dimethyl (R)-2-phenylglutarate | 56523-52-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: dimethyl (R)-2-phenylglutarate
• 英文别名: Pentanedioic acid, 2-phenyl-, dimethyl ester, (R)-；dimethyl (2R)-2-phenylpentanedioate
• CAS: 56523-52-5
• 化学式: C₁₃H₁₆O₄
• 分子量: 236.268
• InChiKey: YPDDMZUWEYJXHM-LLVKDONJSA-N

物化性质

• 沸点：
  317.2±30.0 °C(Predicted)
• 密度：
  1.111±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  dimethyl 2-phenylpentanedioate 在 chiral OD-column 作用下， 以 正己烷 、 异丙胺 为溶剂， 生成 dimethyl (S)-2-phenylglutarate 、 dimethyl (R)-2-phenylglutarate
  参考文献：
  名称：

  自由基环化中的立体控制：速率确定步骤的变化

  摘要：

  带有手性2,4-戊二醇系链的酯的α-碳自由基的分子内环化显示，当自由基碳原子具有烷基取代基时，立体选择性低，而当取代基具有较高的选择性时，则可以生成单一的立体异构体（纯度> 99％）是芳基。选择性的差异可归因于从构象过程到环化过程的速率确定步骤的变化。

  DOI：

  10.1021/ol101370x

文献信息

• New synthetic strategy to highly symmetric chiral macrocycles from carbohydrate derivatives
  作者：Cristina Vicent、Manuel Martín-Lomas、Soledad Penadés*

  DOI：10.1016/s0040-4020(01)81039-5

  日期：1989.1

  A simple strategy for the synthesis of highly symmetric macrocycles incorporating carbohydrates is presented. The application of this strategy to the synthesis of optically active tetra-gluco-24-crown-8 (1), bis-gluco-15-crown-5 (3), and bis-gluco-21-crown-8 (5) is described. Preliminary studies showed that macrocycles 1, 3 and 5 complex ammonium salts. These macrocyclic compounds have been used as

  提出了一种简单的合成碳水化合物的高对称大环化合物的策略。该策略在光学活性四葡萄糖-24-冠-8（1），双葡萄糖-15-冠-5（3）和双葡萄糖-21-冠-8（5）的合成中的应用。描述。初步研究表明，大环1，3和5复杂铵盐。这些大环化合物已被用作α-苯基乙酸甲酯向丙烯酸甲酯的不对称迈克尔加成反应中的催化剂。
• Conjugate additions of the crown-potassium enolate complexes
  作者：Mayumi Takasu、Hiroaki Wakabayashi、Kyoji Furuta、Hisashi Yamamoto

  DOI：10.1016/s0040-4039(00)88481-6

  日期：——

  Achiral and chiral crowns complexed with potassium bases catalyze the Michael additions of enolates to cycloalkenones.

  与钾碱复合的非手性和手性冠催化烯醇化物向环烯酮的迈克尔加成反应。
• Simple chiral crown ethers complexed with potassium tert-butoxide as efficient catalysts for asymmetric Michael additions
  作者：Shin Aoki、Shigeki Sasaki、Kenji Koga

  DOI：10.1016/s0040-4039(01)93942-5

  日期：1989.1

  Simple C2-symmetric chiral crown ether 1 complexed with KOtBu was found to work as an efficient chiral catalyst in Michael additions to cause high asymmetric induction. The results with various chiral crown ethers as catalysts suggest that diaxial-like conformation of the vicinal methyl groups of 1·potassium enolate complex is responsible for the chiral induction.

  发现简单的C 2对称手性冠醚1与KO t Bu络合可在迈克尔加成反应中作为有效的手性催化剂，引起高度不对称诱导。用各种手性冠醚作为催化剂的结果表明1 ·烯醇钾复合物的邻位甲基的双轴样构象是手性诱导的原因。
• Asymmetric Michael addition and deracemization of enolate by chiral crown ether
  作者：László Töke、Péter Bakó、György M. Keser″u、Melinda Albert、László Fenichel

  DOI：10.1016/s0040-4020(97)10271-x

  日期：1998.1

  Crown ethers anellated to glucose units have been used to catalyse the enantioselective Michael addition of methyl phenylacetate to methyl acrylate in high chemical yields in up to 84% enantiomeric excess. A novel CH-acid deracemization has also been discovered and the mechanistic rationale of the asymmetric induction is discussed. The proposed mechanism of the addition was also substantiated by molecular

  与葡萄糖单元成对的冠醚已被用于催化苯乙酸甲酯向丙烯酸甲酯的对映选择性迈克尔加成，其化学产率高，对映体过量高达84％。还发现了一种新型的CH-酸脱氮方法，并讨论了不对称诱导的机理原理。分子力学计算也证实了所提出的加成机理。
• New chiral crown ethers derived from camphor and their application to asymmetric Michael addition. First attempts to rationalize enantioselection by AM1 and AMBER calculations
  作者：Ernesto Brunet、Ana M. Poveda、Dolores Rabasco、Enrique Oreja、Luis M. Font、Manohar Singh Batra、Juan C. Rodriguez-Ubis

  DOI：10.1016/s0957-4166(00)86246-1

  日期：1994.5

  optically active crown ethers derived from (1R)-(+)-camphor is described. The mechanism of their catalytic effect upon the Michael addition of phenylacetate to acrylate is discussed in terms of kinetic vs. thermodynamic control in the formation of the catalytic ion-pair complexes. The relative basicity of the complexes formed between the alkaline metals and the unprotonated chiral crown ethers plays an important

  描述了衍生自（1 R）-（+）-樟脑的新型旋光冠醚的合成。从动力学对动力学的角度讨论了它们在苯乙酸迈克尔加成到丙烯酸酯上的催化效应机理。催化离子对络合物形成过程中的热力学控制。碱金属和未质子化的手性冠醚之间形成的配合物的相对碱性在立体化学结果中起重要作用。AMBER和AM1计算支持在动力学控制下进行获得最佳ee（83％）的反应。