1-(4-chlorobenzoyl)-2-methylenecyclopentanecarboxylic acid methyl ester | 1403993-83-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(4-chlorobenzoyl)-2-methylenecyclopentanecarboxylic acid methyl ester
• 英文别名: Cyclopentanecarboxylic acid, 1-(4-chlorobenzoyl)-2-methylene-, methyl ester；methyl 1-(4-chlorobenzoyl)-2-methylidenecyclopentane-1-carboxylate
• CAS: 1403993-83-8
• 化学式: C₁₅H₁₅ClO₃
• 分子量: 278.735
• InChiKey: DIHBKHFLNDBNNF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.42
• 重原子数：
  19.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  43.37
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  methyl 2-(4-chlorobenzoyl)hept-6-ynoate 在 3,5-bis(pentafluorosulfanyl)phenylboronic acid 作用下， 以 甲苯 为溶剂， 反应 72.0h， 以75%的产率得到1-(4-chlorobenzoyl)-2-methylenecyclopentanecarboxylic acid methyl ester
  参考文献：
  名称：

  3,5-Bis(pentafluorosulfanyl)phenylboronic acid: A new organocatalyst for Conia-ene carbocyclization of 1,3-dicarbonyl compounds having terminal alkynes

  摘要：

  3,5-Bis(pentafluorosulfanyl)phenylboronic acid 1 was introduced as an efficient organocatalyst for Conia-ene carbocyclization of 1,3-dicarbonyl compounds having terminal alkynes. A variety of 2-alkynic 1,3-dicarbonyl compounds were smoothly converted to ene-carbocyclization products in moderate to excellent yields. Compared with the reported catalyst, 3-nitro phenylboronic acid, catalyst 1 is slightly better in a non-polar solvent such as toluene and Solkane(R) 365mfc (1,1,1,3,3-pentafluorobutane). These results indicate that the SF5 function can be a lipophilic and sterically demanding alternative to the NO2 group in catalyst design. (C) 2012 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2012.06.007