(1R,4R,6S)-4,7,7-Trimethyl-bicyclo[4.1.0]heptan-3-one O-(S)-1-oxiranylmethyl-oxime | 461388-87-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: (1R,4R,6S)-4,7,7-Trimethyl-bicyclo[4.1.0]heptan-3-one O-(S)-1-oxiranylmethyl-oxime
• CAS: 461388-87-4
• 化学式: C₁₃H₂₁NO₂
• 分子量: 223.315
• InChiKey: LNKILCFFCMWLDK-PNFDVCILSA-N

反应信息

• 作为反应物：
  描述：

  异丙胺 、 (1R,4R,6S)-4,7,7-Trimethyl-bicyclo[4.1.0]heptan-3-one O-(S)-1-oxiranylmethyl-oxime 在 盐酸 作用下， 以 乙醚 为溶剂， 反应 18.0h， 以67%的产率得到(1R,4R,6S)-4,7,7-Trimethyl-bicyclo[4.1.0]heptan-3-one O-((S)-2-hydroxy-3-isopropylamino-propyl)-oxime; hydrochloride
  参考文献：
  名称：

  Stereochemistry of terpene derivatives. Part 3: Hydrolytic kinetic resolution as a convenient approach to chiral aminohydroxyiminocaranes with local anaesthetic activity

  摘要：

  We have developed a stereoselective hydrolytic kinetic resolution process for diastereoisomeric mixtures of epoxy-iminocarene intermediates in the presence of (R,R)-(-)-(salen)Co(III)OAc catalyst, this was applied as the first step in the synthesis of novel chiral aminohydroxyiminocarane derivatives with local anaesthetic activity. The absolute configuration of the product was confirmed by X-ray crystallography. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00205-7
• 作为产物：
  描述：

  (1R,4R,6S)-4,7,7-Trimethyl-bicyclo[4.1.0]heptan-3-one O-((S)-2,3-dihydroxy-propyl)-oxime 在 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 苯 为溶剂， 反应 3.0h， 以71%的产率得到(1R,4R,6S)-4,7,7-Trimethyl-bicyclo[4.1.0]heptan-3-one O-(S)-1-oxiranylmethyl-oxime
  参考文献：
  名称：

  Stereochemistry of terpene derivatives. Part 3: Hydrolytic kinetic resolution as a convenient approach to chiral aminohydroxyiminocaranes with local anaesthetic activity

  摘要：

  We have developed a stereoselective hydrolytic kinetic resolution process for diastereoisomeric mixtures of epoxy-iminocarene intermediates in the presence of (R,R)-(-)-(salen)Co(III)OAc catalyst, this was applied as the first step in the synthesis of novel chiral aminohydroxyiminocarane derivatives with local anaesthetic activity. The absolute configuration of the product was confirmed by X-ray crystallography. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00205-7