(S)-(+)-4-ethyl-4-phenylpent-2-enedioic acid 1-ethyl ester 5-methyl ester | 177532-29-5

• 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: (S)-(+)-4-ethyl-4-phenylpent-2-enedioic acid 1-ethyl ester 5-methyl ester
• 英文别名: (S)-(+)-1-ethyl 5-methyl 4-ethyl-4-phenylglutaconate；1-O-ethyl 5-O-methyl (E,4S)-4-ethyl-4-phenylpent-2-enedioate
• CAS: 177532-29-5
• 化学式: C₁₆H₂₀O₄
• 分子量: 276.332
• InChiKey: NHRKNGMIYPSJBI-PCUGXKRQSA-N

物化性质

• 沸点：
  369.0±30.0 °C(Predicted)
• 密度：
  1.080±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  20
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-(+)-4-ethyl-4-phenylpent-2-enedioic acid 1-ethyl ester 5-methyl ester 在 platinum(IV) oxide sodium hydroxide 、 氢气 作用下， 以 乙醇 、 乙酸乙酯 为溶剂， 25.0 ℃ 、101.33 kPa 条件下， 反应 30.0h， 生成 (S)-(+)-2-ethyl-2-phenylglutaric acid
  参考文献：
  名称：

  Asymmetric construction of benzylic quaternary carbons from chiral malonates: Formal synthesis of both (−)- and (+)-aminoglutethimides AG and analogues

  摘要：

  From a single chiron (R)-(+)-5, available with high enantiomeric excess (97%) by enzymatic hydrolysis (PLE acetonic powder) of a malonate, were prepared convenient precursors of aminoglutethimides (-)-AG-1 and (+)-AG-1. This versatile method also allows preparation of the b-hydroxy ester (R)-9 and its enantiomer (S)-9 as well as the glutethimides (S)-4 and (R)-4 and other analogues. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0957-4166(96)00122-x
• 作为产物：
  描述：

  (2R)-2-methoxycarbonyl-2-phenylbutanoic acid 在 甲醇 、 sodium tetrahydroborate 、 草酰氯 、 二甲基亚砜 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 、 N,N-二甲基甲酰胺 、 lithium chloride 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 9.0h， 生成 (S)-(+)-4-ethyl-4-phenylpent-2-enedioic acid 1-ethyl ester 5-methyl ester
  参考文献：
  名称：

  Asymmetric construction of benzylic quaternary carbons from chiral malonates: Formal synthesis of both (−)- and (+)-aminoglutethimides AG and analogues

  摘要：

  From a single chiron (R)-(+)-5, available with high enantiomeric excess (97%) by enzymatic hydrolysis (PLE acetonic powder) of a malonate, were prepared convenient precursors of aminoglutethimides (-)-AG-1 and (+)-AG-1. This versatile method also allows preparation of the b-hydroxy ester (R)-9 and its enantiomer (S)-9 as well as the glutethimides (S)-4 and (R)-4 and other analogues. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0957-4166(96)00122-x

文献信息

• Catalytic Enantioselective Synthesis of Quaternary All-Carbon Stereogenic Centers. Preparation of α,α‘-Disubstituted β,γ-Unsaturated Esters through Cu-Catalyzed Asymmetric Allylic Alkylations
  作者：Kerry E. Murphy、Amir H. Hoveyda

  DOI：10.1021/ol047331r

  日期：2005.3.1

  prepared from commercially available materials, are used to promote Cu-catalyzed asymmetric allylic alkylations of alpha,beta-unsaturated esters bearing a gamma-phosphate with various alkylzinc reagents. These transformations lead to the formation of alpha,alpha'-dialkyl-beta,gamma-unsaturated esters in high yields as well as high regio- (re) and enantioselectivities (ee).

  [反应：见正文]易于从市售材料制备的基于肽的手性配体，用于通过各种烷基锌试剂促进Cu催化的带有γ-磷酸酯的α，β-不饱和酯的不对称烯丙基烷基化反应。这些转化导致以高收率以及高区域选择性和对映选择性ee形成α，α′-二烷基-β，γ-不饱和酯。