(S)-acetic acid (3-cyanophenyl)(4-hydroxymethylphenyl)methyl ester | 889118-11-0

• 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)-acetic acid (3-cyanophenyl)(4-hydroxymethylphenyl)methyl ester
• 英文别名: (S)-(3-Cyanophenyl)[4-(hydroxymethyl)phenyl]methyl acetate；[(S)-(3-cyanophenyl)-[4-(hydroxymethyl)phenyl]methyl] acetate
• CAS: 889118-11-0
• 化学式: C₁₇H₁₅NO₃
• 分子量: 281.311
• InChiKey: ZKEMPZYSUFEEDU-KRWDZBQOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  70.3
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,4-二羟基-3-丙基苯乙酮 、 (S)-acetic acid (3-cyanophenyl)(4-hydroxymethylphenyl)methyl ester 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 12.0h， 以24.5 g的产率得到(S)-acetic acid [4-(4-acetyl-3-hydroxy-2-propylphenoxymethyl)phenyl](3-cyanophenyl)methyl ester
  参考文献：
  名称：

  Optimized Catalytic Enantioselective Aryl Transfer Process Gives Access to mGlu2 Receptor Potentiators

  摘要：

  An asymmetric enantioselective aryl transfer reaction was developed to give access to the diarylmethanol 7 and ultimately acetate 2 which is useful for the preparation of mGlu2 receptor potentiators ( Scheme 3). The aryl transfer chemistry involved the preparation of a proposed arylalkylzinc species 14 from boroxine 16 and diethylzinc (DEZ), and reacting this mixture with aldehyde 5 in the presence of chiral ligand 15. During the course of optimizing the preparations of proposed intermediate 14 and diarylmethanol 7, an understanding of optimal stoichiometry and reaction times was gained through empirical observation, the use of solution IR, and analyzing off-gases via real time gas analysis/mass spectroscopy. The preparation of diarylmethanol 7 and subsequent conversion into acetate 2 required carefully selected workups, selective extractions, and azeotropic distillations to generate a series of stock solutions to accommodate oil intermediates that finally gave acetate 2 as a crystalline solid with > 99% ee.

  DOI：

  10.1021/op0602268
• 作为产物：
  描述：

  1-溴-4-叔丁基二甲基硅烷氧甲基苯 在 盐酸 、 4-二甲氨基吡啶 、 magnesium 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 正庚烷 、 水 、 1,2-二溴乙烷 、 乙腈 为溶剂， 反应 12.11h， 生成 (S)-acetic acid (3-cyanophenyl)(4-hydroxymethylphenyl)methyl ester
  参考文献：
  名称：

  Optimized Catalytic Enantioselective Aryl Transfer Process Gives Access to mGlu2 Receptor Potentiators

  摘要：

  An asymmetric enantioselective aryl transfer reaction was developed to give access to the diarylmethanol 7 and ultimately acetate 2 which is useful for the preparation of mGlu2 receptor potentiators ( Scheme 3). The aryl transfer chemistry involved the preparation of a proposed arylalkylzinc species 14 from boroxine 16 and diethylzinc (DEZ), and reacting this mixture with aldehyde 5 in the presence of chiral ligand 15. During the course of optimizing the preparations of proposed intermediate 14 and diarylmethanol 7, an understanding of optimal stoichiometry and reaction times was gained through empirical observation, the use of solution IR, and analyzing off-gases via real time gas analysis/mass spectroscopy. The preparation of diarylmethanol 7 and subsequent conversion into acetate 2 required carefully selected workups, selective extractions, and azeotropic distillations to generate a series of stock solutions to accommodate oil intermediates that finally gave acetate 2 as a crystalline solid with > 99% ee.

  DOI：

  10.1021/op0602268

文献信息

• Potentiators Of Glutamate Receptors
  申请人：AICHER Thomas Daniel

  公开号：US20090318481A1

  公开（公告）日：2009-12-24

  This application relates to a substituted hydroxyphenyl ketone compound of formula I, or a pharmaceutically acceptable salt thereof, a pharmaceutical composition thereof and its use in treating migraine. This application also relates to processes for preparing a compound of formula I, and intermediate compounds useful therein.

  本申请涉及一种公式I的取代羟基苯酮化合物，或其药学上可接受的盐，及其在治疗偏头痛中的应用，以及制备公式I化合物的过程和其中有用的中间体化合物的应用。
• Potentiators of Glutamate Receptors
  申请人：Eli Lilly and Company

  公开号：EP2441762A1

  公开（公告）日：2012-04-18

  The present invention provides compounds of formula I: pharmaceutical compositions thereof, and methods of using the same, processes or preparing the same, and intermediates thereof.

  本发明提供了式 I 的化合物： 其药物组合物、使用方法、制备方法及其中间体。
• US7598423B2
  申请人：——

  公开号：US7598423B2

  公开（公告）日：2009-10-06
• US7816523B2
  申请人：——

  公开号：US7816523B2

  公开（公告）日：2010-10-19
• US7803938B2
  申请人：——

  公开号：US7803938B2

  公开（公告）日：2010-09-28