2,2-Dichloro-3,3-diethylcyclobutanone | 215957-58-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,2-Dichloro-3,3-diethylcyclobutanone
• 英文别名: 2,2-Dichloro-3,3-diethylcyclobutan-1-one
• CAS: 215957-58-7
• 化学式: C₈H₁₂Cl₂O
• 分子量: 195.089
• InChiKey: QAQAFPUZVGSCPK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2,2-Dichloro-3,3-diethylcyclobutanone 在 bis(1,5-cyclooctadiene)nickel (0) 、 三环己基膦 溶剂黄146 、 锌 作用下， 以 甲苯 为溶剂， 反应 3.0h， 生成 5,5-diphenyl-2,3-dipropyl-2-cyclohexenone
  参考文献：
  名称：

  Two-carbon ring expansion of cyclobutanone skeletons by nickel-catalyzed intermolecular alkyne insertion

  摘要：

  The reaction of cyclobutanone with an alkyne in the presence of a nickel(0) catalyst formally achieves intermolecular alkyne insertion between the carbonyl carbon and the a-carbon of a cyclobutanone, providing a six-membered carbocyclic skeleton. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.03.118
• 作为产物：
  描述：

  3-戊酮 在 sodium hydride 、 锌 作用下， 以 乙醚 、 二甲基亚砜 为溶剂， 反应 3.0h， 生成 2,2-Dichloro-3,3-diethylcyclobutanone
  参考文献：
  名称：

  Adler, Roger W.; Allen, Paul R.; Anderson, Kevin R., Journal of the Chemical Society. Perkin transactions II, 1998, # 10, p. 2083 - 2108

  摘要：

  DOI：

文献信息

• Palladium-Catalyzed Diastereo- and Enantioselective Wagner−Meerwein Shift: Control of Absolute Stereochemistry in the C−C Bond Migration Event
  作者：Barry M. Trost、Jia Xie

  DOI：10.1021/ja7111299

  日期：2008.5.1

  Inducing absolute stereochemistry in Wagner-Meerwein shifts was examined in a ring expansion protocol. Initiated by generation of a pi-allylpalladium intermediate by hydropalladation of allenes, the ring expansion of allenylcyclobutanol substrates proceeded with excellent diastereo- and enantioselectivities. The results demonstrate that, during the C-C bond migration process, our chiral catalysts can control the stereochemistry of both the pi-allylpalladium intermediate and the corresponding migration bond. Moreover, the stereochemical outcome of the reaction can be rationalized very well with the working model of the chiral catalyst. The method provides an efficient way to synthesize highly substituted cyclopentanones with an alpha-chiral O-tertiary center which has various synthetic applications.
• Substitution of chlorocyclobutanones with xanthate salts. The remarkable effect of added base
  作者：Rama Heng、Béatrice Quiclet-Sire、Samir Z. Zard

  DOI：10.1016/j.tetlet.2009.03.133

  日期：2009.7

  The substitution reaction of chlorocyclobutanones with dithiocarbonates (xanthates) is greatly accelerated by the addition of a mild base such as DABCO or DBU. (C) 2009 Elsevier Ltd. All rights reserved.
• Two-carbon ring expansion of cyclobutanone skeletons by nickel-catalyzed intermolecular alkyne insertion
  作者：Masahiro Murakami、Shinji Ashida、Takanori Matsuda

  DOI：10.1016/j.tet.2006.03.118

  日期：2006.8

  The reaction of cyclobutanone with an alkyne in the presence of a nickel(0) catalyst formally achieves intermolecular alkyne insertion between the carbonyl carbon and the a-carbon of a cyclobutanone, providing a six-membered carbocyclic skeleton. (c) 2006 Elsevier Ltd. All rights reserved.
• Adler, Roger W.; Allen, Paul R.; Anderson, Kevin R., Journal of the Chemical Society. Perkin transactions II, 1998, # 10, p. 2083 - 2108
  作者：Adler, Roger W.、Allen, Paul R.、Anderson, Kevin R.、Butts, Craig P.、Khosravi, Ezat、et al.

  DOI：——

  日期：——