ethyl 2(2,2,2-trichloro-1-hydroxyethyl)acrylate | 124778-91-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 英文名称: ethyl 2(2,2,2-trichloro-1-hydroxyethyl)acrylate
• 英文别名: ethyl 4,4,4-trichloro-3-hydroxy-2-methylenebutanoate；Ethyl 4,4,4-trichloro-3-hydroxy-2-methylidenebutanoate
• CAS: 124778-91-2
• 化学式: C₇H₉Cl₃O₃
• 分子量: 247.506
• InChiKey: RBPDBOIBTGQVMM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl 2(2,2,2-trichloro-1-hydroxyethyl)acrylate 在 吡啶 、 三溴化磷 、 potassium iodide 作用下， 以 乙醚 、 乙腈 为溶剂， 反应 2.0h， 生成 ethyl 4,4,4-trichloro-3-diethoxyphosphinoyl-2-methylenebutanoate
  参考文献：
  名称：

  McFadden, Helen G.; Harris, Roger L. N.; Jenkins, Colin L. D., Australian Journal of Chemistry, 1989, vol. 42, # 2, p. 301 - 314

  摘要：

  DOI：
• 作为产物：
  描述：

  三氯乙醛 、 丙炔酸乙酯 在 二异丁基氢化铝 、 N-甲基吗啉氧化物 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以87%的产率得到ethyl 2(2,2,2-trichloro-1-hydroxyethyl)acrylate
  参考文献：
  名称：

  Vinylalumination for the Synthesis of Functionalized Allyl Alcohols, Vinylepoxides, and α-Alkylidene-β-hydroxy-γ-lactones

  摘要：

  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.

  DOI：

  10.1021/jo034954u

文献信息

• Vinylalumination of fluoro-carbonyl compounds
  作者：P. Veeraraghavan Ramachandran、M. Venkat Ram Reddy、Michael T. Rudd、Javier Read de Alaniz

  DOI：10.1016/s0040-4039(98)01974-1

  日期：1998.11

  Ethyl acrylate and acrylonitrile fail to undergo efficient Baylis-Hillman reaction with fluoral, but provide good yields of products with pentafluorobenzaldehyde. Alternately, unsubstituted and beta-substituted [alpha- (ethoxycarbonyl)vinyl]aluminum react with perfluoroalkyl and -aryl aldehydes and ketones to provide the alpha-hydroxyalkenylated fluoroorganic compounds in good to excellent yields. (C) 1998 Elsevier Science Ltd. All rights reserved.
• MCFADDEN, HELEN G.;HARRIS, ROGER L. N.;JENKINS, COLIN L. D., AUSTRAL. J. CHEM., 42,(1989) N, C. 301-314
  作者：MCFADDEN, HELEN G.、HARRIS, ROGER L. N.、JENKINS, COLIN L. D.

  DOI：——

  日期：——