3-chloro-4-methyl-3-pentyl-4-penten-2-one | 131353-09-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-chloro-4-methyl-3-pentyl-4-penten-2-one
• 英文别名: 3-Chloro-3-prop-1-en-2-yloctan-2-one
• CAS: 131353-09-8
• 化学式: C₁₁H₁₉ClO
• 分子量: 202.724
• InChiKey: PGGIUXAEVSNBHY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  13
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.73
• 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：

  3-chloro-4-methyl-3-pentyl-4-penten-2-one 在 正丁基锂 、 二异丙胺 作用下， 以 六甲基磷酰三胺 、 正己烷 为溶剂， 以68%的产率得到二氢茉莉酮
  参考文献：
  名称：

  Base-induced cyclization of .alpha.-chloro .beta.,.gamma.-unsaturated ketones : facile synthesis of tri- and tetrasubstituted 2-cyclopenten-1-ones

  摘要：

  Base-induced cyclization of fully substituted alpha-chloro beta,gamma-unsaturated ketones results in substituted cyclopentenones. Potassium tert-butoxide, lithium diisopropylamide, sodium hydroxide, and ammonium hydroxide can be used as the base for this process. In the case of ammonium hydroxide, it is proposed that initial formation of an enamine is followed by an intramolecular S(N)2' reaction of the enamine carbon. For all other bases, the reaction most likely proceeds through a ketone enolate. Application of this novel cyclization has been extended to the synthesis of several 2,3-disubstituted, 2,3,5-trisubstituted, and 2,3,5-tetrasubstituted 2-cyclopenten-1-ones.

  DOI：

  10.1021/jo00002a042
• 作为产物：
  描述：

  4-methyl-3-pentyl-pent-3-en-2-one 在 calcium hypochlorite 、 溶剂黄146 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 0.33h， 以81%的产率得到3-chloro-4-methyl-3-pentyl-4-penten-2-one
  参考文献：
  名称：

  Base-induced cyclization of .alpha.-chloro .beta.,.gamma.-unsaturated ketones : facile synthesis of tri- and tetrasubstituted 2-cyclopenten-1-ones

  摘要：

  Base-induced cyclization of fully substituted alpha-chloro beta,gamma-unsaturated ketones results in substituted cyclopentenones. Potassium tert-butoxide, lithium diisopropylamide, sodium hydroxide, and ammonium hydroxide can be used as the base for this process. In the case of ammonium hydroxide, it is proposed that initial formation of an enamine is followed by an intramolecular S(N)2' reaction of the enamine carbon. For all other bases, the reaction most likely proceeds through a ketone enolate. Application of this novel cyclization has been extended to the synthesis of several 2,3-disubstituted, 2,3,5-trisubstituted, and 2,3,5-tetrasubstituted 2-cyclopenten-1-ones.

  DOI：

  10.1021/jo00002a042

文献信息

• MATHEW, JACOB, J. ORG. CHEM., 56,(1991) N, C. 713-716
  作者：MATHEW, JACOB

  DOI：——

  日期：——
• US5026918A
  申请人：——

  公开号：US5026918A

  公开（公告）日：1991-06-25
• Base-induced cyclization of .alpha.-chloro .beta.,.gamma.-unsaturated ketones : facile synthesis of tri- and tetrasubstituted 2-cyclopenten-1-ones
  作者：Jacob Mathew

  DOI：10.1021/jo00002a042

  日期：1991.1

  Base-induced cyclization of fully substituted alpha-chloro beta,gamma-unsaturated ketones results in substituted cyclopentenones. Potassium tert-butoxide, lithium diisopropylamide, sodium hydroxide, and ammonium hydroxide can be used as the base for this process. In the case of ammonium hydroxide, it is proposed that initial formation of an enamine is followed by an intramolecular S(N)2' reaction of the enamine carbon. For all other bases, the reaction most likely proceeds through a ketone enolate. Application of this novel cyclization has been extended to the synthesis of several 2,3-disubstituted, 2,3,5-trisubstituted, and 2,3,5-tetrasubstituted 2-cyclopenten-1-ones.