(RR,SS)-2-hydroxy-3-methyl-2-phenyl-4-pentenoic acid | 82731-61-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (RR,SS)-2-hydroxy-3-methyl-2-phenyl-4-pentenoic acid
• 英文别名: 2-hydroxy-3-methyl-2-phenylpent-4-enoic acid；(2S,3S)-2-hydroxy-3-methyl-2-phenylpent-4-enoic acid
• CAS: 82731-61-1
• 化学式: C₁₂H₁₄O₃
• 分子量: 206.241
• InChiKey: ZUYRXYKAXAVWDB-CABZTGNLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  but-2-enyl 2-oxo-2-phenylacetate 在 silver(I) 4-methylbenzenesulfonate 、 1,1-di-tert-butyl-2,2-dimethylsilirane 、 pyridine hydrofluoride 作用下， 以 甲苯 为溶剂， 反应 16.0h， 以62%的产率得到(RR,SS)-2-hydroxy-3-methyl-2-phenyl-4-pentenoic acid
  参考文献：
  名称：

  Silylene transfer to α-keto esters and application to the synthesis of γ-lactones

  摘要：

  Disubstituted alpha-hydroxy acids have been synthesized by metal-catalyzed silylene transfer to alpha-keto esters. A range of substituents are tolerated in the transformation with the exception of branched groups at the vinylic position. The alpha-hydroxy acid products can be converted into gamma-lactones using a variety of lactonization conditions. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.05.066

文献信息

• The stereoselective crotylboration of alpha-oxocarboxylic acids
  作者：Zhe Wang、Xian-Jun Meng、George W. Kabalka

  DOI：10.1016/s0040-4039(00)93527-5

  日期：1991.10

  acids in a highly stereocontrolled manner. The reaction presumably proceeds through a bicyclic transition state. The alpha-carboxylic substituent exerts a remarkable effect on the rate, regio- and stereoselectivities of the reaction; homoallylic alpha-hydroxycarboxylic acids are formed with regio- and stereoselectivities approach 100%.

  巴豆基硼酸酯与α-氧代羧酸以高度立体可控的方式反应。该反应大概通过双环过渡态进行。α-羧基取代基对反应的速率，区域选择性和立体选择性具有显着影响。形成均一的α-羟基羧酸，其区域和立体选择性接近100％。
• Synthesis of Tertiary α-Hydroxy Acids by Silylene Transfer to α-Keto Esters
  作者：Brett E. Howard、K. A. Woerpel

  DOI：10.1021/ol702148x

  日期：2007.10.1

  alpha-Keto esters can be converted into alpha-hydroxy acids in a single flask involving metal-catalyzed silylene transfer, 6 pi-electrocyclization, Ireland-Claisen rearrangement, and hydrolysis. This reaction sequence is stereoselective and tolerates alkyl- and aryl-substituted a-keto ester substrates as well as an alpha-imino ester.
• Ester-enolate Claisen rearrangement of lactic acid derivatives
  作者：Paul A. Bartlett、Donna J. Tanzella、James F. Barstow

  DOI：10.1021/jo00141a025

  日期：1982.9
• Silylene transfer to α-keto esters and application to the synthesis of γ-lactones
  作者：Brett E. Howard、K.A. Woerpel

  DOI：10.1016/j.tet.2009.05.066

  日期：2009.8

  Disubstituted alpha-hydroxy acids have been synthesized by metal-catalyzed silylene transfer to alpha-keto esters. A range of substituents are tolerated in the transformation with the exception of branched groups at the vinylic position. The alpha-hydroxy acid products can be converted into gamma-lactones using a variety of lactonization conditions. (C) 2009 Elsevier Ltd. All rights reserved.