methyl (R)-(+)-3-hydroxy-2-methylenehexanoate

• 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: methyl (R)-(+)-3-hydroxy-2-methylenehexanoate
• 英文别名: (R)-methyl 3-hydroxy-2-methylenehexanoate；methyl (3R)-3-hydroxy-2-methylidenehexanoate
• 化学式: C₈H₁₄O₃
• 分子量: 158.197
• InChiKey: YMHOPFPBSLGXDP-SSDOTTSWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  11
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.62
• 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：

  methyl (R)-(+)-3-hydroxy-2-methylenehexanoate 在 叔丁基过氧化氢 、 甲基锂 作用下， 以 四氢呋喃 、 正己烷 、 甲苯 为溶剂， 以62%的产率得到
  参考文献：
  名称：

  Study of the stereoselectivity of the nucleophilic epoxidation of 3-hydroxy-2-methylene esters

  摘要：

  The diastereoselectivity of the nucleophilic epoxidation of 3-hydroxy-2-methylene esters has been studied. The 3-hydroxy-2-methylene esters were obtained through a Morita-Baylis-Hillman reaction. The resulting epoxyesters were treated with thiophenol for transformation into 2,3-dihydroxy-2-((phenylthio)methyl), which upon treatment with triphosgene afforded the corresponding cyclic carbonates. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.11.014
• 作为产物：
  描述：

  正丁醛 、 丙烯酸甲酯（MA） 在 三乙烯二胺 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 48.0h， 以99%的产率得到methyl (R)-(+)-3-hydroxy-2-methylenehexanoate
  参考文献：
  名称：

  Study of the stereoselectivity of the nucleophilic epoxidation of 3-hydroxy-2-methylene esters

  摘要：

  The diastereoselectivity of the nucleophilic epoxidation of 3-hydroxy-2-methylene esters has been studied. The 3-hydroxy-2-methylene esters were obtained through a Morita-Baylis-Hillman reaction. The resulting epoxyesters were treated with thiophenol for transformation into 2,3-dihydroxy-2-((phenylthio)methyl), which upon treatment with triphosgene afforded the corresponding cyclic carbonates. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.11.014

文献信息

• Resolution of α-methylene-β-hydroxy esters catalyzed by free and immobilized Pseudomonas sp. lipase
  作者：M.G. Nascimento、Sandra P. Zanotto、Sı́lvia P. Melegari、Luciano Fernandes、Marcus Mandolesi Sá

  DOI：10.1016/j.tetasy.2003.08.015

  日期：2003.10

  Kinetic resolutions of α-methylene-β-hydroxy esters (Baylis–Hillman products) have been performed via enzymatic enantioselective transesterification with Pseudomonas sp. lipase (PSL), free or immobilized in poly(ethylene) oxide (PEO), silica gel and montmorillonite K10, under different reaction conditions. The corresponding (R)-(+)-acetates from alkyl-substituted racemic alcohols were obtained with

  α-亚甲基-β-羟基酯（Baylis–Hillman产品）的动力学拆分已通过假单胞菌属酶的酶促对映选择性酯交换进行。脂肪酶（PSL），在不同的反应条件下游离或固定在聚环氧乙烷（PEO），硅胶和蒙脱土K10中。使用己烷中的PSL / PEO系统和乙酸乙烯酯作为酰化剂，得到ee> 99％且具有优异至中等转化率的烷基取代的外消旋醇，相应的（R）-（+）-乙酸酯。在这些实验条件下，萘基取代的羟基酯是惰性的。