3-(chloromethyl)-2-methylcyclopent-2-enone | 1202851-66-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-(chloromethyl)-2-methylcyclopent-2-enone
• 英文别名: 3-(Chloromethyl)-2-methylcyclopent-2-en-1-one
• CAS: 1202851-66-8
• 化学式: C₇H₉ClO
• mdl: MFCD19236688
• 分子量: 144.601
• InChiKey: SUPLQQHAGDFVPA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.571
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  4-methylhexa-1,4,5-trien-3-one 在 indium(III) chloride 作用下， 以 二氯甲烷 为溶剂， 以31%的产率得到3-(chloromethyl)-2-methylcyclopent-2-enone
  参考文献：
  名称：

  Formation of halogenated cyclopent-2-enone derivatives by interrupted Nazarov cyclizations

  摘要：

  Allenyl vinyl ketones were exposed to titanium and indium halides in order to carry out Nazarov cyclizations. Whereas Til(4) and InX3 (X = Cl, Br, and I) led to cyclopentenones in which a halogen was trapped highly regioselectively, the reactions mediated by TiBr4 gave mixtures of brominated isomers. When the allenyl vinyl ketones were treated first with Br-2 and then with TiBr4, doubly brominated cyclopentenones resulted, and treatment with I-2 followed by TFA gave cyclopentenones bearing both hydroxyl and iodo groups. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.10.052

文献信息

• Formation of halogenated cyclopent-2-enone derivatives by interrupted Nazarov cyclizations
  作者：Vanessa M. Marx、T. Stanley Cameron、D. Jean Burnell

  DOI：10.1016/j.tetlet.2009.10.052

  日期：2009.12

  Allenyl vinyl ketones were exposed to titanium and indium halides in order to carry out Nazarov cyclizations. Whereas Til(4) and InX3 (X = Cl, Br, and I) led to cyclopentenones in which a halogen was trapped highly regioselectively, the reactions mediated by TiBr4 gave mixtures of brominated isomers. When the allenyl vinyl ketones were treated first with Br-2 and then with TiBr4, doubly brominated cyclopentenones resulted, and treatment with I-2 followed by TFA gave cyclopentenones bearing both hydroxyl and iodo groups. (C) 2009 Elsevier Ltd. All rights reserved.