[(1S,2R)-2-(2-Ethoxy-ethoxy)-3,3-dimethyl-cyclobutyl]-acetonitrile | 864915-09-3

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: [(1S,2R)-2-(2-Ethoxy-ethoxy)-3,3-dimethyl-cyclobutyl]-acetonitrile
• 英文别名: 2-[(1S,2R)-2-(2-ethoxyethoxy)-3,3-dimethylcyclobutyl]acetonitrile
• CAS: 864915-09-3
• 化学式: C₁₂H₂₁NO₂
• 分子量: 211.304
• InChiKey: ZFRREMDPQOGOIW-GHMZBOCLSA-N

物化性质

• 沸点：
  304.1±12.0 °C(Predicted)
• 密度：
  0.97±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  42.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  [(1S,2R)-2-(2-Ethoxy-ethoxy)-3,3-dimethyl-cyclobutyl]-acetonitrile 在 盐酸 、 sodium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 生成 (1R,4S,5S)-4-[(E)-(1S,2S)-6-(tert-Butyl-diphenyl-silanyloxy)-1-hydroxy-2-methoxy-4-methyl-hex-3-enyl]-7,7-dimethyl-2-oxa-bicyclo[3.2.0]heptan-3-one
  参考文献：
  名称：

  Synthetic studies of pestalotiopsin A: asymmetric synthesis of the 2-oxabicyclo[3.2.0]heptane substructure

  摘要：

  A functionalized 2-oxabicyclo [3.2.0]heptan-3-one derivative, possessing all the skeletal carbons of pestalotiopsin A, has been synthesized. For the preparation of intermediary cyclobutane derivatives in enantioenriched form, the Lewis acid-catalyzed [2+2] cycloaddition of N-propiolated Oppoizer's camphorsultam with dimethylketene bis(trimethylsilyl) acetal followed by a stereo-selective 1,4-hydride addition/protonation, has been developed. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.06.133
• 作为产物：
  描述：

  (1R,4S)-4-[(tert-butyldiphenylsilyloxy)methyl]-2,2-dimethylcyclobutan-1-ol 在 4-二甲氨基吡啶 、 四丁基氟化铵 、 4-甲基苯磺酸吡啶 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 二甲基亚砜 为溶剂， 生成 [(1S,2R)-2-(2-Ethoxy-ethoxy)-3,3-dimethyl-cyclobutyl]-acetonitrile
  参考文献：
  名称：

  Synthetic studies of pestalotiopsin A: asymmetric synthesis of the 2-oxabicyclo[3.2.0]heptane substructure

  摘要：

  A functionalized 2-oxabicyclo [3.2.0]heptan-3-one derivative, possessing all the skeletal carbons of pestalotiopsin A, has been synthesized. For the preparation of intermediary cyclobutane derivatives in enantioenriched form, the Lewis acid-catalyzed [2+2] cycloaddition of N-propiolated Oppoizer's camphorsultam with dimethylketene bis(trimethylsilyl) acetal followed by a stereo-selective 1,4-hydride addition/protonation, has been developed. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.06.133

文献信息

• Synthetic studies of pestalotiopsin A: asymmetric synthesis of the 2-oxabicyclo[3.2.0]heptane substructure
  作者：Ken-ichi Takao、Hiroshi Saegusa、Tomohiro Tsujita、Takenori Washizawa、Kin-ichi Tadano

  DOI：10.1016/j.tetlet.2005.06.133

  日期：2005.8

  A functionalized 2-oxabicyclo [3.2.0]heptan-3-one derivative, possessing all the skeletal carbons of pestalotiopsin A, has been synthesized. For the preparation of intermediary cyclobutane derivatives in enantioenriched form, the Lewis acid-catalyzed [2+2] cycloaddition of N-propiolated Oppoizer's camphorsultam with dimethylketene bis(trimethylsilyl) acetal followed by a stereo-selective 1,4-hydride addition/protonation, has been developed. (c) 2005 Elsevier Ltd. All rights reserved.