(R)-isopropyl 2-(2-chlorophenyl)-2-hydroxyacetate | 1242001-70-2

• 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: (R)-isopropyl 2-(2-chlorophenyl)-2-hydroxyacetate
• 英文别名: propan-2-yl (2R)-2-(2-chlorophenyl)-2-hydroxyacetate
• CAS: 1242001-70-2
• 化学式: C₁₁H₁₃ClO₃
• 分子量: 228.675
• InChiKey: SHIQJYQOEUQWFR-SNVBAGLBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2 -氯苯基氧乙酸 在 草酰氯 、 3,3’-di(9-phenylanthryl)BINOL phosphoric acid 、 二丁基镁 、 三乙胺 、 N,N-二甲基甲酰胺 、 儿萘酚硼烷 作用下， 以 二氯甲烷 、 甲苯 、 均三甲苯 为溶剂， 反应 24.0h， 生成 (S)-isopropyl 2-(2-chlorophenyl)-2-hydroxyacetate 、 (R)-isopropyl 2-(2-chlorophenyl)-2-hydroxyacetate
  参考文献：
  名称：

  对映和化学选择性布朗斯台德酸/ Mg（nBu）2催化儿茶酚硼烷还原α-酮酯。

  摘要：

  已开发出第一对映体和化学选择性布朗斯台德酸催化的儿茶酚硼烷还原α-酮酯。α-羟基酯是在温和的反应条件下以实际上定量的产率和优异的对映选择性而获得的。稍作修饰，即可得到两种对映体，而不会损失任何选择性。

  DOI：

  10.1039/c4cc00427b

文献信息

• Rhodium-Catalyzed Asymmetric Addition of Arylboronic Acids to Glyoxylates: Access to Optically Active Substituted Mandelic Acid Esters
  作者：Diao Chen、Jian-Guo Liu、Xu Zhang、Ming-Hua Xu

  DOI：10.1055/s-0037-1610722

  日期：2019.9

  A rhodium-catalyzed enantioselective addition of glyoxylates to arylboronic acids promoted by a simple chiral sulfinamide-based olefin ligand under mild reaction conditions is described. The reaction provides access to a variety of optically active substituted mandelic acid esters in good yields with up to 83% ee. The catalytic system is also applicable to pyruvate addition. The synthetic utility of

  描述了在温和的反应条件下，由简单的手性亚磺酰胺基烯烃配体促进的铑催化对映选择性加成乙醛酸到芳基硼酸。该反应提供了多种光学活性取代的扁桃酸酯，收率高达 83% ee。该催化体系也适用于丙酮酸加成。抗血小板药物氯吡格雷的正式合成强调了该方法的合成效用。
• A rapid and green approach to chiral α-hydroxy esters: asymmetric transfer hydrogenation (ATH) of α-keto esters in water by use of surfactants
  作者：Lu Yin、Xian Jia、Xingshu Li、Albert S.C. Chan

  DOI：10.1016/j.tetasy.2009.08.019

  日期：2009.9

  A series of α-hydroxy esters were rapidly prepared (1.5 h) from α-keto esters via asymmetric transfer hydrogenation (ATH) in water by the use of surfactants for the first time. This green method, catalyzed by a water-soluble and recyclable Ru(II) complex, gave moderate to high enantioselectivities (up to 99.7% ee) with DTAB as an additive and HCOONa as the hydrogen source.

  首次使用表面活性剂，通过水中的不对称转移氢化（ATH），由α-酮酸酯快速制备了一系列α-羟基酯（1.5小时）。这种绿色方法由水溶性和可循环利用的Ru（II）配合物催化，用DTAB作为添加剂，HCOONa作为氢源，具有中等到较高的对映选择性（高达99.7％ee）。
• Simply air: Vanadium-catalyzed oxidative kinetic resolution of methyl o-chloromandelate by ambient air
  作者：Lu Yin、Xian Jia、Xing Shu Li、Albert S.C. Chan

  DOI：10.1016/j.cclet.2010.03.002

  日期：2010.7

  Vanadium-catalyzed oxidative kinetic resolution (OKR) of methyl o-chloromandelate 2a, key intermediate of the well-known oral antiplatelet agent (S)-clopidogrel, was achieved by ambient air for the first time. The air oxidation system, which was composed of vanadium and tridentate Schiff base ligands derived from amino alcohols and salicylaldehyde derivatives, afforded an efficient and economic approach

  钒催化的甲基的氧化动力学拆分（OKR）ø -chloromandelate 2a中，公知的口服抗血小板剂（的关键中间体小号） -氯吡格雷，通过环境空气首次实现。空气氧化系统由衍生自氨基醇和水杨醛衍生物的钒和三齿Schiff碱配体组成，为具有高对映选择性（> 99％ee）的目标中间体提供了一种有效而经济的方法。
• METHOD FOR PRODUCTION OF OPTICALLY ACTIVE -HYDROXYCARBOXYLIC ACID
  申请人：Daiichi Fine Chemical Co., Ltd.

  公开号：EP1930441A1

  公开（公告）日：2008-06-11

  An efficient method for producing an optically active α -hydroxycarboxylic acid represented by the following general formula (I) [A represents a residue of a 5- or 6-membered cyclic compound, * indicates a carbon atom in the S- or R-configuration, X represents hydrogen atom or an alkyl group having 1 to 4 carbon atoms], which comprises the step of treating a corresponding ester compound (not optically pure) with cell bodies or a culture, or a processed product or an extract thereof of a microorganism of the genus Leifsonia, genus Cylindrocarpon, genus Verticillium, or the like.

  一种生产由以下通式(I)代表的光学活性α-羟基羧酸的有效方法[A代表5或6元环状化合物的残基，*表示S或R构型的碳原子，X代表氢原子或具有1至4个碳原子的烷基]、其中包括用 Leifsonia 属、Cylindrocarpon 属、Verticillium 属等微生物的细胞体或培养物或加工产品或其提取物处理相应的酯类化合物（非光学纯）的步骤。
• Method for Producing Optically Active Alpha-Hydroxycarboxylic Acid
  申请人：Sakamoto Keiji

  公开号：US20080311636A1

  公开（公告）日：2008-12-18

  An efficient method for producing an optically active α-hydroxycarboxylic acid represented by the following general formula (I) [A represents a residue of a 5- or 6-membered cyclic compound, * indicates a carbon atom in the S- or R-configuration, X represents hydrogen atom or an alkyl group having 1 to 4 carbon atoms], which comprises the step of treating a corresponding ester compound (not optically pure) with cell bodies or a culture, or a processed product or an extract thereof of a microorganism of the genus Leifsonia , genus Cylindrocarpon , genus Verticillium , or the like.