Cyclopentanediacetic acid chloride | 105743-63-3

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 酰卤
• 英文名称: Cyclopentanediacetic acid chloride
• 英文别名: 2,2'-(Cyclopentane-1,1-diyl)diacetyl chloride；2-[1-(2-chloro-2-oxoethyl)cyclopentyl]acetyl chloride
• CAS: 105743-63-3
• 化学式: C₉H₁₂Cl₂O₂
• 分子量: 223.099
• InChiKey: MDDMRDMVEYLHAK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  重氮甲烷 、 Cyclopentanediacetic acid chloride 以 乙醚 为溶剂， 以47%的产率得到1,1'-Cyclopentylidenebis(3-diazo-2-propanone)
  参考文献：
  名称：

  Intramolecular Cooperative Reactions of 1,2-Bis(diazoketone)s. The First Syntheses of trans-Hydro-1H-2-inden-1-ones

  摘要：

  The intramolecular cooperative reactions of 1,2-bis(diazoketone)s initiated by the Wolff rearrangement of alpha-diazoketones have been investigated. Under thermal conditions, 1,2-bis(diazoketone)s are efficiently transformed into 2-cyclopenten-1-one derivatives with complete stereospecificity. Thus, a most extraordinary result is reported, that trans-hydro-2-inden-1-ones (1-3) were synthesized for the first time from trans-1,2-bis(diazoketone)s (5, 11, and 12), respectively. The unprecedented trans-hydroindenone structure was confirmed by X-ray analysis of 3 as well as H-1 NMR analysis and was supported by ab initio molecular orbital calculations. The same reactions were also carried out under photochemical conditions and were applied to 1,3-bis(diazoketone)s, giving 2-cyclohexen-1-one derivatives.

  DOI：

  10.1021/jo00113a030
• 作为产物：
  描述：

  1,1-环戊烷二乙酸 在 五氯化磷 作用下， 以91%的产率得到Cyclopentanediacetic acid chloride
  参考文献：
  名称：

  Intramolecular Cooperative Reactions of 1,2-Bis(diazoketone)s. The First Syntheses of trans-Hydro-1H-2-inden-1-ones

  摘要：

  The intramolecular cooperative reactions of 1,2-bis(diazoketone)s initiated by the Wolff rearrangement of alpha-diazoketones have been investigated. Under thermal conditions, 1,2-bis(diazoketone)s are efficiently transformed into 2-cyclopenten-1-one derivatives with complete stereospecificity. Thus, a most extraordinary result is reported, that trans-hydro-2-inden-1-ones (1-3) were synthesized for the first time from trans-1,2-bis(diazoketone)s (5, 11, and 12), respectively. The unprecedented trans-hydroindenone structure was confirmed by X-ray analysis of 3 as well as H-1 NMR analysis and was supported by ab initio molecular orbital calculations. The same reactions were also carried out under photochemical conditions and were applied to 1,3-bis(diazoketone)s, giving 2-cyclohexen-1-one derivatives.

  DOI：

  10.1021/jo00113a030

文献信息

• US5990124A
  申请人：——

  公开号：US5990124A

  公开（公告）日：1999-11-23
• US6274623B1
  申请人：——

  公开号：US6274623B1

  公开（公告）日：2001-08-14
• US6274757B1
  申请人：——

  公开号：US6274757B1

  公开（公告）日：2001-08-14
• US6376510B1
  申请人：——

  公开号：US6376510B1

  公开（公告）日：2002-04-23
• Intramolecular Cooperative Reactions of 1,2-Bis(diazoketone)s. The First Syntheses of trans-Hydro-1H-2-inden-1-ones
  作者：Kazuhiko Nakatani、Kazunori Takada、Sachihiko Isoe

  DOI：10.1021/jo00113a030

  日期：1995.4

  The intramolecular cooperative reactions of 1,2-bis(diazoketone)s initiated by the Wolff rearrangement of alpha-diazoketones have been investigated. Under thermal conditions, 1,2-bis(diazoketone)s are efficiently transformed into 2-cyclopenten-1-one derivatives with complete stereospecificity. Thus, a most extraordinary result is reported, that trans-hydro-2-inden-1-ones (1-3) were synthesized for the first time from trans-1,2-bis(diazoketone)s (5, 11, and 12), respectively. The unprecedented trans-hydroindenone structure was confirmed by X-ray analysis of 3 as well as H-1 NMR analysis and was supported by ab initio molecular orbital calculations. The same reactions were also carried out under photochemical conditions and were applied to 1,3-bis(diazoketone)s, giving 2-cyclohexen-1-one derivatives.