ethyl 3-hydroxy-2-methyl-5-phenylpentanoate

• 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-methyl-5-phenylpentanoate
• 英文别名: ethyl (2S,3S)-3-hydroxy-2-methyl-5-phenylpentanoate
• 化学式: C₁₄H₂₀O₃
• 分子量: 236.311
• InChiKey: ONUJGTBQPQEEBB-AAEUAGOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 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 3-hydroxy-2-methyl-5-phenylpentanoate 在 水 、 lithium hydroxide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 0.5h， 以98%的产率得到3-hydroxy-2-methyl-5-phenylpentanoic acid
  参考文献：
  名称：

  MNBA-Mediated β-Lactone Formation: Mechanistic Studies and Application for the Asymmetric Total Synthesis of Tetrahydrolipstatin

  摘要：

  Various beta-lactones were prepared from beta-hydroxycarboxylic acids by intramolecular dehydration condensation using MNBA, an effective coupling reagent, along with a nucleophilic catalyst. The transition state that provides the desired 4-membered ring model system is disclosed by density functional theory (DFT) calculations, and the structural features of the transition form are discussed. This method was successfully applied to the asymmetric total synthesis of tetrahydrolipstatin (THL), an antiobestic drug used in clinical treatment to inhibit the activity of pancreatic lipase.

  DOI：

  10.1021/jo300139r
• 作为产物：
  描述：

  苯丙醛 在 正丁基锂 、 二异丙胺 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 5.0h， 生成 ethyl 3-hydroxy-2-methyl-5-phenylpentanoate
  参考文献：
  名称：

  MNBA-Mediated β-Lactone Formation: Mechanistic Studies and Application for the Asymmetric Total Synthesis of Tetrahydrolipstatin

  摘要：

  Various beta-lactones were prepared from beta-hydroxycarboxylic acids by intramolecular dehydration condensation using MNBA, an effective coupling reagent, along with a nucleophilic catalyst. The transition state that provides the desired 4-membered ring model system is disclosed by density functional theory (DFT) calculations, and the structural features of the transition form are discussed. This method was successfully applied to the asymmetric total synthesis of tetrahydrolipstatin (THL), an antiobestic drug used in clinical treatment to inhibit the activity of pancreatic lipase.

  DOI：

  10.1021/jo300139r

文献信息

• Lewis Base Activation of Lewis Acids:  Catalytic, Enantioselective Addition of Silyl Ketene Acetals to Aldehydes
  作者：Scott E. Denmark、Gregory L. Beutner、Thomas Wynn、Martin D. Eastgate

  DOI：10.1021/ja047339w

  日期：2005.3.1

  The concept of Lewis base activation of Lewis acids has been reduced to practice for catalysis of the aldol reaction of silyl ketene acetals and silyl dienol ethers with aldehydes. The weakly acidic species, silicon tetrachloride (SiCl4), can be activated by binding of a strongly Lewis basic chiral phosphoramide, leading to in situ formation of a chiral Lewis acid. This species has proven to be a competent

  路易斯酸的路易斯碱活化的概念已被简化用于催化甲硅烷基乙烯酮缩醛和甲硅烷基二烯醇醚与醛的羟醛反应。弱酸性物质四氯化硅 (SiCl4) 可以通过结合强路易斯碱性手性磷酰胺而被激活，导致手性路易斯酸的原位形成。该物质已被证明是将乙酸酯、丙酸酯和异丁酸酯衍生的甲硅烷基乙烯酮缩醛与共轭和非共轭醛进行羟醛加成反应的有效催化剂。此外，还证明了甲硅烷基二烯醇醚的乙烯基羟醛反应。高水平的区域-，抗非对映-，
• Lewis Base Activation of Lewis Acids. Addition of Silyl Ketene Acetals to Aldehydes
  作者：Scott E. Denmark、Thomas Wynn、Gregory L. Beutner

  DOI：10.1021/ja0282947

  日期：2002.11.1

  olefinic aldehydes as well as aliphatic aldehydes (albeit more slowly) with excellent enantioselectivity. The homologous tert-butyldimethylsilyl ketene acetal of tert-butyl propanoate adds with nearly exclusive anti diastereoselectivity to a similar range of aldehydes also with excellent enantioselectivity. The origin of the slower reaction rate with aliphatic aldehydes is revealed to be the formation of chlorosilyl

  弱路易斯酸四氯化硅可以被催化量的手性双磷酰胺 (R,R)-3 活化，形成高反应性的手性三氯甲硅烷基阳离子，它是醛和甲硅烷基乙烯酮缩醛之间羟醛加成反应的极其有效的促进剂。乙酸甲酯的叔丁基二甲基甲硅烷基乙烯酮缩醛几乎立即添加到芳香族和烯烃醛以及脂肪族醛中（尽管速度更慢），具有出色的对映选择性。丙酸叔丁酯的同源叔丁基二甲基甲硅烷基乙烯酮缩醛为类似范围的醛类添加了几乎独有的抗非对映选择性，同时也具有出色的对映选择性。与脂肪醛反应速度较慢的原因是氯甲硅烷基醚加合物的形成。
• Uncatalyzed aldol reaction using a dimethylsilyl enolate and α-dimethylsilyl ester in N,N-dimethylformamide
  作者：Katsukiyo Miura、Hiroshi Sato、Kentaro Tamaki、Hajime Ito、Akira Hosomi

  DOI：10.1016/s0040-4039(98)00275-5

  日期：1998.4

  Dimethylsilyl enolates and alpha-dimethylsilyl esters reacted with aldehydes in N,N-dimethyl-formamide without an activator to give aldol adducts in moderate to good yields. Under the same conditions, the corresponding trimethylsilyl derivatives exhibited lower reactivities toward the aldol reaction. (C) 1998 Elsevier Science Ltd. All rights reserved.
• MNBA-Mediated β-Lactone Formation: Mechanistic Studies and Application for the Asymmetric Total Synthesis of Tetrahydrolipstatin
  作者：Isamu Shiina、Yuma Umezaki、Nobutaka Kuroda、Takashi Iizumi、Shunsuke Nagai、Takashi Katoh

  DOI：10.1021/jo300139r

  日期：2012.6.1

  Various beta-lactones were prepared from beta-hydroxycarboxylic acids by intramolecular dehydration condensation using MNBA, an effective coupling reagent, along with a nucleophilic catalyst. The transition state that provides the desired 4-membered ring model system is disclosed by density functional theory (DFT) calculations, and the structural features of the transition form are discussed. This method was successfully applied to the asymmetric total synthesis of tetrahydrolipstatin (THL), an antiobestic drug used in clinical treatment to inhibit the activity of pancreatic lipase.