Benzoic acid 3-hydroxy-2-methyl-1-phenyl-pentyl ester

• 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: Benzoic acid 3-hydroxy-2-methyl-1-phenyl-pentyl ester
• 英文别名: (3-hydroxy-2-methyl-1-phenylpentyl) benzoate
• 化学式: C₁₉H₂₂O₃
• 分子量: 298.382
• InChiKey: DWCPAIFJGCBJCM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.99
• 重原子数：
  22.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  46.53
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  1-羟基-2-甲基-1-苯基戊烷-3-酮 、 苯甲醛 在 titanium(IV) tetrabutoxide 、 辛可尼丁 作用下， 以59%的产率得到[(1R,2R,3R,4S,5S)-3,5-dihydroxy-2,4-dimethyl-1,5-diphenyl] benzoate
  参考文献：
  名称：

  Enantioselective Direct Aldol-Tishchenko Reaction:  Access to Chiral Stereopentads

  摘要：

  The aldol-Tishchenko reaction of aromatic aldehydes in the presence of titanium(IV) tertbutoxide and amino alcohols is described. When used with cinchona alkaloids, stereopentads were isolated for the first time with a high degree of diastereo- and enantioselectivity.

  DOI：

  10.1021/ol0517675

文献信息

• Asymmetric aldol-Tishchenko reaction catalyzed by Yb-complexes with basic amino acid-derived ligands
  作者：Maciej Stodulski、Agnieszka Mamińska、Jacek Mlynarski

  DOI：10.1016/j.tetasy.2011.02.026

  日期：2011.2

  Simple amino acid-derived esters have been identified as promising chiral sources for the ytterbium-catalyzed aldol-Tishchenko reaction of aromatic aldehydes with aliphatic ketones. The 1,3-anti-diols with three stereogenic centers were isolated in excellent yields, complete anti-diastereocontrol and enantioselectivities of up to 50% ee.

  简单的氨基酸衍生的酯已被认为是promising催化芳香族醛与脂肪族酮的羟醛-季琴科反应的手性来源。具有优异的产率，完全的抗-非甾体控制和对映体选择性高达50％ee的具有三个立体生成中心的1,3-抗二醇类化合物被分离出来。
• The first example of a catalytic asymmetric aldol-Tishchenko reaction of aldehydes and aliphatic ketones
  作者：Jacek Mlynarski、Marcin Mitura

  DOI：10.1016/j.tetlet.2004.08.134

  日期：2004.10

  condensation––Evans–Tishchenko reduction of aldehydes and ketones. Chiral ytterbium complexes were found to catalyze the condensation of aromatic aldehydes with 3-pentanone (and other ketones) giving rise to the anti-1,3-diol monoesters in good yield, and with high diastereocontrol and moderate levels of enantioselectivity. Three adjacent stereogenic centers are created in one reaction sequence in acyclic systems

  已经筛选了路易斯酸和手性配体的多种组合，以进行对映选择性的直接串联羟醛缩合反应–埃文斯–季申科还原醛和酮。发现手性配合物催化芳族醛与3-戊酮（和其他酮）的缩合反应，从而以高收率，高非对映异构控制度和中等对映选择性水平产生抗-1,3-二醇单酯。在无环系统的一个反应序列中创建了三个相邻的立体生成中心。
• Enantioselective Direct Aldol-Tishchenko Reaction:  Access to Chiral Stereopentads
  作者：Kerstin Rohr、Robert Herre、Rainer Mahrwald

  DOI：10.1021/ol0517675

  日期：2005.9.1

  The aldol-Tishchenko reaction of aromatic aldehydes in the presence of titanium(IV) tertbutoxide and amino alcohols is described. When used with cinchona alkaloids, stereopentads were isolated for the first time with a high degree of diastereo- and enantioselectivity.