methyl (E)-4-methoxymethyl-3-methoxycinnamate | 220300-07-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: methyl (E)-4-methoxymethyl-3-methoxycinnamate
• CAS: 220300-07-2
• 化学式: C₁₃H₁₆O₅
• 分子量: 252.267
• InChiKey: KSVWXRKXICLUHW-FNORWQNLSA-N

物化性质

• 沸点：
  376.6±37.0 °C(Predicted)
• 密度：
  1.140±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.86
• 重原子数：
  18.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  53.99
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  methyl (E)-4-methoxymethyl-3-methoxycinnamate 在 盐酸 作用下， 以 甲醇 为溶剂， 反应 0.5h， 以100%的产率得到阿魏酸甲酯
  参考文献：
  名称：

  Facile one-pot transformation of 2,3-epoxy alcohols into allylic alcohols: first total synthesis of (−)-4-O-(6′-hydroxy-7′(9′)-dehydro-6′,7′-dihydrogeranyl)coniferol

  摘要：

  An efficient and practical synthesis of optically active allylic alcohols from 2,3-epoxy alcohols by the in situ formation of the epoxy iodides and their subsequent reduction with phosphine hydroxyiodide has been established. Using this reaction as the key step, we synthesized (-)-4-O-(6'-hydroxy-7'(9')-dehydro-6',7'-dihydrogeranyl)coniferol. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(98)00385-1
• 作为产物：
  描述：

  香草醛 在 哌啶 、 吡啶 、 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 8.0h， 生成 methyl (E)-4-methoxymethyl-3-methoxycinnamate
  参考文献：
  名称：

  First total synthesis of Boehmenan

  摘要：

  已成功实现了二氢木脂素Boehmenan的首次全合成。在氧化银存在下，阿魏酸甲酯的仿生氧化耦合是合成序列中的关键步骤，生成了二氢苯并呋喃骨架。羟基被DHP保护，并用LiAlH4还原，得到中间二醇。该二醇与阿魏酸衍生物缩合，然后去除保护基团，获得Boehmenan。同时，还描述了在碱性条件下中间二氢苯并呋喃新木脂素的环开反应研究。

  DOI：

  10.1007/s12039-014-0599-7

文献信息

• Total synthesis of (±)-divanillyltetrahydrofuran ferulate
  作者：Ya-Mu Xia、Jia You、Qi Wang

  DOI：10.1007/s12039-010-0050-7

  日期：2010.5

  A convenient method for the synthesis of sesquilignan threo- and erythro-(±)-divanillyltetrahydrofuran ferulate is described. The synthesis was based on a unified synthetic strategy involving two Stobbe condensations to give the skeleton of lignan, and then reduction reaction to form meso- and threo-(±)-secoisolanciresinol. meso- and threo-(±)-secoisolanciresinol were separated by flash column chromatography

  描述了一种合成芝麻基苏木和苏式-（±）-二香草基四氢呋喃阿魏酸酯的简便方法。合成基于统一的合成策略，该策略涉及两次Stobbe缩合以生成木脂素的骨架，然后进行还原反应以形成内消旋和苏-异（±）-异二十二碳五烯醇。内消旋-和苏式- （±）-secoisolanciresinol通过快速柱色谱法分离，通过用分子内的TsCl反应，得到关键中间体，随后内消旋-或苏-与阿魏酸（±）-shonanin，然后缩合以获得sesquilignan苏-或其类似物赤型-（±）-二香草基四氢呋喃阿魏酸酯。
• Facile one-pot transformation of 2,3-epoxy alcohols into allylic alcohols: first total synthesis of (−)-4-O-(6′-hydroxy-7′(9′)-dehydro-6′,7′-dihydrogeranyl)coniferol
  作者：Zuosheng Liu、Jiong Lan、Yulin Li

  DOI：10.1016/s0957-4166(98)00385-1

  日期：1998.11

  An efficient and practical synthesis of optically active allylic alcohols from 2,3-epoxy alcohols by the in situ formation of the epoxy iodides and their subsequent reduction with phosphine hydroxyiodide has been established. Using this reaction as the key step, we synthesized (-)-4-O-(6'-hydroxy-7'(9')-dehydro-6',7'-dihydrogeranyl)coniferol. (C) 1998 Elsevier Science Ltd. All rights reserved.
• First total synthesis of Boehmenan
  作者：YAMU XIA、XIAOLI DAI、HAIXIN LIU、CHEN CHAI

  DOI：10.1007/s12039-014-0599-7

  日期：2014.5

  The first total synthesis of dilignan Boehmenan has been achieved. A biomimetic oxidative coupling of the ferulic acid methyl ester in the presence of silver oxide is the crucial step in the synthesis sequence, generating the dihydrobenzofuran skeleton. Hydroxyl group was protected with DHP and reducted with LiAlH 4 to afford the intermediate diol. The diol was condensated with the derivative of ferulic acid, then removed the protecting groups, to get Boehmenan. Meanwhile, a study on the ring-opening reaction of the intermediate dihydrobenzofuran neolignan under base conditions was described.

  已成功实现了二氢木脂素Boehmenan的首次全合成。在氧化银存在下，阿魏酸甲酯的仿生氧化耦合是合成序列中的关键步骤，生成了二氢苯并呋喃骨架。羟基被DHP保护，并用LiAlH4还原，得到中间二醇。该二醇与阿魏酸衍生物缩合，然后去除保护基团，获得Boehmenan。同时，还描述了在碱性条件下中间二氢苯并呋喃新木脂素的环开反应研究。