2-(3-oxocyclohex-1-enyl)acetic acid | 100378-61-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(3-oxocyclohex-1-enyl)acetic acid
• 英文别名: (3-oxo-cyclohex-1-enyl)-acetic acid；(3-Oxo-cyclohex-1-enyl)-essigsaeure；3-Carboxymethylcyclohexenone；2-(3-oxocyclohexen-1-yl)acetic acid
• CAS: 100378-61-8
• 化学式: C₈H₁₀O₃
• 分子量: 154.166
• InChiKey: ZRHKAWFGGSBCKU-UHFFFAOYSA-N

物化性质

• 沸点：
  334.2±31.0 °C(Predicted)
• 密度：
  1.219±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(3-oxocyclohex-1-enyl)acetic acid 生成 3-甲基-2-环己烯-1-酮
  参考文献：
  名称：

  Grewe et al., Chemische Berichte, 1956, vol. 89, p. 600,608

  摘要：

  DOI：
• 作为产物：
  描述：

  ethyl (3-hydroxy-1-cyclohexenyl)ethanoate 在 C₉H₁₈NO*H⁽¹⁺⁾*BF₄^(1-) 、 水 、 sodium hydroxide 作用下， 以 乙醇 、 乙腈 为溶剂， 反应 6.0h， 生成 2-(3-oxocyclohex-1-enyl)acetic acid
  参考文献：
  名称：

  Model Studies To Access the [6,7,5,5]-Core of Ineleganolide Using Tandem Translactonization–Cope or Cyclopropanation–Cope Rearrangements as Key Steps

  摘要：

  Recently, we reported a convergent cyclopropanation-Cope approach to the core of ineleganolide, which was the first disclosed synthesis of the core of the norditerpene natural product ineleganolide. In this complementary work, a model system for the core of ineleganolide has been prepared through a series of tandem cyclo-propanation-Cope and translactonization-Cope rearrangements. Work with this model system has enriched our understanding of the cyclopropanation-Cope rearrangement sequence. Additionally, research into this model system has driven the development of tandem translactonization-Cope rearrangements.

  DOI：

  10.1021/acs.joc.7b02030

文献信息

• Grewe et al., Chemische Berichte, 1956, vol. 89, p. 600,608
  作者：Grewe et al.

  DOI：——

  日期：——
• Model Studies To Access the [6,7,5,5]-Core of Ineleganolide Using Tandem Translactonization–Cope or Cyclopropanation–Cope Rearrangements as Key Steps
  作者：Jennifer L. Roizen、Amanda C. Jones、Russell C. Smith、Scott C. Virgil、Brian M. Stoltz

  DOI：10.1021/acs.joc.7b02030

  日期：2017.12.15

  Recently, we reported a convergent cyclopropanation-Cope approach to the core of ineleganolide, which was the first disclosed synthesis of the core of the norditerpene natural product ineleganolide. In this complementary work, a model system for the core of ineleganolide has been prepared through a series of tandem cyclo-propanation-Cope and translactonization-Cope rearrangements. Work with this model system has enriched our understanding of the cyclopropanation-Cope rearrangement sequence. Additionally, research into this model system has driven the development of tandem translactonization-Cope rearrangements.