2-methyl-4-bromocyclopent-2-en-1-one | 147297-98-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-methyl-4-bromocyclopent-2-en-1-one
• 英文别名: 4-bromo-2-methylcyclopent-2-enone；4-bromo-2-methyl-2-cyclopenten-1-one；4-Bromo-2-methylcyclopent-2-en-1-one
• CAS: 147297-98-1
• 化学式: C₆H₇BrO
• 分子量: 175.025
• InChiKey: OLIJKLUJDASWHH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  8
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 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-methyl-4-bromocyclopent-2-en-1-one 在 水 作用下， 以 1,4-二氧六环 为溶剂， 反应 3.0h， 以65%的产率得到4-羟基-2-甲基环戊-2-烯-1-酮
  参考文献：
  名称：

  A Facile, Efficient Synthesis of 2-substituted-4-Hydroxy- 2-cyclopenten-1-ones

  摘要：

  描述了一种将2取代的4-溴-2-环戊烯-1-酮转化为标题化合物及其对应的4-甲氧基衍生物的简单程序。

  DOI：

  10.1055/s-1986-31779
• 作为产物：
  描述：

  (±)-4-hydroxy-5-methylcyclopent-2-en-1-one 在 三乙胺 、 lithium bromide 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 3.0h， 生成 2-methyl-4-bromocyclopent-2-en-1-one
  参考文献：
  名称：

  Pseudocine substitution of 4-(mesyloxy)-2-cyclopentenones: an efficient route to 2,4-disubstituted 2-cyclopentenones

  摘要：

  Readily available mesylates 1a-d were found to undergo a novel substitution reaction. In the presence of a variety of nucleophiles, 1a-d underwent a net substitution in which the nucleophile was introduced vicinally (C-3) to the departing mesylate (C-4) and the double bond migrated to C-4/C-5. Lithium bromide, thiophenol, benzylamine, sodium azide, and the potassium salt of dimethyl malonate all led to substitution products in good yield. The reaction is thought to proceed by way of initial conjugate addition of the nucleophile, followed by enolate equilibration and beta-elimination of mesylate.

  DOI：

  10.1021/jo00061a010

文献信息

• <i>N</i>-Phthaloylglycine-Derived Strigol Analogues. Influence of the D-Ring on Seed Germination Activity of the Parasitic Weeds <i>Striga hermonthica</i> and <i>Orobanche crenata</i>
  作者：Jan Willem J. F. Thuring、Harry H. Bitter、Margreet M. de Kok、Gérard H. L. Nefkens、Annemiek M. D. A. van Riel、Binne Zwanenburg

  DOI：10.1021/jf9604652

  日期：1997.6.1

  Several strigol analogues with modifications in the D-ring were synthesized and assayed for germination stimulatory activity of seeds of Striga hermonthica and Orobanche crenata. All of these D-ring analogues are derived from N-phthaloylglycine as the common ABC-fragment. It was concluded that the correct structure of the 2(5H)-furanone D-ring is essential to retain full biological activity.
• Kirchner, Karl; Mereiter, Kurt; Umfahrer, Arno, Organometallics, 1994, vol. 13, # 5, p. 1886 - 1892
  作者：Kirchner, Karl、Mereiter, Kurt、Umfahrer, Arno、Schmid, Roland

  DOI：——

  日期：——
• A Facile, Efficient Synthesis of 2-substituted-4-Hydroxy- 2-cyclopenten-1-ones
  作者：P. G. Baraldi、G. P. Pollini、D. Simoni、V. Zanirato、A. Barco、S. Benetti

  DOI：10.1055/s-1986-31779

  日期：——

  A simple procedure for the transformation of 2-substituted 4-bromo-2-cyclopenten-1-ones into the title compounds as well as into the corresponding 4-methoxy derivatives is described.

  描述了一种将2取代的4-溴-2-环戊烯-1-酮转化为标题化合物及其对应的4-甲氧基衍生物的简单程序。
• Pseudocine substitution of 4-(mesyloxy)-2-cyclopentenones: an efficient route to 2,4-disubstituted 2-cyclopentenones
  作者：F. G. West、Gamini U. Gunawardena

  DOI：10.1021/jo00061a010

  日期：1993.4

  Readily available mesylates 1a-d were found to undergo a novel substitution reaction. In the presence of a variety of nucleophiles, 1a-d underwent a net substitution in which the nucleophile was introduced vicinally (C-3) to the departing mesylate (C-4) and the double bond migrated to C-4/C-5. Lithium bromide, thiophenol, benzylamine, sodium azide, and the potassium salt of dimethyl malonate all led to substitution products in good yield. The reaction is thought to proceed by way of initial conjugate addition of the nucleophile, followed by enolate equilibration and beta-elimination of mesylate.