1-(2-methylbenzoyl)-2-methylenecyclopentanecarboxylic acid methyl ester | 1224963-61-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(2-methylbenzoyl)-2-methylenecyclopentanecarboxylic acid methyl ester
• 英文别名: Methyl 1-(2-methylbenzoyl)-2-methylidenecyclopentane-1-carboxylate；methyl 1-(2-methylbenzoyl)-2-methylidenecyclopentane-1-carboxylate
• CAS: 1224963-61-4
• 化学式: C₁₆H₁₈O₃
• 分子量: 258.317
• InChiKey: DVTIGZRIVPZGHW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  Methyl 2-(2-methylbenzoyl)hept-6-ynoate 在 3-硝基苯硼酸 作用下， 以 甲苯 为溶剂， 反应 30.0h， 以76%的产率得到1-(2-methylbenzoyl)-2-methylenecyclopentanecarboxylic acid methyl ester
  参考文献：
  名称：

  硼酸催化炔属二羰基化合物的烯碳环化。

  摘要：

  描述了在3-硝基苯硼酸催化下，带有悬垂的末端炔基取代基的1，3-二羰基化合物的有效烯碳环化的发现和发展。该反应是有效的，易于进行的并且通常适用于多种酮酸酯底物。

  DOI：

  10.1039/b924899d

文献信息

• Boronic acid catalyzed ene carbocyclization of acetylenic dicarbonyl compounds
  作者：Meiling Li、Ting Yang、Darren J. Dixon

  DOI：10.1039/b924899d

  日期：——

  The discovery and development of an efficient ene carbocyclization of 1,3-dicarbonyl compounds bearing pendent terminal alkyne substituents under 3-nitrobenzeneboronic acid catalysis is described. The reaction is efficient, easy to perform and general to a wide range of ketoester substrates.

  描述了在3-硝基苯硼酸催化下，带有悬垂的末端炔基取代基的1，3-二羰基化合物的有效烯碳环化的发现和发展。该反应是有效的，易于进行的并且通常适用于多种酮酸酯底物。
• 3,5-Bis(pentafluorosulfanyl)phenylboronic acid: A new organocatalyst for Conia-ene carbocyclization of 1,3-dicarbonyl compounds having terminal alkynes
  作者：Yu-Dong Yang、Xu Lu、Etsuko Tokunaga、Norio Shibata

  DOI：10.1016/j.jfluchem.2012.06.007

  日期：2012.11

  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.