ethyl (+)-3-(2-chlorophenyl)-3-hydroxybutanoate

• 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: ethyl (+)-3-(2-chlorophenyl)-3-hydroxybutanoate
• 英文别名: Ethyl 3-(2-chlorophenyl)-3-hydroxybutanoate
• 化学式: C₁₂H₁₅ClO₃
• 分子量: 242.702
• InChiKey: DFDWFMVPEXNFAG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 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：

  邻氯苯乙酮 、 碘代醋酸乙酯 在 1,3-双(二苯基膦)丙烷 、 Dimethylzinc 、 copper(l) cyanide 、 (1S,2R)-1-苯基-2-(1-吡咯烷基)-1-丙醇 作用下， 以 二氯甲烷 、 甲基叔丁基醚 、 甲苯 为溶剂， 反应 20.0h， 以40%的产率得到ethyl (+)-3-(2-chlorophenyl)-3-hydroxybutanoate
  参考文献：
  名称：

  Copper-promoted enantioselective Reformatsky-type reaction with ketones

  摘要：

  Controlled living polymerization of a broad range of monomers is a radical process known as ATRP (atom transfer radical polymerization) and is mediated by a variety of metals. A complex of copper has been found to be the most efficient catalyst, with a copper(I)/copper(II) catalytic cycle. The radical, enantioselective catalytic Reformatsky reaction mediated by Me2Zn can be efficiently promoted by copper(I) complexes avoiding the use of other promoters such as air and oxidant, giving more reproducible and affordable conditions. The CuCN-mediated enantioselective addition of ethyliodoacetate to functionalized ketones is described in this paper. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.04.058

文献信息

• Indolinylmethanol catalyzed enantioselective Reformatsky reaction with ketones
  作者：Ning Lin、Miao-Miao Chen、Ren-Shi Luo、Yan-Qiu Deng、Gui Lu

  DOI：10.1016/j.tetasy.2010.11.004

  日期：2010.12

  A series of chiral indolinylmethanol ligands have been applied for the first time in the asymmetric Reformatsky reaction of an α-bromoester with ketones. In the presence of NiBr2 and zinc powder, up to 75% yield and 87% ee were obtained for a variety of aromatic and aliphatic ketones. The use of Ni(acac)2 resulted in 96% ee although the corresponding yield was low. This process provided a convenient

  在α-溴酸酯与酮的不对称Reformatsky反应中，首次应用了一系列手性吲哚基甲醇配体。在NiBr 2和锌粉的存在下，各种芳族和脂族酮的收率均达到75％，ee达到87％。Ni（acac）2的使用产生了96％的ee，尽管相应的收率很低。该方法提供了一种方便的方法来获得合成上有用的手性β-羟基酯。
• A Catalytic, Me2Zn-Mediated, Enantioselective Reformatsky Reaction With Ketones
  作者：Pier Giorgio Cozzi

  DOI：10.1002/anie.200504239

  日期：2006.4.28
• Copper-promoted enantioselective Reformatsky-type reaction with ketones
  作者：Fides Benfatti、Pier Giorgio Cozzi

  DOI：10.1016/j.tetasy.2010.04.058

  日期：2010.6

  Controlled living polymerization of a broad range of monomers is a radical process known as ATRP (atom transfer radical polymerization) and is mediated by a variety of metals. A complex of copper has been found to be the most efficient catalyst, with a copper(I)/copper(II) catalytic cycle. The radical, enantioselective catalytic Reformatsky reaction mediated by Me2Zn can be efficiently promoted by copper(I) complexes avoiding the use of other promoters such as air and oxidant, giving more reproducible and affordable conditions. The CuCN-mediated enantioselective addition of ethyliodoacetate to functionalized ketones is described in this paper. (C) 2010 Elsevier Ltd. All rights reserved.