)borneol (8). These unstable dipoles were used without isolation in various [2 + 3] asymmetric cyclocondensations. The regio- and diastereoselectivities of these reactions were good to excellent. After functional group transformations, adducts were cleaved by a two--step sequence (i.e., oxidation followed by acidic hydrolysis) giving beta-hydroxy ketones and (+)-3-(hydroxyimino)borneol (19). Asymmetric synthesis of (+)-1,7-dioxaspiro[5.5]-undecan-4-ol, a pheromone of Dacus oleae, was achieved as an application of this new method.
• 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.