2-(2'-ethoxycarbonyl)ethyl-γ-butyrolactone | 54069-02-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 2-(2'-ethoxycarbonyl)ethyl-γ-butyrolactone
• 英文别名: ethyl 3-(2-oxotetrahydrofuran-3-yl)propanoate；3-Furanpropanoic acid, tetrahydro-2-oxo-, ethyl ester；ethyl 3-(2-oxooxolan-3-yl)propanoate
• CAS: 54069-02-2
• 化学式: C₉H₁₄O₄
• 分子量: 186.208
• InChiKey: ACBHXIYGKXGGNW-UHFFFAOYSA-N

物化性质

• 沸点：
  303.3±15.0 °C(Predicted)
• 密度：
  1.116±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  一氧化碳 、 6-Hydroxy-4-iodo-hexanoic acid ethyl ester 在 偶氮二异丁腈 、 烯丙基三丁基锡 、 三乙胺 作用下， 以 正己烷 、 乙腈 为溶剂， 80.0 ℃ 、4.56 MPa 条件下， 反应 12.0h， 以84%的产率得到2-(2'-ethoxycarbonyl)ethyl-γ-butyrolactone
  参考文献：
  名称：

  Lactone Synthesis Based on Atom Transfer Carbonylation

  摘要：

  [GRAPHICS]Five- to seven-membered lactones were prepared from omega-hydroxyalkyl iodides and CO by atom transfer carbonylation without the need for transition metal catalysts, The reaction proceeds via a hybrid radical/ionic mechanism in which the intramolecular alcoholysis of an omega-hydroxyacyl iodide, arising from atom transfer carbonylation, leads to the lactone.

  DOI：

  10.1021/ol9913441

文献信息

• Pd/Light-Accelerated Atom-Transfer Carbonylation of Alkyl Iodides: Applications in Multicomponent Coupling Processes Leading to Functionalized Carboxylic Acid Derivatives
  作者：Akira Fusano、Shuhei Sumino、Satoshi Nishitani、Takaya Inouye、Keisuke Morimoto、Takahide Fukuyama、Ilhyong Ryu

  DOI：10.1002/chem.201200752

  日期：2012.7.23

  The atom‐transfer carbonylation reaction of various alkyl iodides thereby leading to carboxylic acid esters was effectively accelerated by the addition of transition‐metal catalysts under photoirradiation conditions. By using a combined Pd/hν reaction system, vicinal C‐functionalization of alkenes was attained in which α‐substituted iodoalkanes, alkenes, carbon monoxide, and alcohols were coupled to

  通过在光辐照条件下添加过渡金属催化剂，可以有效地加速各种烷基碘的原子转移羰基化反应，从而生成羧酸酯。通过使用组合的Pd / hν反应系统，烯烃达到了邻位的C-官能化，其中α-取代的碘代烷烃，烯烃，一氧化碳和醇偶联生成官能化的酯。当链烯醇用作受体链烯时，伴随分子内酯化的三组分偶联反应进行，得到内酯。钯二聚体复合物[Pd 2（CNMe）6 ] [PF 6 ] 2已知在光辐照条件下会发生均裂，在这些三组分或四组分偶联反应中，它作为催化剂发挥了很好的作用。在这种金属/自由基杂化体系中，Pd自由基和酰基自由基都是关键参与者，并且立体化学研究证实了羰基化步骤是通过自由基羰基化机理进行的。
• Vicinal C-Functionalization of Alkenes. Pd/Light-Induced Multicomponent Coupling Reactions Leading to Functionalized Esters and Lactones
  作者：Akira Fusano、Shuhei Sumino、Takahide Fukuyama、Ilhyong Ryu

  DOI：10.1021/ol200536h

  日期：2011.4.15

  Under photoirradiation conditions using a xenon light, and in the presence of PdCl2(PPh3)(2) as a catalyst, four-component coupling reactions comprising of alpha-substituted iodoalkanes, alkenes, carbon monoxide, and alcohols proceeded smoothly to give functionalized esters in good yields. When alkenyl alcohols were used as acceptor alkenes, three-component coupling reactions accompanied by intramolecular esterification proceeded to give lactones in good yields. The present reaction system represents the vicinal C-functionalization of alkenes.
• JPH03251579A
  申请人：——

  公开号：JPH03251579A

  公开（公告）日：1991-11-11
• Lactone Synthesis Based on Atom Transfer Carbonylation
  作者：Sergio Kreimerman、Ilhyong Ryu、Satoshi Minakata、Mitsuo Komatsu

  DOI：10.1021/ol9913441

  日期：2000.2.1

  [GRAPHICS]Five- to seven-membered lactones were prepared from omega-hydroxyalkyl iodides and CO by atom transfer carbonylation without the need for transition metal catalysts, The reaction proceeds via a hybrid radical/ionic mechanism in which the intramolecular alcoholysis of an omega-hydroxyacyl iodide, arising from atom transfer carbonylation, leads to the lactone.