3-(bromomethyl)-2,4-dimethylcyclopent-2-enone | 1202851-48-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-(bromomethyl)-2,4-dimethylcyclopent-2-enone
• 英文别名: 3-(bromomethyl)-2,4-dimethylcyclopent-2-en-1-one
• CAS: 1202851-48-6
• 化学式: C₈H₁₁BrO
• 分子量: 203.079
• InChiKey: RNVRDWBSSSRYRI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 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：

  在 溴化钛(IV) 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 3-(bromomethyl)-2,4-dimethylcyclopent-2-enone 、 trans-5-bromo-2,3,4-trimethylcyclopent-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