methyl 2-hydroxy-3-methoxy-3-(4-methyoxyphenyl)propionate | 97652-92-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: methyl 2-hydroxy-3-methoxy-3-(4-methyoxyphenyl)propionate
• 英文别名: Methyl 2-hydroxy-3-methoxy-3-(4-methoxyphenyl)propanoate
• CAS: 97652-92-1
• 化学式: C₁₂H₁₆O₅
• 分子量: 240.256
• InChiKey: ZHWOMTKOAZQMJG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

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 、 sodium o-nitrophenate 以20%的产率得到
  参考文献：
  名称：

  HASHIYAMA, TOMIKI;WATANABE, AKISHIGE;INOUE, HIROZUMI;KONDA, MIKIHIKO;TAKE+, CHEM. AND PHARM. BULL., 1985, 33, N 2, 634-641

  摘要：

  DOI：

文献信息

• Reaction of 3-phenylglycidic esters. IV. Reaction of methyl 3-(4-methoxyphenyl)glycidate with 2-nitrophenol and synthesis of 1,5-benzoxazepine derivatives.
  作者：TOMIKI HASHIYAMA、AKISHIGE WATANABE、HIROZUMI INOUE、MIKIHIKO KONDA、MIKIO TAKEDA、SAKAE MURATA、TAKU NAGAO

  DOI：10.1248/cpb.33.634

  日期：——

  The reaction of methyl trans-3-(4-methoxyphenyl) glycidate (1) with 2-nitrophenol was investigated under various conditions. Generally, the reaction proceeded predominantly by cis-opening of the oxirane ring of 1 to give the threo-nitro ester (7). Selective trans-opening of 1 was observed only in the reaction with sodium 2-nitrophenoxide to give the erythro-nitro ester (8). Some 1, 5-benzoxazepine derivatives (16-19), 1-oxa analogues of diltiazem, were synthesized from 7 and 8 for pharmacological evaluation. Compound 18a showed the highest vasodilating activity in this series, but it was less active and more toxic than racemic diltiazem.

  研究人员在不同条件下考察了反式-3-（4-甲氧基苯基）甘氨酸甲酯（1）与 2-硝基苯酚的反应。一般来说，反应主要通过 1 的环氧乙烷环顺式开环进行，生成三硝基酯（7）。只有在与 2-硝基苯氧化钠反应生成赤藓硝基酯时，才观察到 1 的选择性反式开环（8）。从 7 和 8 合成了一些 1，5-苯并氧氮杂卓衍生物（16-19），即地尔硫卓的 1-oxa 类似物，用于药理评估。化合物 18a 在该系列中显示出最高的血管扩张活性，但其活性和毒性均低于外消旋地尔硫卓。
• Hydrazine sulphate: a cheap and efficient catalyst for the regioselective ring-opening of epoxides. A metal-free procedure for the preparation of β-alkoxy alcohols
  作者：Alcino J.L. Leitão、Jorge A.R. Salvador、Rui M.A. Pinto、M. Luísa Sá e Melo

  DOI：10.1016/j.tetlet.2007.12.121

  日期：2008.3

  An efficient and general procedure for the regioselective ring opening of epoxides with alcohols to afford the corresponding beta-alkoxy alcohols, using hydrazine sulphate as catalyst, is described. This new metal-free process was found to be highly versatile allowing the use of primary, secondary and tertiary alcohols as nucleophiles and a large variety of epoxides, including 5 alpha,6 alpha-, 5 beta,6 beta- and 2 alpha,3 alpha-epoxysteroids, as substrates. (c) 2008 Elsevier Ltd. All rights reserved.