2,2-dimethoxycarbonyl-1-cyano-1-phenylethane | 38264-38-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 2,2-dimethoxycarbonyl-1-cyano-1-phenylethane
• 英文别名: (cyano-phenyl-methyl)-malonic acid dimethyl ester；(Cyan-phenyl-methyl)-malonsaeure-dimethylester；Dimethyl-β-cyanobenzylmalonate；Dimethyl 2-[cyano(phenyl)methyl]propanedioate
• CAS: 38264-38-9
• 化学式: C₁₃H₁₃NO₄
• 分子量: 247.251
• InChiKey: AYAOGECTPXNKJY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  76.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  亚苄基丙二酸二甲酯 在 甲醇 、 potassium cyanide 作用下， 生成 2,2-dimethoxycarbonyl-1-cyano-1-phenylethane
  参考文献：
  名称：

  On 1,2- and 1,4-Addition. I. The 1,4-Addition of Potassium Isocyanide¹

  摘要：

  DOI：

  10.1021/ja01283a043

文献信息

• The study of reaction mechanism for the transformation of nitronate into nitrile by phosphorus trichloride
  作者：Zhijay Tu、Yaochung Jang、Chunchi Lin、Ju-Tsung Liu、Jianming Hsu、M.N.V. Sastry、Ching-Fa Yao

  DOI：10.1016/j.tet.2005.08.041

  日期：2005.10

  investigated under different conditions. With different anions of malonates containing dipolarphiles, cyclic compounds were obtained as major products indicating nitrile oxides were generated during the reaction. Based on the results, compared to that of the one reported in literature, a plausible mechanism involving nitrile oxide intermediate was proposed.

  使用β-硝基苯乙烯和丙二酸二甲酯的阴离子在THF中于0°C生成硝酸盐。随后在THF或吡啶中存在/不存在DMAP的情况下用PCl 3处理，得到硝基烷，氯肟和腈。在不同条件下研究了吡啶，THF和THF-吡啶共溶剂作为溶剂。用含有双极性亲电子的丙二酸根的不同阴离子，获得了环状化合物作为主要产物，表明在反应过程中产生了腈氧化物。根据这些结果，与文献报道的结果相比，提出了一种涉及一氧化氮中间体的合理机理。
• Asymmetric Cyanation of Activated Olefins with Ethyl Cyanoformate Catalyzed by a Modular Titanium Catalyst
  作者：Jun Wang、Wei Li、Yanling Liu、Yangyang Chu、Lili Lin、Xiaohua Liu、Xiaoming Feng

  DOI：10.1021/ol100169r

  日期：2010.3.19

  Asymmetric cyanation of a class of easily available olefins with a favorable cyanide source ethyl cyanoformate (CNCOOEt) was realized by an interesting modular catalyst. High yields and ee values were obtained for a range of substrates under solvent-free and mild reaction conditions. The products obtained could be easily transformed to the enantioenriched useful intermediates 5, 6, and pharmaceutically important gamma-aminobutyric acid 7.