(2S,3R)-trans-(4-methoxyphenyl)glycidic acid butyl ester | 139345-88-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (2S,3R)-trans-(4-methoxyphenyl)glycidic acid butyl ester
• 英文别名: (2S,3R) trans-3-(4-methoxyphenyl)-glycidic acid butyl ester；butyl (2S,3R)-3-(4-methoxyphenyl)oxirane-2-carboxylate
• CAS: 139345-88-3
• 化学式: C₁₄H₁₈O₄
• 分子量: 250.295
• InChiKey: YAFAQSVHKSGKDB-OLZOCXBDSA-N

物化性质

• 沸点：
  343.3±42.0 °C(Predicted)
• 密度：
  1.139±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  48.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (2R,3S)-rel-3-(4-甲氧基苯基)-2-环氧乙烷羧酸甲酯 、 正丁醇 以 正己烷 为溶剂， 反应 24.0h， 生成 (2S,3R)-trans-(4-methoxyphenyl)glycidic acid butyl ester 、 (2R,3S)-trans-(4-methoxyphenyl)glycidic acid butyl ester
  参考文献：
  名称：

  The enzymic preparation of (2R,3S)-phenyl glycidic acid esters

  摘要：

  DOI：

  10.1021/jo00050a049

文献信息

• Process for preparing optically active trans-3-substituted glycidic acid ester
  申请人：TANABE SEIYAKU CO., LTD.

  公开号：EP0861834A1

  公开（公告）日：1998-09-02

  A process for preparing an optically active trans-3-substituted glycidic acid ester compound of the formula (I): wherein ring A is a substituted or unsubstituted benzene ring, and R1 is an ester residue, which comprises: preparing a solution of one optical isomer (A) and the other optical isomer (B) of the ester compound (I), both of which are the optical isomers due to the asymmetric carbons at 2- and 3-positions, and an ester compound (B') which is different from the isomer (B) only in the ester residue R1, crystallizing the optical isomer (A) from the solution up to the extent that the optical isomer (A) is crystallized without the precipitation of the optical isomer (B) due to the presence of the ester compound (B') though the optical isomer (B) would precipitate if the ester compound (B') were not present, and isolating the crystals of the optical isomer (A), whereby a desired optical isomer (A) can be obtained in high purity and in a high yield such that the desired isomer can be crystallized until the concentration of the desired isomer in the mother liquor becomes very low as compared with conventional processes.

  一种制备具有光学活性的反式-3-取代缩水甘油酸酯类化合物的工艺，其式为 (I)： 其中环 A 是取代或未取代的苯环，R1 是酯残基，它包括 制备酯化合物（I）的一种光学异构体（A）和另一种光学异构体（B）的溶液，这两种光学异构体都是由于 2 位和 3 位上的碳不对称而形成的光学异构体，以及一种酯化合物（B'），该酯化合物（B'）仅在酯残基 R1 上与异构体（B）不同、 从溶液中结晶出光学异构体（A），结晶程度以光学异构体（A）不因酯类化合物（B'）的存在而析出光学异构体（B）为限，尽管如果没有酯类化合物（B'），光学异构体（B）也会析出，以及 分离出光学异构体（A）的晶体，从而获得高纯度和高产率的所需光学异构体（A），使所需异构体可以结晶，直到母液中的所需异构体浓度与传统工艺相比变得非常低。
• A Practical Procedure for the Large-Scale Preparation of Methyl (2<i>R</i>,3<i>S</i>)-3-(4-Methoxyphenyl)glycidate, a Key Intermediate for Diltiazem
  作者：Toshiyuki Furutani、Ritsuo Imashiro、Masanori Hatsuda、Masahiko Seki

  DOI：10.1021/jo025647b

  日期：2002.6.1

  A practical synthesis of methyl (2R,3S)-3-(4-methoxyphenyl)glycidate (-)-2, a key intermediate for diltiazem (1), was developed. Treatment of methyl (E)-4-methoxycinnamate 3 with chiral dioxirane, generated from chiral ketone 4, provided (-)-2 in 77% ee and 89% yield. The crude mixture of (-)-2 and 4 was efficiently separated by the use of novel and simple equipment performing a lipase-catalyzed trans esterification and a continuous dissolution and crystallization to furnish the optically pure (-)-2 and recovery of 4 in 74% and 91% yield, respectively.
• US5998637A
  申请人：——

  公开号：US5998637A

  公开（公告）日：1999-12-07
• US6197953B1
  申请人：——

  公开号：US6197953B1

  公开（公告）日：2001-03-06