(S)-ethyl 2-(3-chlorophenyl)-2-hydroxyacetate | 190433-57-9

• 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: (S)-ethyl 2-(3-chlorophenyl)-2-hydroxyacetate
• 英文别名: ethyl 2-(3-chlorophenyl)-2-hydroxyacetate；Ethyl (S)-2-(3-chlorophenyl)-2-hydroxyacetate；ethyl (2S)-2-(3-chlorophenyl)-2-hydroxyacetate
• CAS: 190433-57-9
• 化学式: C₁₀H₁₁ClO₃
• 分子量: 214.649
• InChiKey: YXRWJRDEXVLHEI-VIFPVBQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 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：

  (3-chlorophenyl)magnesium bromide 在 二甲基苯基硅烷 、 C₅₂H₅₄ 、 三环己基膦 、 bis(pentafluorophenyl)borane 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 6.5h， 生成 (S)-ethyl 2-(3-chlorophenyl)-2-hydroxyacetate
  参考文献：
  名称：

  手性受阻路易斯对催化 1,2-二羰基化合物的高度对映选择性氢化硅烷化

  摘要：

  利用三环己基膦和从二炔原位衍生的手性烯基硼烷的组合作为受挫的路易斯对催化剂，首次成功实现了 1,2-二羰基化合物的高度对映选择性氢化硅烷化。以 52-98% 的收率和 86-99% 的 ee's 获得了多种光学活性 α-羟基酮和酯。

  DOI：

  10.1021/jacs.5b13104

文献信息

• Exploiting Cofactor Versatility to Convert a FAD‐Dependent Baeyer–Villiger Monooxygenase into a Ketoreductase
  作者：Jian Xu、Yongzhen Peng、Zhiguo Wang、Yujing Hu、Jiajie Fan、He Zheng、Xianfu Lin、Qi Wu

  DOI：10.1002/anie.201907606

  日期：2019.10.7

  thereby converting this CHMO into a ketoreductase, which can reduce a range of differently substituted aromatic α-keto esters. The improved, promiscuous reduction activity of the mutant enzyme in comparison to the wild-type enzyme results from a decrease in the distance between the carbonyl moiety of the substrate and the hydrogen atom on N5 of the reduced flavin adenine dinucleotide (FAD) cofactor, as

  环己酮单加氧酶（CHMOs）对天然拜耳-维利格（BV）反应显示出非常高的催化特异性，并且迄今尚未报道过混杂还原反应。不动杆菌属的野生型CHMO。发现NCIMB 9871具有还原芳族α-酮酯的固有的，混杂的能力，但是收率和立体选择性差。结构导向的定点诱变极大地提高了催化羰基还原活性（产率高达99％）和立体选择性（ee高达99％），从而将这种CHMO转化为酮还原酶，可以减少一系列不同取代的芳香族化合物。 α-酮酯。改进后的
• A New Class of Tunable Dendritic Diphosphine Ligands: Synthesis and Applications in the Ru-Catalyzed Asymmetric Hydrogenation of Functionalized Ketones
  作者：Baode Ma、Tingting Miao、Yihua Sun、Yanmei He、Ji Liu、Yu Feng、Hui Chen、Qing-Hua Fan

  DOI：10.1002/chem.201402709

  日期：2014.8.4

  dendritic 2,2′‐bis(diphenylphosphino)‐1,1′‐binaphthyl (BINAP) ligands was prepared by attaching polyaryl ether dendrons onto the four phenyl rings on the P atoms. Their ruthenium complexes were employed in the asymmetric hydrogenation of β‐ketoesters, α‐ketoesters, and α‐ketoamides to reveal the effects of dendron size on the catalytic properties. The second‐ and third‐generation catalysts exhibited excellent

  一系列可调的G 0 –G 3树枝状2,2'-双（二苯基膦基）-1,1'-联萘（BINAP）配体是通过将聚芳基醚树枝状分子连接到P原子上的四个苯环上而制备的。他们的钌配合物用于β-酮酸酯，α-酮酸酯和α-酮酰胺的不对称氢化反应，揭示了树枝状分子大小对催化性能的影响。第二代和第三代催化剂表现出优异的对映选择性，明显高于从小分子催化剂和第一代催化剂获得的对映选择性。分子模型表明，大的树枝状楔形物的结合会影响金属中心周围的空间环境。此外，
• CeCl₃·7H₂O: An Effective Additive in Ru-Catalyzed Enantioselective Hydrogenation of Aromatic α-Ketoesters
  作者：Qinghua Meng、Yanhui Sun、Virginie Ratovelomanana-Vidal、Jean Pierre Genêt、Zhaoguo Zhang

  DOI：10.1021/jo800228e

  日期：2008.5.1

  In the presence of catalytic amounts of CeCl3 center dot 7H(2)O, [RuCl(benzene)(S)-SunPhos]Cl is a highly effective catalyst for the asymmetric hydrogenation of aromatic alpha-ketoesters. A variety of ethyl alpha-hydroxy-alpha-arylacetates have been prepared in up to 98.3% ee with a TON up to 10 000. Challenging aromatic alpha-ketoesters with ortho substituents are also hydrogenated with high enantioselectivities. The addition of CeCl3 center dot 7H(2)O not only improves the enantioselectivity but also enhances the stability of the catalyst. The ratio of CeCl3 center dot 7H(2)O to [RuCl(benzene)(S)-SunPhos]Cl plays an important role in the hydrogenation reaction with a large substrate/catalyst ratio.
• Chiral Frustrated Lewis Pairs Catalyzed Highly Enantioselective Hydrosilylations of 1,2-Dicarbonyl Compounds
  作者：Xiaoyu Ren、Haifeng Du

  DOI：10.1021/jacs.5b13104

  日期：2016.1.27

  A highly enantioselective hydrosilylation of 1,2-dicarbonyl compounds was successfully realized for the first time utilizing the combination of tricyclohexylphosphine and chiral alkenylborane derived in situ from diyne as a frustrated Lewis pair catalyst. A variety of optically active α-hydroxy ketones and esters were obtained in 52-98% yields with 86-99% ee's.

  利用三环己基膦和从二炔原位衍生的手性烯基硼烷的组合作为受挫的路易斯对催化剂，首次成功实现了 1,2-二羰基化合物的高度对映选择性氢化硅烷化。以 52-98% 的收率和 86-99% 的 ee's 获得了多种光学活性 α-羟基酮和酯。