(2-methylenecyclopentane-1,1-diyl)bis(phenylmethanone) | 1380097-21-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2-methylenecyclopentane-1,1-diyl)bis(phenylmethanone)
• 英文别名: (1-Benzoyl-2-methylidenecyclopentyl)-phenylmethanone
• CAS: 1380097-21-1
• 化学式: C₂₀H₁₈O₂
• 分子量: 290.362
• InChiKey: BHTDGYFHPQVBKK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-(pent-4-ynyl)-1,3-diphenylpropane-1,3-dione 在 iron(III) chloride 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 58.0h， 以58%的产率得到(2-methylenecyclopentane-1,1-diyl)bis(phenylmethanone)
  参考文献：
  名称：

  铁（III）催化的2-炔1,3-二羰基化合物的Conia-Ene环化反应

  摘要：

  廉价，简单，有效的FeCl 3催化的2-炔烃1,3-二羰基化合物的Conia-ene环化具有立体特异性，可以通过5 -exo-dig途径得到（E）异构体中的亚烷基环戊烷。根据底物的结构，也可以进行5 -endo-dig和6 -exo-dig环化。

  DOI：

  10.1021/jo300957q

文献信息

• Iron(III)-Catalyzed Conia–Ene Cyclization of 2-Alkynic 1,3-Dicarbonyl Compounds
  作者：Li Yan Chan、Sunggak Kim、Youngchul Park、Phil Ho Lee

  DOI：10.1021/jo300957q

  日期：2012.6.15

  A cheap, simple, and effective FeCl3-catalyzed Conia–ene cyclization of 2-alkynic 1,3-dicarbonyl compounds was stereospecific to afford alkylidenecyclopentanes in (E)-isomers via the 5-exo-dig pathway. The 5-endo-dig and 6-exo-dig cyclizations were also possible, depending on the structure of the substrates.

  廉价，简单，有效的FeCl 3催化的2-炔烃1,3-二羰基化合物的Conia-ene环化具有立体特异性，可以通过5 -exo-dig途径得到（E）异构体中的亚烷基环戊烷。根据底物的结构，也可以进行5 -endo-dig和6 -exo-dig环化。
• 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.