ethyl 2-(2-phenyloxiran-2-yl)acrylate | 253310-66-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: ethyl 2-(2-phenyloxiran-2-yl)acrylate
• 英文别名: Ethyl 2-(2-phenyloxiran-2-yl)prop-2-enoate
• CAS: 253310-66-6
• 化学式: C₁₃H₁₄O₃
• 分子量: 218.252
• InChiKey: GLLNDNQUXBGHIV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl 2-(2-phenyloxiran-2-yl)acrylate 在 硼烷四氢呋喃络合物 作用下， 反应 24.0h， 以76%的产率得到(E)-4-Hydroxy-2-methyl-3-phenyl-but-2-enoic acid ethyl ester
  参考文献：
  名称：

  A convenient synthesis of functionalized vinylepoxides

  摘要：

  Functionalized vinylepoxides were synthesized, in high yields, from alpha-bromoaldehydes and -ketones via vinylalumination, followed by cyclization with K2CO3 or KF under non-aqueous conditions. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)01642-1
• 作为产物：
  描述：

  ethyl 2-(2-bromo-1-hydroxy-1-phenylethyl)acrylate 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 6.0h， 以88%的产率得到ethyl 2-(2-phenyloxiran-2-yl)acrylate
  参考文献：
  名称：

  A convenient synthesis of functionalized vinylepoxides

  摘要：

  Functionalized vinylepoxides were synthesized, in high yields, from alpha-bromoaldehydes and -ketones via vinylalumination, followed by cyclization with K2CO3 or KF under non-aqueous conditions. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)01642-1

文献信息

• BF3·OEt2 Catalyzed Cascade [4 + 2] Benzannulation of Vinyloxiranes with Coumarins to Construct Benzocoumarin Derivatives
  作者：Yafei Wang、Yujia Wang、Jiaxin Qu、Tongtong Yang、Yining Zhang、Chunhao Yuan、Hongchao Guo、Chang Wang

  DOI：10.1021/acs.joc.4c00742

  日期：2024.7.5

  BF3·OEt2-catalyzed cascade cyclization reaction of vinyloxirane with coumarin is described, affording the benzocoumarin derivatives with moderate to excellent yields (72–92%). The reaction demonstrates exceptional substrate tolerance and has been extensively explored for its potential in drug development, including scale-up experiments, functional group transformations, and screening of the products for anticancer

  描述了 BF 3 ·OEt 2催化的乙烯基环氧乙烷与香豆素的级联环化反应，以中等至优异的收率 (72–92%) 提供苯并香豆素衍生物。该反应表现出卓越的底物耐受性，并因其在药物开发中的潜力而得到广泛探索，包括放大实验、官能团转化和产品抗癌活性筛选。此外，反应机制已通过中间捕获和控制实验得到严格验证。此外，该反应代表了不常见的非金属催化的乙烯基环氧乙烷分子间环化。
• Vinylalumination for the Synthesis of Functionalized Allyl Alcohols, Vinylepoxides, and α-Alkylidene-β-hydroxy-γ-lactones
  作者：P. Veeraraghavan Ramachandran、Michael T. Rudd、Thomas E. Burghardt、M. Venkat Ram Reddy

  DOI：10.1021/jo034954u

  日期：2003.11.1

  A modified hydroalumination protocol for the preparation of [alpha-(ethoxycarbonyl)vinyl]diisobutyl-aluminum and its beta-methyl or -phenyl analogues was developed. These vinylaluminum reagents react with aldehydes and ketones to provide the corresponding functionalized allyl alcohols in good to excellent yields. Perfluoroalkyl and -aryl carbonyl compounds, alpha-keto esters, alpha-acyl cyanides, and alpha-acetylenic ketones provide the corresponding alpha-hydroxyalkenes in high yields. The allyl alcohol product ratios from the vinylalumination of unsymmetrical alpha-diketones with [alpha-(ethoxycarbonyl)vinyl] diisobutylaluminum and its beta-methyl or -phenyl analogues depend on the steric and electronic environments of the ketones as well as the reagents. The products from the vinylalumination of alpha-bromoaldehydes and -ketones were cyclized With K2CO3 or KF under nonaqueous conditions to provide functionalized vinylepoxides in high yields. Vinylaluminations of keto-protected pyruvaldehyde provided the products, which were converted to alpha-alkylidene-beta-hydroxy-gamma-lactones.