ethyl 3-hydroxy-2,4-dimethylpentanoate

• 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 3-hydroxy-2,4-dimethylpentanoate
• 英文别名: ethyl (2S,3R)-3-hydroxy-2,4-dimethylpentanoate
• 化学式: C₉H₁₈O₃
• 分子量: 174.24
• InChiKey: QVEUGQREVQOQNV-JGVFFNPUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  12
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1-ethoxy-1-trimethylsiloxy-2-methylthio-1-propene 在 N-(p-toluenesulfonyl)-L-valine 、 sodium tetrahydroborate 、 硼烷四氢呋喃络合物 、 氢气 、 nickel dichloride 作用下， 以 乙醇 为溶剂， 反应 18.17h， 生成 ethyl 3-hydroxy-2,4-dimethylpentanoate
  参考文献：
  名称：

  的高度对映选择性合成顺式-和反-丙酸酯醛醇而不diastereoselection在与手性oxazaborolidinone促进的醛醇缩合反应的甲硅烷烯酮缩醛衍生自2-（甲硫基）丙酸

  摘要：

  在由2-（甲硫基）丙酸乙基酯衍生的新型甲硅烷基乙烯酮缩醛的手性氧杂硼硼烷酮促进的醛醇缩合反应中，以高收率和高对映选择性获得了包含α-甲硫基的顺式和反式醛醇产物的混合物。醛。随后的脱硫导致有效制备基本上可分离的基本上对映纯的顺式和反丙酸的羟醛。

  DOI：

  10.1016/s0957-4166(98)00159-1

文献信息

• Boron-Mediated Aldol Reaction of Carboxylic Esters:  Complementary Anti- and Syn-Selective Asymmetric Aldol Reactions
  作者：Tadashi Inoue、Ji-Feng Liu、Dana C. Buske、Atsushi Abiko

  DOI：10.1021/jo0257896

  日期：2002.7.1

  The boron-mediated aldol reaction of carboxylic esters is described in detail. Contrary to the general belief that carboxylic esters are inert under the condition of the boron enolate formation, propionate esters are enolized with certain combinations of a boron triflate and an amine. More importantly, the stereochemical course of the aldol reaction can be controlled by the judicious selection of the

  详细描述了硼介导的羧酸酯的羟醛反应。与通常认为羧酸酯在烯醇硼形成的条件下是惰性的一般看法相反，丙酸酯被三氟甲磺酸硼和胺的某些组合烯醇化。更重要的是，可以通过明智地选择烯醇化试剂来控制羟醛反应的立体化学过程。用c-Hex2BOTf和三乙胺处理丙酸酯可制得抗醛醇缩合产物，而用Bu2BOTf和二异丙基乙胺处理丙酸酯可在与醛反应后选择性地生成顺醛醇缩合产物。已经开发了具有结构相关的，容易获得的手性去甲麻黄碱衍生的丙酸酯的互补抗和顺选择性不对称醛醇缩合反应。
• A Divergent Synthesis of Essentially Enantiopure<i>syn</i>- and<i>anti</i>-Propionate Aldol Adducts Based on the Chiral 1,3,2-Oxazaborolidin-5-one-Promoted Asymmetric Aldol Reaction Followed by Diastereoselective Radical Reduction
  作者：Syun-ichi Kiyooka、Kazi Abuds Shahid

  DOI：10.1246/bcsj.74.1485

  日期：2001.8

  Essentially, enantiopure syn- and anti-propionate aldol adducts were divergently synthesized using a novel strategy which utilizes both the highly enantioselective 1,3,2-oxazaborolidin-5-one-promoted aldol reaction with a ketene silyl acetal derived from ethyl 2-bromo propionate and a highly diastereoselective radical debromination reaction. These procedures provide yields that increase to a level

  本质上，对映纯的合成和反丙醇醛加合物是使用一种新的策略不同地合成的，该策略利用高度对映选择性的 1,3,2-oxazaborolidin-5-one-促进的醛醇反应与衍生自乙基 2-溴的乙烯酮甲硅烷基缩醛丙酸盐和高度非对映选择性的自由基脱溴反应。这些程序提供的产率增加到可用于实际合成的水平。
• Titanocene(III)-Promoted Reformatsky Additions
  作者：J. D. Parrish、Daniel R. Shelton、R. Daniel Little

  DOI：10.1021/ol035269c

  日期：2003.10.1

  A novel method for the promotion of Reformatsky-like reactions is presented. The technique employs titanocene(Ill) chloride as a mild and homogeneous single-electron reductant. The reactions are rapid, operationally simple, and compatible with a wide range of functionalities. These additions are also anti diastereoselective.
• A practical synthesis of essentially enantiopure syn-propionate aldols using a chiral oxazaborolidinone-promoted asymmetric aldol reaction coupled with radical reduction
  作者：Syun-ichi Kiyooka、Kazi A. Shahid、Mostofa A. Hena

  DOI：10.1016/s0040-4039(99)01278-2

  日期：1999.8

  Essentially enantiopure syn-propionate aldols (>98% ee) were prepared by a chiral oxazaborolidinone-promoted asymmetric aldol reaction, followed by a diastereoselective radical reduction with Bu3SnH and Et3B, which was carried out under chelation control. (C) 1999 Elsevier Science Ltd. All rights reserved.
• Concerning the Boron-Mediated Aldol Reaction of Carboxylic Esters
  作者：Atsushi Abiko、Ji-Feng Liu、Satoru Masamune

  DOI：10.1021/jo960252b

  日期：1996.1.1