ethyl 2,3-diphenyl-3-hydroxypropionate

• 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: ethyl 2,3-diphenyl-3-hydroxypropionate
• 英文别名: ethyl 3-hydroxy-2,3-diphenylpropanoate；erythro-3-Hydroxy-2,3-diphenyl-propionsaeure-aethylester；ethyl (2R,3R)-3-hydroxy-2,3-diphenylpropanoate
• 化学式: C₁₇H₁₈O₃
• 分子量: 270.328
• InChiKey: RWYUOIPANURTLR-CVEARBPZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl 2,3-diphenyl-3-hydroxypropionate 在 lithium aluminium tetrahydride 、 oxonium 作用下， 以 吡啶 为溶剂， 生成 (1S,2S)-1,2-二苯基丙烷-1-醇
  参考文献：
  名称：

  一种利用金属锡合成β-羟基酯的新方法

  摘要：

  用氢化铝锂还原氯化亚锡制备的金属锡或活化金属锡，与α-卤代酯平稳反应生成烯醇锡，然后在温和条件下与羰基化合物反应，水解后生成β-羟基酯。产量。

  DOI：

  10.1246/cl.1982.161
• 作为产物：
  描述：

  α-溴苯乙酸乙酯 在 tin 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 ethyl 2,3-diphenyl-3-hydroxypropionate 、 ethyl 2,3-diphenyl-3-hydroxypropionate
  参考文献：
  名称：

  一种利用金属锡合成β-羟基酯的新方法

  摘要：

  用氢化铝锂还原氯化亚锡制备的金属锡或活化金属锡，与α-卤代酯平稳反应生成烯醇锡，然后在温和条件下与羰基化合物反应，水解后生成β-羟基酯。产量。

  DOI：

  10.1246/cl.1982.161

文献信息

• Enantioselective synthesis of anti- and syn-β-hydroxy-α-phenyl carboxylates via boron-mediated asymmetric aldol reaction
  作者：P. Veeraraghavan Ramachandran、Prem B. Chanda

  DOI：10.1039/c3cc40860d

  日期：——

  enantioselective synthesis of anti- and syn-beta-hydroxy-alpha-phenyl carboxylates has been achieved by the proper choice of solvent, temperature, alkoxy group, and amine for the diisopinocampheylboron-mediated asymmetric enolization-aldolization of phenylacetates. The pure diastereomers can be readily separated by column chromatography.

  抗和SYN-β-羟基-α-苯基羧酸酯的试剂控制的，diastereo-和对映选择性合成已经通过溶剂，温度，烷氧基，胺为diisopinocampheylboron介导的非对称的烯醇化-缩醛反应的适当选择来实现苯乙酸酯。可以通过柱色谱法容易地分离纯的非对映异构体。
• An Efficient Cobalt(I)-Catalysed Reformatsky Reaction using α-Chloro Esters
  作者：Marco Lombardo、Alessandra Gualandi、Filippo Pasi、Claudio Trombini

  DOI：10.1002/adsc.200600378

  日期：2007.2.5

  An efficient cobalt(I)-catalysed Reformatsky reaction using α-chloro esters has been developed. The catalyst is prepared by reducing the cobalt(II) chloride (5 %)/1,2-bis(diphenylphosphino)ethane (dppe)(5 %)/zinc iodide (10 %) system with zinc metal in acetonitrile in the presence of both the α-chloro ester and the carbonyl compound; good to excellent conversions to β-hydroxy esters are obtained at

  已开发出一种高效的钴（I）催化的使用α-氯代酯的Reformatsky反应。通过在乙腈存在下用锌金属还原氯化钴（II）（5％）/ 1,2-双（二苯基膦基）乙烷（dppe）（5％）/碘化锌（10％）体系来制备催化剂。 α-氯酯和羰基化合物都；在室温下2.5小时内，可以很好地转化为β-羟基酯。
• Overriding effect of temperature over reagent and substrate size for boron-mediated aldol reaction of methyl phenylacetate
  作者：P. Veeraraghavan Ramachandran、Prem B. Chanda

  DOI：10.1016/j.tetlet.2013.08.106

  日期：2013.10

  The enolization temperature overrides all other aspects, including the sterics of the alkyl group of the boron reagent and the alkoxy group of the ester during the enolboration-aldolization of phenylacetates. This study has led to the first n-Bu2BOTf-mediated anti-selective aldol reaction of an ester. (C) 2013 Elsevier Ltd. All rights reserved.
• Canceill,J. et al., Bulletin de la Societe Chimique de France, 1966, p. 2653 - 2658
  作者：Canceill,J. et al.

  DOI：——

  日期：——
• Enolboration. 6. Dicyclohexyliodoborane, a Versatile Reagent for the Stereoselective Synthesis of Either Z or E Enolates from Representative Esters
  作者：Kumaraperumal Ganesan、Herbert C. Brown

  DOI：10.1021/jo00088a012

  日期：1994.5

  A smooth, rapid, quantitative, and highly stereoselective synthesis of either Z or E enolates from representative esters has been achieved with dicyclohexyliodoborane, Chx(2)BI, in the presence of a suitable tertiary amine, such as triethylamine or N,N-diisopropylethylamine. A systematic investigation of the enolboration of ethyl propionate and ethyl phenylacetate, as model esters, by the various Chx(2)BX and BX-9-BBN reagents (X = OMs, I, and Br) established Chx(2)BI as the preferred reagent in terms of yield and selectivity. Further study of representative esters (RCH(2)-COOR') with Chx(2)BI established that the steric requirements of both the alkyl group (R) at the ct-position and the alkoxy group (OR') play a significant role in controlling the enolate geometry. The steric requirements of the amine (R''N-3) also contribute considerably to the stereoselectivity of the reaction, The present study provides a simple procedure for the synthesis of Z or E enol borinates from representative esters (RCH(2)COOR') using the combined stereodirecting effects of the alkyl (R) and the alkoxy (OR') groups. These enol borinates are highly reactive with aldehydes at temperatures as low as -78 degrees C and are exceptionally stereoselective even at 0 degrees C, In this exploratory study, the synthesis of stereoselective enolates from representative esters (RCH(2)COOR') using Chx(2)BI/R''N-3 is discussed, with special emphasis on the effects of the steric requirements of R and OR' in controlling the enolate geometry.