1-(3-Bromo-2-bromomethyl-propyl)-cyclohex-2-enecarboxylic acid methyl ester | 201337-13-5

• 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: 1-(3-Bromo-2-bromomethyl-propyl)-cyclohex-2-enecarboxylic acid methyl ester
• CAS: 201337-13-5
• 化学式: C₁₂H₁₈Br₂O₂
• 分子量: 354.082
• InChiKey: IQMSEKBOGXLGEL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.68
• 重原子数：
  16.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  1-(3-Bromo-2-bromomethyl-propyl)-cyclohex-2-enecarboxylic acid methyl ester 在 偶氮二异丁腈 、 三苯基氢化锡 作用下， 以 苯 为溶剂， 生成 Methyl 1-(2-methylpropyl)cyclohex-2-ene-1-carboxylate 、 (2R,3aS,7aS)-2-Methyl-octahydro-indene-3a-carboxylic acid methyl ester 、 (2S,3aS,7aS)-2-Methyl-octahydro-indene-3a-carboxylic acid methyl ester
  参考文献：
  名称：

  Stereoselection at the Steady State. Group Selective Radical Cyclizations of Substrates Containing Two Radical Precursors and One Radical Acceptor

  摘要：

  The kinetic model for compound stereoselection presented in previous paper is verified experimentally by conducting a series of radical cyclizations of 1-(3-halo-2-(halomethyl)propyl)cycloalk-2-enecarboxylates with tributyltin hydride and measuring the ratios of products. Cyclization rate constants are abstracted from the data by an analysis that minimizes total error, and these rate constants compare favorably with rate constants that we measured directly on the corresponding monohalides. Transition state modeling was used to interpret the initial round of results and to design two new systems, one of which was predicted to cyclize with higher selectivity than the parent and the other of which was predicted to cyclize with reverse selectivity. These substrates bearing 4-tert-butyl groups were synthesized, and the experimental results verified the computational predictions.

  DOI：

  10.1021/ja9724102
• 作为产物：
  描述：

  1-[3-(tert-Butyl-dimethyl-silanyloxy)-2-(tert-butyl-dimethyl-silanyloxymethyl)-propyl]-cyclohex-2-enecarboxylic acid methyl ester 在 triphenylphosphine dibromide 1:1 addition complex 作用下， 生成 1-(3-Bromo-2-bromomethyl-propyl)-cyclohex-2-enecarboxylic acid methyl ester
  参考文献：
  名称：

  Stereoselection at the Steady State. Group Selective Radical Cyclizations of Substrates Containing Two Radical Precursors and One Radical Acceptor

  摘要：

  The kinetic model for compound stereoselection presented in previous paper is verified experimentally by conducting a series of radical cyclizations of 1-(3-halo-2-(halomethyl)propyl)cycloalk-2-enecarboxylates with tributyltin hydride and measuring the ratios of products. Cyclization rate constants are abstracted from the data by an analysis that minimizes total error, and these rate constants compare favorably with rate constants that we measured directly on the corresponding monohalides. Transition state modeling was used to interpret the initial round of results and to design two new systems, one of which was predicted to cyclize with higher selectivity than the parent and the other of which was predicted to cyclize with reverse selectivity. These substrates bearing 4-tert-butyl groups were synthesized, and the experimental results verified the computational predictions.

  DOI：

  10.1021/ja9724102