trans-1-Phenyl-3-ethoxycarbonyl-2.2-dicyan-cyclopropan | 927176-41-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: trans-1-Phenyl-3-ethoxycarbonyl-2.2-dicyan-cyclopropan
• 英文别名: ethyl (1S,3R)-2,2-dicyano-3-phenylcyclopropane-1-carboxylate
• CAS: 927176-41-8
• 化学式: C₁₄H₁₂N₂O₂
• 分子量: 240.261
• InChiKey: QLZFLGIJZASHFR-NWDGAFQWSA-N

物化性质

• 沸点：
  433.1±45.0 °C(Predicted)
• 密度：
  1.23±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  73.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  、 苄烯丙二腈 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以78%的产率得到trans-1-Phenyl-3-ethoxycarbonyl-2.2-dicyan-cyclopropan
  参考文献：
  名称：

  Enantioselective cyclopropanation reaction using a conformationally fixed pyridinium ylide through a cation–π interaction

  摘要：

  Using a chiral pyridinium ylide with a fixed conformation through a cation-pi interaction performs enantioselective cyclo-propanation of electron-deficient olefins. H-1 NMR, X-ray structural analysis and DFT calculations elucidated the self-complexation and the face-to-face arrangement between the pyridinium and the phenyl rings. The absolute configuration of the product was determined after conversion into a bicyclic cyclopropane derivative. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.11.142

文献信息

• Enantioselective Cyclopropanation Reactions with Planar-Chiral Pyridinium Ylides: A Substituent Effect and a Remote Steric Effect
  作者：Nobuhiro Kanomata、Ryo Sakaguchi、Kazuki Sekine、Satomi Yamashita、Hiroko Tanaka

  DOI：10.1002/adsc.201000079

  日期：2010.11.22

  Novel planar-chiral pyridinium ylides were designed, and generated in situ from the corresponding pyridinium salts with triethylamine. Ylides with a common parapyridinophane skeleton reacted efficiently with electron-deficient dicyanoalkenes, or malononitriles, to produce optically active cyclopropane derivatives with high enantioselectivity (up to 99% ee). Remote steric effects were observed on the

  设计了新颖的平面手性吡啶鎓叶立德，并从相应的吡啶鎓盐与三乙胺就地生成。具有常见的对吡啶并吡啶骨架的叶立德与缺电子的二氰基烯烃或丙二腈有效反应，生成具有高对映选择性（最高ee达99％）的旋光性环丙烷衍生物。观察到对映体选择性的空间位阻效应，其中吡啶并吡啶烷核的R 2基团导致产物的ee值更高。密度泛函理论（DFT）的计算与我们的实验结果非常吻合：大力推动的过渡态产生了主要的立体异构体，即反式-环丙烷产品。
• Enantioselective cyclopropanation reaction using a conformationally fixed pyridinium ylide through a cation–π interaction
  作者：Shinji Yamada、Jun Yamamoto、Emiko Ohta

  DOI：10.1016/j.tetlet.2006.11.142

  日期：2007.1

  Using a chiral pyridinium ylide with a fixed conformation through a cation-pi interaction performs enantioselective cyclo-propanation of electron-deficient olefins. H-1 NMR, X-ray structural analysis and DFT calculations elucidated the self-complexation and the face-to-face arrangement between the pyridinium and the phenyl rings. The absolute configuration of the product was determined after conversion into a bicyclic cyclopropane derivative. (c) 2006 Elsevier Ltd. All rights reserved.