(1R,4S,6S)-4-isopropenyl-1-methyl-7-azabicyclo-[4.1.0]heptane | 849065-25-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氮杂环庚烷
• 英文名称: (1R,4S,6S)-4-isopropenyl-1-methyl-7-azabicyclo-[4.1.0]heptane
• 英文别名: (1R,4S,6S)-methyl-4-(prop-1-en-2-yl)-7-aza-bicyclo-[4.1.0]heptane；(1R,4S,6S)-1-Methyl-4-(prop-1-en-2-yl)-7-azabicyclo[4.1.0]heptane；(1R,4S,6S)-1-methyl-4-prop-1-en-2-yl-7-azabicyclo[4.1.0]heptane
• CAS: 849065-25-4
• 化学式: C₁₀H₁₇N
• 分子量: 151.252
• InChiKey: VZDOAGOKIUOLFX-LPEHRKFASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  21.9
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (1R,4S,6S)-4-isopropenyl-1-methyl-7-azabicyclo-[4.1.0]heptane 在 sodium azide 、 cerium(III) chloride heptahydrate 作用下， 以 水 、 乙腈 为溶剂， 反应 12.0h， 以71%的产率得到(2-azido-4-isopropenyl-1-methylcyclohexyl)amine
  参考文献：
  名称：

  A convenient synthesis of new diamine, amino alcohol and aminophosphines chiral auxiliaries based on limonene oxide

  摘要：

  A strategy for the synthesis of new chiral auxiliaries based upon vicinal diamines, amino alcohols and aminophosphines, obtained from limonene oxide, has been developed. The methodology allows the preparation of (1R,2R,4S)-1-methyl-4-(prop-1-en-2-yl)cyclohexane-1,2-diamine starting from a commercially available mixture of cis/trans (4S)-(-)-limonene oxides, through a stereoconvergent synthetic sequence. The process starts from an inexpensive naturally occurring material, is amenable to scale-up and allows easy access to highly useful enantiopure building blocks and ligands, employed in asymmetric catalysis. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.08.012
• 作为产物：
  描述：

  (1R,2R,5S)-2-azido-2-methyl-5-(prop-1-en-2-yl)cyclohexanol 在 三苯基膦 作用下， 以 1,4-二氧六环 为溶剂， 反应 24.0h， 以77%的产率得到(1R,4S,6S)-4-isopropenyl-1-methyl-7-azabicyclo-[4.1.0]heptane
  参考文献：
  名称：

  A convenient synthesis of new diamine, amino alcohol and aminophosphines chiral auxiliaries based on limonene oxide

  摘要：

  A strategy for the synthesis of new chiral auxiliaries based upon vicinal diamines, amino alcohols and aminophosphines, obtained from limonene oxide, has been developed. The methodology allows the preparation of (1R,2R,4S)-1-methyl-4-(prop-1-en-2-yl)cyclohexane-1,2-diamine starting from a commercially available mixture of cis/trans (4S)-(-)-limonene oxides, through a stereoconvergent synthetic sequence. The process starts from an inexpensive naturally occurring material, is amenable to scale-up and allows easy access to highly useful enantiopure building blocks and ligands, employed in asymmetric catalysis. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.08.012

文献信息

• Regio- and diastereoselective synthesis of bifunctionalized limonenes
  作者：Michael V. Voronkov、Ramanaiah C. Kanamarlapudi、Paul Richardson

  DOI：10.1016/j.tetlet.2005.08.009

  日期：2005.10

  High regio- and diastereoselective ring opening of limonene aziridines with a variety of nucleophiles is described. The resulting novel chiral derivatives are readily accessible from limonene aziridine in either enantiomeric form in 35-94'% yield. (c) 2005 Elsevier Ltd. All rights reserved.
• Scaleable Syntheses of Isomeric Limonene Aziridines from the Commercially Available Mixture of <i>cis</i>- and <i>trans</i>-Limonene Oxides
  作者：Michael V. Voronkov、Alexander V. Gontcharov、Ramanaiah C. Kanamarlapudi、Paul F. Richardson、Zhi-Min Wang

  DOI：10.1021/op0498464

  日期：2005.3.1

  A short and efficient route to both isomers of limonene aziridine is described. The process is amenable to scale-up and allows easy access to multigram quantities of these highly useful chiral building blocks.
• A convenient synthesis of new diamine, amino alcohol and aminophosphines chiral auxiliaries based on limonene oxide
  作者：Cristina Cimarelli、Davide Fratoni、Gianni Palmieri

  DOI：10.1016/j.tetasy.2009.08.012

  日期：2009.10

  A strategy for the synthesis of new chiral auxiliaries based upon vicinal diamines, amino alcohols and aminophosphines, obtained from limonene oxide, has been developed. The methodology allows the preparation of (1R,2R,4S)-1-methyl-4-(prop-1-en-2-yl)cyclohexane-1,2-diamine starting from a commercially available mixture of cis/trans (4S)-(-)-limonene oxides, through a stereoconvergent synthetic sequence. The process starts from an inexpensive naturally occurring material, is amenable to scale-up and allows easy access to highly useful enantiopure building blocks and ligands, employed in asymmetric catalysis. (C) 2009 Elsevier Ltd. All rights reserved.