Propynoic acid 4-hydroxy-butyl ester | 126199-91-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: Propynoic acid 4-hydroxy-butyl ester
• 英文别名: 4-Hydroxybutyl prop-2-ynoate
• CAS: 126199-91-5
• 化学式: C₇H₁₀O₃
• 分子量: 142.155
• InChiKey: CRMGCTWXMOYOHO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  10
• 可旋转键数：
  5
• 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：

  potassium selenocyanate 、 Propynoic acid 4-hydroxy-butyl ester 在 乳酸 、 水 作用下， 以96%的产率得到4-hydroxybutyl (Z)-3-selenocyanatoacrylate
  参考文献：
  名称：

  Sustainable routes for quantitative green selenocyanation of activated alkynes

  摘要：

  Most organic reactions require the usage of volatile organic compounds in the synthesis, work-up and purification processes, thus resulting in major environmental pollution and high manufacturing cost. By using cheap biomass lactic acid as the reaction media and catalyst, a sustainable protocol for the synthesis of Z-3-selenocyanatoacrylates and analogues through green selenocyanation of activated alkynes has been achieved. A principal advantage of this protocol is that the usage of organic volatile compounds can be avoided entirely, as the conversion of substrate is almost quantitative or quantitative with a minimal amount of lactic acid employed as reaction media, and the pure products can be conveniently collected through water precipitation. (C) 2019 Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences. Published by Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.cclet.2019.04.033
• 作为产物：
  描述：

  1,4-丁二醇 、 丙炔酸 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 乙醚 为溶剂， 反应 10.0h， 以66%的产率得到Propynoic acid 4-hydroxy-butyl ester
  参考文献：
  名称：

  改进的脂肪族丙炔酸酯的制备

  摘要：

  提出了一种基于N，N'-二环己基碳二亚胺4-二甲基氨基吡啶缩合的丙酸酯化反应的改进方法，该方法与伯，仲，烯丙基和均烯丙基醇均能获得良好的结果。反应条件温和。给出了一些限制。

  DOI：

  10.1016/s0040-4039(01)80735-8

文献信息

• A direct catalyst-free and stereoselective sulfonylation of propargyl esters for efficient synthesis of (Z)-β-sulfonyl enoates in water
  作者：Jun Jiang、Yundong Wu、Ruijia Wang、Yongzhao He、Chonghui Xu、Wei Deng、Zebing Zeng、Jiannan Xiang

  DOI：10.1016/j.tet.2016.09.037

  日期：2016.12

  Water-promoted sulfonylation of propargyl esters leading to highly regioselective and stereoselective formation of (Z)-β-sulfonyl enoates in excellent yields, by a simple, mild, and environmentally benign reaction procedure without employing any ligand or additive is reported.

  据报道，通过简单，温和且对环境无害的反应程序，无需使用任何配体或添加剂，丙炔酸酯的水促进的磺酰化导致（Z）-β-磺酰基烯酸酯的高度区域选择性和立体选择性的形成，产率极高。
• Improved preparation of aliphatic propynoic esters
  作者：L. Balas、B. Jousseaume、B. Langwost

  DOI：10.1016/s0040-4039(01)80735-8

  日期：1989.1

  An improved procedure of esterification of propynoic acid, based on the N, N′-dicyclohexylcarbodiimide 4-dimethylaminopyridine condensation, is presented, which gives good results with primary, secondary, allylic and homoallylic alcohols. Reactions conditions are mild. Some limitations are given.

  提出了一种基于N，N'-二环己基碳二亚胺4-二甲基氨基吡啶缩合的丙酸酯化反应的改进方法，该方法与伯，仲，烯丙基和均烯丙基醇均能获得良好的结果。反应条件温和。给出了一些限制。
• Sustainable routes for quantitative green selenocyanation of activated alkynes
  作者：Ling-Hui Lu、Zheng Wang、Weng Xia、Ping Cheng、Bo Zhang、Zhong Cao、Wei-Min He

  DOI：10.1016/j.cclet.2019.04.033

  日期：2019.6

  Most organic reactions require the usage of volatile organic compounds in the synthesis, work-up and purification processes, thus resulting in major environmental pollution and high manufacturing cost. By using cheap biomass lactic acid as the reaction media and catalyst, a sustainable protocol for the synthesis of Z-3-selenocyanatoacrylates and analogues through green selenocyanation of activated alkynes has been achieved. A principal advantage of this protocol is that the usage of organic volatile compounds can be avoided entirely, as the conversion of substrate is almost quantitative or quantitative with a minimal amount of lactic acid employed as reaction media, and the pure products can be conveniently collected through water precipitation. (C) 2019 Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences. Published by Elsevier B.V. All rights reserved.