(1S,3S)-2,2-dimethyl-3-(2-methylprop-1-en-1-yl)cyclopropanecarboxamide | 494846-49-0

• 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: (1S,3S)-2,2-dimethyl-3-(2-methylprop-1-en-1-yl)cyclopropanecarboxamide
• 英文别名: (-)-trans-(1S,3S)-2,2-dimethyl-3-(2',2'-dimethylvinyl)cyclopropanecarboxamide；(-)-trans-chrysanthemic acid amide；(-)-trans-chrysanthemumic acid amide；(-)-trans-Chrysanthemumsaeure-amid；(1S,3S)-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropane-1-carboxamide
• CAS: 494846-49-0
• 化学式: C₁₀H₁₇NO
• 分子量: 167.251
• InChiKey: GFXSLQNAAAQQSB-JGVFFNPUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  43.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (1S,3S)-2,2-dimethyl-3-(2-methylprop-1-en-1-yl)cyclopropanecarboxamide 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 生成 trans-Chrysanthemylamin
  参考文献：
  名称：

  Chemoenzymatic synthesis of enantiopure geminally dimethylated cyclopropane-based C2- and pseudo-C2-symmetric diamines

  摘要：

  Enantiopure (-)-(1S,3S)-2,2-dimethyl-3-(2-methylprop-l-enyl)cyclopropanecarboxamide 2 and (+)-(1R,3R)-2,2-dimethyl-3(2-methylprop-l-enyl)cyclopropanecarboxylic acid 3 were easily obtained from a multigram scale biotransformation of racemic amide or nitrile in the presence of Rhodococcus erythropolis AJ270 whole cell catalyst under very mild conditions. Coupled with efficient and convenient chemical manipulations, comprising mainly of the Curtius rearrangement, oxidation, and reduction reactions, chiral C-2-symmetric (1S,2S)-3,3-dimethylcyclopropane-1,2-diamine 6 and ((1R,3R)-3-(aminomethyl)-2,2-dimethylcyclopropyl)methanamine 8 and pseudo-C-2-symmetric (1S,3S)-3-(aminomethyl)-2,2-dimethylcyclopropanamine 11 were prepared. These were also transformed into the corresponding chiral salen derivatives 12, 13, and 14, respectively, in almost quantitative yields. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.10.030
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 生成 (1S,3S)-2,2-dimethyl-3-(2-methylprop-1-en-1-yl)cyclopropanecarboxamide
  参考文献：
  名称：

  74.合成除虫菊酯的实验。第一部分菊花一元羧酸的合成

  摘要：

  DOI：

  10.1039/jr9450000283

文献信息

• Nitrile Biotransformation for Highly Enantioselective Synthesis of 3-Substituted 2,2-Dimethylcyclopropanecarboxylic Acids and Amides
  作者：Mei-Xiang Wang、Guo-Qiang Feng

  DOI：10.1021/jo026490q

  日期：2003.1.1

  2-dimethylcyclopropanecarbonitriles appeared inert toward the biocatalyst, a number of racemic trans-isomers efficiently underwent a highly enantioselective hydrolysis to produce (+)-(1R,3R)-3-aryl-2,2-dimethylcyclopropanecarboxylic acids and (-)-(1S,3S)-3-aryl-2,2-dimethylcyclopropanecarboxamides in high yields with excellent enantiomeric excesses in most cases. The overall enantioselectivity of the

  使用含有腈水合酶/酰胺酶的红球菌研究了不同构型的2,2-二甲基-3-取代的环丙烷甲腈的生物转化。AJ270全细胞催化剂在非常温和的条件下。尽管所有的cis-3-芳基-2,2-二甲基环丙烷甲腈对生物催化剂均呈惰性，但许多外消旋反式异构体均经过高度对映选择性水解，生成（+）-（1R，3R）-3-芳基-大多数情况下，以高收率得到2,2-二甲基环丙烷羧酸和（-）-（1S，3S）-3-芳基-2,2-二甲基环丙烷甲酰胺。腈类生物转化的整体对映选择性源于1R-对映选择性腈水合酶和酰胺酶的联合作用，后者是主要因素。从空间和电子效应的角度讨论了底物对反应效率和对映选择性的影响。与化学转化相结合，腈的生物转化提供了两种对映体形式的光学纯的双键取代的光学纯的双甲基取代的环丙烷羧酸和酰胺（包括菊酸）的合成。
• 74. Experiments on the synthesis of the pyrethrins. Part I. Synthesis of chrysanthemum monocarboxylic acid
  作者：I. G. M. Campbell、Stanley H. Harper

  DOI：10.1039/jr9450000283

  日期：——
• Chemoenzymatic synthesis of enantiopure geminally dimethylated cyclopropane-based C2- and pseudo-C2-symmetric diamines
  作者：Guo-Qiang Feng、De-Xian Wang、Qi-Yu Zheng、Mei-Xiang Wang

  DOI：10.1016/j.tetasy.2006.10.030

  日期：2006.10

  Enantiopure (-)-(1S,3S)-2,2-dimethyl-3-(2-methylprop-l-enyl)cyclopropanecarboxamide 2 and (+)-(1R,3R)-2,2-dimethyl-3(2-methylprop-l-enyl)cyclopropanecarboxylic acid 3 were easily obtained from a multigram scale biotransformation of racemic amide or nitrile in the presence of Rhodococcus erythropolis AJ270 whole cell catalyst under very mild conditions. Coupled with efficient and convenient chemical manipulations, comprising mainly of the Curtius rearrangement, oxidation, and reduction reactions, chiral C-2-symmetric (1S,2S)-3,3-dimethylcyclopropane-1,2-diamine 6 and ((1R,3R)-3-(aminomethyl)-2,2-dimethylcyclopropyl)methanamine 8 and pseudo-C-2-symmetric (1S,3S)-3-(aminomethyl)-2,2-dimethylcyclopropanamine 11 were prepared. These were also transformed into the corresponding chiral salen derivatives 12, 13, and 14, respectively, in almost quantitative yields. (c) 2006 Elsevier Ltd. All rights reserved.