methyl 2,3-dihydroxy-2-phenyl-3-(4-bromophenyl)propanoate

• 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: methyl 2,3-dihydroxy-2-phenyl-3-(4-bromophenyl)propanoate
• 英文别名: methyl (2S,3S)-3-(4-bromophenyl)-2,3-dihydroxy-2-phenylpropanoate
• 化学式: C₁₆H₁₅BrO₄
• 分子量: 351.197
• InChiKey: XCAYZSQYFDVSDX-HOCLYGCPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  DL-扁桃酸甲酯 、 对溴苯甲醛 在 四氯化钛 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 methyl 2,3-dihydroxy-2-phenyl-3-(4-bromophenyl)propanoate 、 methyl 2,3-dihydroxy-2-phenyl-3-(4-bromophenyl)propanoate
  参考文献：
  名称：

  Reactivity of Methyl Mandelate−Ti(IV)-enediolate:  Oxidative Homocoupling versus Aldol and Direct Mannich-Type Syn-Diastereoselective Condensation

  摘要：

  Methyl mandelate undergoes quantitative oxidative homo-coupling on treatment with TiCl4/amine at room temperature. In the presence of ArCHO, quantitative syn-diastereo-selective aldol condensation takes over the dimerization, whereas exclusive Mannich-type syn-diastereo-selective reaction is observed in the presence of both ArCHO and PhNH2. The subsequent reactions of the title intermediate do not depend on how it is generated.

  DOI：

  10.1021/jo048279f

文献信息

• Efficient diastereoselective synthesis of α,β-Dihydroxyesters from methyl phenylglyoxylate and aldehydes mediated by Titanium Trichloride/Pyridine System
  作者：Angelo Clerici、Laura Clerici、Luciana Malpezzi、Ombretta Porta

  DOI：10.1016/0040-4020(95)00872-6

  日期：1995.11

  The reductive coupling of methyl phenylglyoxylate 2 with aliphatic and aromatic aldehydes 3, promoted by TiCl3/Py system in anhydrous THF. affords α,β-dihydroxyesters 4 in good yields (60–94%) and high syn-diastereoselectivity (up to 85%) The type of ligand at the metal ion necessary to achieve a high level of diastereocontrol and the possible mechanism involved are discussed

  TiCl 3 / Py体系在无水THF中促进了苯基乙醛酸甲酯2与脂肪族和芳香族醛3的还原偶联。可以提供高收率（60-94％）和高顺-非对映选择性（高达85％）的α，β-二羟基酯4，其中讨论了实现高水平非对映控制所必需的金属离子上的配体类型及其可能的机理
• Enantioselective Equilibration−Access to Chiral Aldol Adducts of Mandelic Acid Esters
  作者：Stefan Scholtis、Andreas Ide、Rainer Mahrwald

  DOI：10.1021/ol062252w

  日期：2006.11.9

  [Structure: see text] Syn-configured aldol products of mandelic acid esters and aldehydes were synthesized by the catalytic use of amines in the presence of titanium(IV) tert-butoxide. Used along with chiral N-methylephedrine, anti-configured alpha,beta-dihydroxyesters were isolated with a high degree of enantioselectivity for the first time.

  [结构：见正文]在叔丁醇钛（IV）的存在下，通过胺的催化合成了扁桃酸酯和醛的顺式构筑的羟醛产物。与手性N-甲基麻黄碱一起使用时，首次以高对映选择性分离了抗构型的α，β-二羟基酯。
• Unusual Oxidative Cleavage of Methyl Diphenyltartrate Promoted by Titanium Tetrachloride/Pyridine System
  作者：Angelo Clerici、Laura Clerici、Ombretta Porta

  DOI：10.1021/jo00108a001

  日期：1995.2