Methyl 3-methyl-3-phenyl-4,4,5,5-tetracyanopentanoate

• 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: Methyl 3-methyl-3-phenyl-4,4,5,5-tetracyanopentanoate
• 英文别名: Methyl 4,4,5,5-tetracyano-3-methyl-3-phenylpentanoate
• 化学式: C₁₇H₁₄N₄O₂
• 分子量: 306.324
• InChiKey: HTNWLIPNDYZAOD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  122
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  1-Methoxy-1-(trimethylsiloxy)-2,2,3,3-tetracyano-4-methyl-4-phenylcyclopentane 在 水 、 silica gel 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 Methyl 3-methyl-3-phenyl-4,4,5,5-tetracyanopentanoate
  参考文献：
  名称：

  Electron Transfer Profile of Cyclopropanone Acetals in the Nonirradiated Reaction with Tetracyanoethylene, Chloranil, and Dicyanodichlorobenzoquinone

  摘要：

  The donor profiles of cyclopropanone acetals 1 and 2 were examined in the reactions with electron accepters (TCNE, DDQ, chloranil, and 1-cyanonaphthalene). With TCNE under nonirradiating conditions, an exclusive 2 + 2 cycloaddition took place stereospecifically with monosubstituted acetals 1a-c but nonstereospecifically with disubstituted acetals 1d,e. With quinones, a ring-opening of the cyclopropane and its coupling with the quinone took place to give the C (cyclopropane)-O (quinone) adduct 9 (with chloranil) or 10 (with DDQ), the latter of which underwent the elimination of a phenol to produce unsaturated esters 5 and 6. In addition, the intervention of the C (cyclopropane)-C (quinone) adduct 14 (with chloranil) or 15 (with DDQ), both as the precursor of 5 and 6, was also postulated. With 1-cyanonaphthalene, under photolysis, the cis/trans isomerization of 1 and 2 occurred. The results provided evidences that cyclopropanone acetals, in general, are prone to function as donors. The mechanism of the reaction with quinones, in particular, was investigated in detail.

  DOI：

  10.1021/jo00103a043