(R)-1,2-bis(4-ethylphenyl)-2-hydroxyethanone | 1135459-35-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (R)-1,2-bis(4-ethylphenyl)-2-hydroxyethanone
• 英文别名: (R)-1,2-bis(4-ethylphenyl)-2-hydroxyethan-1-one；(R)-p-ethylbenzoin；(2R)-1,2-bis(4-ethylphenyl)-2-hydroxyethanone
• CAS: 1135459-35-6
• 化学式: C₁₈H₂₀O₂
• 分子量: 268.356
• InChiKey: OXCCBQFLIFFZGW-QGZVFWFLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  4-乙基苯甲醛 在 5a(S),10b(R)-5a,10b-dihydro-2-(pentafluorophenyl)-4H,6H-indeno[2,1-b][1,2,4]triazolo[4,3-d][1,4]oxazinium tetrafluoroborate 、 水 、 sodium carbonate 作用下， 反应 10.0h， 以86%的产率得到
  参考文献：
  名称：

  N-杂环卡宾催化的水中不对称苯偶姻反应

  摘要：

  已经开发了在水中的手性N-杂环卡宾催化的安息香缩合反应，提供了高产率到高对映选择性的α-羟基酮。在水不对称缩合反应中，提出了水作为质子穿梭体。

  DOI：

  10.1021/acs.joc.8b00481

文献信息

• Chiral iron complex catalyzed enantioselective oxidation of racemic benzoins
  作者：Pandi Muthupandi、Santosh Kumar Alamsetti、Govindasamy Sekar

  DOI：10.1039/b904021h

  日期：——

  An efficient, economic and environmentally friendly enantioselective oxidation of racemic benzoins (alpha-hydroxy ketones) catalyzed by a chiral iron complex has been developed using molecular oxygen as a terminal oxidant with good selectivity and excellent enantiomeric excess.

  使用分子氧作为末端氧化剂，具有良好的选择性和优异的对映体过量，已开发了一种由手性铁配合物催化的外消旋安息香（α-羟基酮）对映体的高效，经济和环境友好的对映选择性氧化。
• Galactose Oxidase Model: Biomimetic Enantiomer-Differentiating Oxidation of Alcohols by a Chiral Copper Complex
  作者：Santosh Kumar Alamsetti、Sreedevi Mannam、Pandi Mutupandi、Govindasamy Sekar

  DOI：10.1002/chem.200802064

  日期：2009.1.19

  GO for it! An enantiopure galactose oxidase (GO) enzyme model has been synthesized from readily available (R)‐binam and Cu(OTf)2 (see scheme; TEMPO=2,2,6,6‐tetramethyl‐piperidin‐1‐oxyl), and has been effectively used as an efficient chiral catalyst for the oxidative kinetic resolution of secondary alcohols. This is the first chiral copper‐catalyzed oxidative kinetic resolution of racemic benzoins and

  大胆试试吧！对映纯半乳糖氧化酶（GO）酶模型已从现成的（R）-比纳姆和Cu（OTf）2（参见方案; TEMPO = 2,2,6,6-四甲基-哌啶-1-氧）合成，并且已有效地用作仲醇的氧化动力学拆分的有效手性催化剂。这是外消旋安息香的第一个手性铜催化的氧化动力学拆分，也是合成高度重要的对映体富集的安息香的最简单方法。
• Solvent-Free Benzoin and Stetter Reactions with a Small Amount of NHC Catalyst in the Liquid or Semisolid State
  作者：Tadashi Ema、Yoshiko Nanjo、Sho Shiratori、Yuta Terao、Ryo Kimura

  DOI：10.1021/acs.orglett.6b03115

  日期：2016.11.4

  The intermolecular or intramolecular asymmetric benzoin reaction was catalyzed by a small amount of N-heterocyclic carbene (NHC) (0.2–1 mol %) under solvent-free conditions. The solvent-free intramolecular asymmetric Stetter reaction also proceeded efficiently with NHC (0.2–1 mol %). In some cases, even solid-to-solid or solid-to-liquid conversions took place with low catalyst loading (0.2–1 mol %)

  在无溶剂条件下，少量的N-杂环卡宾（NHC）（0.2-1 mol％）催化分子间或分子内不对称安息香反应。使用NHC（0.2–1 mol％），无溶剂的分子内不对称Stetter反应也能有效地进行。在某些情况下，即使在催化剂负载量较低（0.2–1摩尔％）的情况下，也可以进行固-固或固-液转化。
• Chiral Zn-catalyzed aerobic oxidative kinetic resolution of α-hydroxy ketones
  作者：Pandi Muthupandi、Govindasamy Sekar

  DOI：10.1016/j.tetasy.2011.02.025

  日期：2011.3

  The aerobic oxidative kinetic resolution of racemic alpha-hydroxy ketones was accomplished using a chiral Zn-quinine complex as the catalyst in the presence of molecular oxygen. The resulting optimized reaction conditions were applied to resolute different types of racemic alpha-hydroxy ketones and a maximum of 9.2 selectivity (s) was obtained with 88% ee for the recovered alpha-hydroxy ketone. (C) 2011 Elsevier Ltd. All rights reserved.
• N-Heterocyclic Carbene-Catalyzed Asymmetric Benzoin Reaction in Water
  作者：Jun Yan、Rong Sun、Kuangxi Shi、Kai Li、Limin Yang、Guofu Zhong

  DOI：10.1021/acs.joc.8b00481

  日期：2018.7.20

  A chiral N-heterocyclic carbene-catalyzed benzoin condensation reaction in water has been developed, affording α-hydroxy ketones in good to high yields and high enantioselectivities. Water was proposed as a proton shuttle in the aqueous asymmetric condensation reaction.

  已经开发了在水中的手性N-杂环卡宾催化的安息香缩合反应，提供了高产率到高对映选择性的α-羟基酮。在水不对称缩合反应中，提出了水作为质子穿梭体。