3-(2-furyl)-3-hydroxy-2-methylene-propanoic acid 2-chloroethyl ester | 144261-82-5

• 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: 3-(2-furyl)-3-hydroxy-2-methylene-propanoic acid 2-chloroethyl ester
• 英文别名: 2-chloroethyl 2-[(furan-2-yl)(hydroxy)methyl]acrylate
• CAS: 144261-82-5
• 化学式: C₁₀H₁₁ClO₄
• 分子量: 230.648
• InChiKey: KPOTVEHWFVLDFO-UHFFFAOYSA-N

物化性质

• 沸点：
  343.2±42.0 °C(Predicted)
• 密度：
  1.287±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.65
• 重原子数：
  15.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  59.67
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  叔丁基二甲硅基三氟甲磺酸酯 、 3-(2-furyl)-3-hydroxy-2-methylene-propanoic acid 2-chloroethyl ester 在 2,6-二甲基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 0.75h， 以84%的产率得到2-chloroethyl 2-[(tert-butyldimethylsilyloxy)(furan-2-yl)methyl]acrylate
  参考文献：
  名称：

  A tandem Baylis–Hillman-singlet oxygen oxidation reaction for facile synthesis of γ-substituted γ-hydroxybutenolides

  摘要：

  A series of highly functionalised gamma-hydroxyacryl gamma-hydroxybutenolides, 2, were synthesised in 25-50% overall yields in two or three steps from 2-furfural using a tandem Baylis-Hillman-singlet oxygen oxidation reaction. Crown Copyright (C) 2008 Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.09.019
• 作为产物：
  描述：

  糠醛 、 丙烯酸氯乙酯 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以51%的产率得到3-(2-furyl)-3-hydroxy-2-methylene-propanoic acid 2-chloroethyl ester
  参考文献：
  名称：

  A tandem Baylis–Hillman-singlet oxygen oxidation reaction for facile synthesis of γ-substituted γ-hydroxybutenolides

  摘要：

  A series of highly functionalised gamma-hydroxyacryl gamma-hydroxybutenolides, 2, were synthesised in 25-50% overall yields in two or three steps from 2-furfural using a tandem Baylis-Hillman-singlet oxygen oxidation reaction. Crown Copyright (C) 2008 Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.09.019

文献信息

• The ‘Baylis - Hillman Reaction’ mechanism and applications revisited
  作者：Yves Fort、Marie Christine Berthe、Paul Caubere

  DOI：10.1016/s0040-4020(01)88227-2

  日期：1992.1

  It is shown that reaction of aryl, benzyl, alkyl and functionalised alkyl acrylic esters with benzaldehyde, in the presence of 1,4-diazabicyclo[2.2.2] octane, strongly depends upon the electronic and steric effects of the ester part. This influence is also observed in condensation of furfuraldehyde. Moreover, for the first time, it is shown that the overall condensation is equilibrated.