(R)-2-甲酰基-2-苯基丁酸甲酯 | 177532-28-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: (R)-2-甲酰基-2-苯基丁酸甲酯
• 英文名称: (R)-methyl 2-ethyl-2-phenyl-3-oxopropionate
• 英文别名: methyl (R)-(+)-2-formyl-2-phenylbut-3-enoate；methyl (2R)-2-formyl-2-phenylbutanoate
• CAS: 177532-28-4
• 化学式: C₁₂H₁₄O₃
• 分子量: 206.241
• InChiKey: DSPIFYLRLXJCAU-LBPRGKRZSA-N

物化性质

• 沸点：
  293.5±28.0 °C(predicted)
• 密度：
  1.085±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.71
• 重原子数：
  15.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  43.37
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (R)-2-甲酰基-2-苯基丁酸甲酯 在 platinum(IV) oxide sodium hydroxide 、 氢气 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 lithium chloride 作用下， 以 乙醇 、 乙酸乙酯 为溶剂， 25.0 ℃ 、101.33 kPa 条件下， 反应 35.0h， 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 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 2.25h， 生成 (R)-2-甲酰基-2-苯基丁酸甲酯
  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。
• Asymmetric construction of benzylic quaternary carbons from chiral malonates: Formal synthesis of both (−)- and (+)-aminoglutethimides AG and analogues
  作者：Antoine Fadel、Sebastien Garcia-Argote

  DOI：10.1016/0957-4166(96)00122-x

  日期：1996.4

  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