(R)-diethyl 2-(1-(4-chlorophenyl)-3-oxo-3-phenylpropyl)malonate

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物
• 英文名称: (R)-diethyl 2-(1-(4-chlorophenyl)-3-oxo-3-phenylpropyl)malonate
• 英文别名: diethyl 2-[(1R)-1-(4-chlorophenyl)-3-oxo-3-phenylpropyl]propanedioate
• 化学式: C₂₂H₂₃ClO₅
• 分子量: 402.875
• InChiKey: ZFMAUBPWSKIYBL-SFHVURJKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  28
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  69.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  4-氯查耳酮 、 丙二酸二乙酯 在 C₅₆H₆₂N₆O₂⁽²⁺⁾*2Br^(1-) 、 sodium hydroxide 作用下， 以 水 、 甲苯 为溶剂， 反应 2.0h， 以94%的产率得到(R)-diethyl 2-(1-(4-chlorophenyl)-3-oxo-3-phenylpropyl)malonate
  参考文献：
  名称：

  使用手性相转移催化剂的迈克尔加成反应中对映选择性的意外溶剂/取代基依赖性转化

  摘要：

  带有5,5'-双（甲基）-2,2'-联吡啶1基团的新菊苣盐显示出对溶剂/取代基的对映选择性逆转。当在两个小时内将查尔酮与丙二酸二乙酯不对称迈克尔加成查耳酮时用作手性相转移催化剂时，这些催化剂在较低的碱和冷条件下会导致较高的化学收率（最高98％）和对映体过量（最高99％）。

  DOI：

  10.1016/j.tetlet.2015.07.074

文献信息

• Unexpected solvent/substitution-dependent inversion of the enantioselectivity in Michael addition reaction using chiral phase transfer catalysts
  作者：Ponmuthu Kottala Vijaya、Sepperumal Murugesan、Ayyanar Siva

  DOI：10.1016/j.tetlet.2015.07.074

  日期：2015.9

  New cinchonium salts bearing 5,5′-bis(methyl)-2,2′-bipyridine 1 group show solvent/substitution-dependent reversal of enantioselectivity. When used as chiral phase transfer catalyst in the asymmetric Michael addition of chalcones with diethylmalonate within two hours these catalysts result in high chemical yield (up to 98%) and enantiomeric excess (up to 99%) under lower concentrations of base and cold

  带有5,5'-双（甲基）-2,2'-联吡啶1基团的新菊苣盐显示出对溶剂/取代基的对映选择性逆转。当在两个小时内将查尔酮与丙二酸二乙酯不对称迈克尔加成查耳酮时用作手性相转移催化剂时，这些催化剂在较低的碱和冷条件下会导致较高的化学收率（最高98％）和对映体过量（最高99％）。
• Highly enantioselective Michael addition of diethyl malonate to chalcones catalyzed by cinchona alkaloids-derivatived bifunctional tertiary amine-thioureas bearing multiple hydrogen-bonding donors
  作者：Yulong Liu、Xie Wang、Xiaoyun Wang、Wei He

  DOI：10.1039/c4ob00203b

  日期：——

  Chalcones are still challenge substrates in Michael reactions, and only limited success has been achieved. This work describes a highly enantioselective Michael addition of diethyl malonate with chalcones catalyzed by cinchona alkaloids-derivatived bifunctional tertiary amine-thioureas bearing multiple hydrogen-bonding donors.

  查耳酮仍然是迈克尔反应中的挑战底物，仅取得了有限的成功。这项工作描述了由金鸡纳生物碱衍生的双官能叔胺-硫脲携带多个氢键供体催化的丙二酸二乙酯与查耳酮的高度对映选择性迈克尔加成反应。
• Organocatalytic Enantioselective Conjugate Additions to Enones
  作者：Jian Wang、Hao Li、Liansuo Zu、Wei Jiang、Hexin Xie、Wenhu Duan、Wei Wang

  DOI：10.1021/ja065187u

  日期：2006.10.1

  Conjugate addition reactions of a wide range of nucleophilic enol species with enones, catalyzed by a cinchona alkaloid derived thiourea organocatalyst, have been developed with attending good yields and high enantioselectivities under a mild reaction condition. The general method provides an efficient approach to the preparation of versatile building blocks possessing various functional groups.

  在温和的反应条件下，由金鸡纳生物碱衍生的硫脲有机催化剂催化的各种亲核烯醇与烯酮的共轭加成反应已得到发展，具有良好的产率和高对映选择性。通用方法为制备具有各种官能团的通用构件提供了一种有效的方法。
• Highly Enantioselective Asymmetric Michael Addition Reactions with New Chiral Multisite Phase-Transfer Catalysts
  作者：Ayyanar Siva、Sivamani Jayaraman、Duraimurugan Kumaraguru、Jesin Arockiam、Subha Paulpandian、Balasaravanan Rajendiran

  DOI：10.1055/s-0033-1339124

  日期：——

  enantioselective Michael addition reactions of diethyl malonate to various chalcones have been achieved under mild chiral multisite phase-transfer reaction conditions by the successful utilization of 2,4,6-(triscinchoniummethyl)phenyl-1,3,5-triazines as new chiral quaternary ammonium catalysts. This simple asymmetric Michael addition process was found to be quite effective and to obtain Michael adducts with

  通过成功利用 2,4,6-(triscinchoniummethyl)phenyl-1,3,5-triazines 作为新的手性季铵盐，在温和的手性多位点相转移反应条件下实现了丙二酸二乙酯与各种查耳酮的高对映选择性迈克尔加成反应铵催化剂。发现这种简单的不对称迈克尔加成过程非常有效，并且以非常好的产率和对映体过量获得迈克尔加合物。
• Highly enantioselective Michael addition reactions with new trimeric chiral phase transfer catalysts
  作者：Arockiam Jesin Beneto、Jayaraman Sivamani、Veeramanoharan Ashokkumar、Rajendiran Balasaravanan、Kumaraguru Duraimurugan、Ayyanar Siva

  DOI：10.1039/c4nj02395a

  日期：——

  New types of mesitylene based tri-site containing asymmetric quaternary ammonium salts 9a and 9b have been prepared and used as efficient chiral phase transfer catalysts for enantioselective Michael addition reactions between the chalcones and diethylmalonate under mild reaction conditions such as lower concentration of base, catalyst and ultrasonic conditions with very good chemical yields (up to

  制备了新型的均三甲苯基三位不对称季铵盐9a和9b，并将其用作有效的手性相转移催化剂，用于在温和的反应条件下，如碱，催化剂和催化剂的较低浓度下，查尔酮与丙二酸二乙酯之间进行对映选择性迈克尔加成反应。超声波条件，化学收率非常好（高达98％）和ee的化学收率（高达99％）。