(S)-ethyl 2-hydroxy-4-oxo-2-phenylpentanoate | 959129-20-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 酮酸及其衍生物
• 英文名称: (S)-ethyl 2-hydroxy-4-oxo-2-phenylpentanoate
• 英文别名: 2-hydroxy-4-oxo-2-phenylpentanoic acid ethyl ester；ethyl (2S)-2-hydroxy-4-oxo-2-phenylpentanoate
• CAS: 959129-20-5
• 化学式: C₁₃H₁₆O₄
• 分子量: 236.268
• InChiKey: ZVOAUPXAFNLGFM-ZDUSSCGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  ethyl (2S)-2-hydroxy-2-phenyl-4-tri(propan-2-yl)silyloxypent-4-enoate 在 盐酸 作用下， 以 乙醇 为溶剂， 反应 0.08h， 以100%的产率得到(S)-ethyl 2-hydroxy-4-oxo-2-phenylpentanoate
  参考文献：
  名称：

  手性双阳离子钯(II)配合物对甲硅烷基烯醇醚酮酯-烯反应构建季碳的对映选择性催化

  摘要：

  可以实现双阳离子 SEGPHOS-Pd 配合物催化的酮酯 - 烯与甲硅烷基烯醇醚反应，以高产率和对映选择性生产具有季碳中心的烯产物。甚至可以进行更低的催化剂负载量（高达 0.01 mol%），而不会显着降低产率和对映选择性；这将为手性路易斯酸催化的工业应用打开大门。

  DOI：

  10.1021/ja076539f

文献信息

• Direct asymmetric aldol reaction of acetone with α-ketoesters catalyzed by primary–tertiary diamine organocatalysts
  作者：Zhaoqin Jiang、Yixin Lu

  DOI：10.1016/j.tetlet.2010.02.044

  日期：2010.4

  Novel primary–tertiary diamine organocatalysts derived from l-serine were utilized to promote enantioselective aldol reaction of acetone with α-ketoesters. The desired products were obtained in high yields and with good to excellent enantioselectivities (up to 95% ee).

  衍生自1-丝氨酸的新型伯-叔二胺有机催化剂被用于促进丙酮与α-酮酸酯的对映选择性醛醇缩合反应。以高收率和良好至优异的对映选择性（高达95％ee）获得所需产物。
• In Situ Formed Bifunctional Primary Amine-Imine Catalyst for Asymmetric Aldol Reactions of α-Keto Esters
  作者：Xi Zhu、Aijun Lin、Ling Fang、Wei Li、Chengjian Zhu、Yixiang Cheng

  DOI：10.1002/chem.201100200

  日期：2011.7.18

  In prime condition: The hydrolysis of a chiral diimine precursor can be carried out by a Brønsted acid to form an in situ primary amine–imine intermediate as a bifunctional primary aminocatalyst, which promoted direct asymmetric aldol reactions between α‐keto esters and ketones in high yields (up to 88 %) and with excellent enantioselectivities (see scheme; R1, R2, R4=alkyl; R3=aryl).

  在最佳条件下：手性二亚胺前体的水解可通过布朗斯台德酸进行，形成原位伯胺-亚胺中间体，作为双官能伯氨基催化剂，从而促进α-酮酯与酮之间的直接不对称醛醇缩合反应。产率（高达88％）并且具有优异的对映选择性（参见方案； R 1，R 2，R 4＝烷基； R 3＝芳基）。
• (1,2-Diaminoethane-1,2-diyl)bis(<i>N</i>-methylpyridinium) Salts as a Prospective Platform for Designing Recyclable Prolinamide-Based Organocatalysts
  作者：Vladislav G. Lisnyak、Alexander S. Kucherenko、Edward F. Valeev、Sergei G. Zlotin

  DOI：10.1021/acs.joc.5b01555

  日期：2015.10.2

  A new efficient and highly recyclable organocatalyst has been developed for asymmetric cross-aldol reactions under neat conditions in ketone–ketone, ketone–aldehyde, and aldehyde–aldehyde systems. The catalyst features two prolinamide fragments and a C2-symmetrical (1,2-diaminoethane-1,2-diyl)bis(N-methylpyridinium) group. The catalyst retained high activity and excellent stereoselection over the operating

  在酮-酮，酮-醛和醛-醛体系中，在纯净条件下开发了一种用于不对称交叉羟醛反应的新型高效且高度可回收的有机催化剂。该催化剂具有两个脯氨酰胺片段和一个C 2对称的（1,2-二氨基乙烷-1,2-二基）双（N-甲基吡啶鎓）基团。在超过830小时（25个循环）的工作时间内，该催化剂保持了高活性和出色的立体选择性。从头开始的理论研究解释了所设计的非对映异构有机催化剂的产物的绝对构型和不同的立体诱导水平。
• Enantioselective direct aldol reaction of α-keto esters catalyzed by (Sa)-binam-d-prolinamide under quasi solvent-free conditions
  作者：Santiago F. Viózquez、Abraham Bañón-Caballero、Gabriela Guillena、Carmen Nájera、Enrique Gómez-Bengoa

  DOI：10.1039/c2ob25224d

  日期：——

  (Sa)-Binam-D-prolinamide (20 mol%), instead of (Sa)-binam-L-prolinamide, in combination with chloroacetic acid (100 mol%) is an efficient organocatalyst for the direct aldol reaction between α-keto esters as electrophiles and alkyl and α-functionalised ketones, under quasi solvent-free conditions, providing access to highly functionalised chiral quaternary γ-keto α-hydroxyesters with up to 92% ee.

  （S a）-Binam- D-脯氨酰胺（20 mol％）代替（S a）-binam- L-脯氨酰胺与氯乙酸（100 mol％）结合使用是一种有效的有机催化剂，用于α之间的直接羟醛反应-酮酯作为亲电子试剂以及烷基和α-官能化的酮，在准无溶剂条件下，可提供ee高达92％的高度官能化的手性季式γ-酮α-羟基酯。
• Asymmetric aldol reactions in ketone/ketone systems catalyzed by ionic liquid-supported C2-symmetrical organocatalyst
  作者：Sergei V. Kochetkov、Alexander S. Kucherenko、Sergei G. Zlotin

  DOI：10.1016/j.mencom.2015.05.002

  日期：2015.5

  Ionic liquid-supported (1,S,2S)- and (1R,2R)-1,2-bis[(S)-prolinamido]-1,2-diphenylethanes act as organocatalysts in asymmetric aldol reactions of acetone with a-keto esters or trifluoroacetophenone providing high yields and from moderate to high enantioselectivity. Recycling of the catalyst with a gradual decrease in conversion and ee values is possible.