2,3-双(4-羟基-3-甲氧基苄基)琥珀酸二甲酯 | 190004-70-7

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物 - 二苄基丁烷木脂素
• 中文名称: 2,3-双(4-羟基-3-甲氧基苄基)琥珀酸二甲酯
• 英文名称: dimethyl 2,3-bis-(4-hydroxy-3-methoxybenzyl)succinate
• 英文别名: Dimethyl 2,3-bis[(4-hydroxy-3-methoxyphenyl)methyl]butanedioate
• CAS: 190004-70-7
• 化学式: C₂₂H₂₆O₈
• 分子量: 418.444
• InChiKey: CXEXMGIUNZDVDB-UHFFFAOYSA-N

物化性质

• 沸点：
  587.0±50.0 °C(Predicted)
• 密度：
  1.250±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  30
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  112
• 氢给体数：
  2
• 氢受体数：
  8

上下游信息

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  3,4-二香草基四氢呋喃	4-({4-[(4-hydroxy-3-methoxyphenyl)methyl]oxolan-3-yl}methyl)-2-methoxyphenol	34730-78-4	C20H24O5	344.408
  2,3-双[(4-羟基-3-甲氧基苯基)甲基]丁烷-1,4-二醇	(+/-)-secoisolariciresinol	29388-59-8	C20H26O6	362.423
  (+)-开环异落叶松树脂酚	(-)-secoisolariciresinol	145265-02-7	C20H26O6	362.423
  9,9'-二-O-(E)-阿魏酰开环异落叶松脂素	(-)-(2R,3R)-1,4-O-diferuloylsecoisolariciresinol	56973-66-1	C40H42O12	714.766

反应信息

• 作为反应物：
  描述：

  2,3-双(4-羟基-3-甲氧基苄基)琥珀酸二甲酯 在 lithium aluminium tetrahydride 作用下， 生成 2,3-双[(4-羟基-3-甲氧基苯基)甲基]丁烷-1,4-二醇
  参考文献：
  名称：

  柿子的花萼木脂素

  摘要：

  摘要 从柿子萼中分离到了一种新的木脂素。其结构通过光谱方法阐明为 (-)-二乙烯基四氢呋喃阿魏酸酯，并通过全合成确定。

  DOI：

  10.1016/s0031-9422(00)80791-8
• 作为产物：
  描述：

  Dimethyl 2,3-bis[(3-methoxy-4-phenylmethoxyphenyl)methyl]butanedioate 以8 g的产率得到2,3-双(4-羟基-3-甲氧基苄基)琥珀酸二甲酯
  参考文献：
  名称：

  柿子的花萼木脂素

  摘要：

  摘要 从柿子萼中分离到了一种新的木脂素。其结构通过光谱方法阐明为 (-)-二乙烯基四氢呋喃阿魏酸酯，并通过全合成确定。

  DOI：

  10.1016/s0031-9422(00)80791-8

文献信息

• Synthesis and evaluation of cytotoxic effects of hanultarin and its derivatives
  作者：Eunyoung Lee、V.S. Jamal Ahamed、Mahto Sanjeev Kumar、Seog Woo Rhee、Surk-Sik Moon、In Seok Hong

  DOI：10.1016/j.bmcl.2011.09.014

  日期：2011.11

  One of the known cytotoxic lignans is (-)-1-O-feruloyl-secoisolariciresinol designated as hanultarin, which was isolated from the seeds of Trichosanthes kirilowii. In this Letter, we described the first synthesis of 1-O-feruloyl-secoisolariciresinol, 1,4-O-diferuloyl-secoisolariceresinol and their analogues. The cytotoxicities of these compounds were evaluated against several cancer cell lines. Interestingly, we found that the feruloyl diester derivative of secoisolariciresinol was the most active cytotoxic compound against all the cancer cells tested in this experiment. The IC(50) values of the 1,4-O-diferuloyl-secoisolariceresinol were in the range of 7.1-9.8 mu M except one cell line. In considering that both ferulic acid and secoisolariciresinol are commonly found in many plants and have no cytotoxicity, this finding is remarkable in that simple covalent bonds between the ferulic acid and secoisolariciresinol cause a cytotoxic effect. (C) 2011 Elsevier Ltd. All rights reserved.
• Bioorg. Med. Chem. Lett. 2013, 23, 5325-5328
  作者：

  DOI：——

  日期：——
• Lignan from calyces of Diospyros kaki
  作者：Shin Matsuura、Munekazu Iinuma

  DOI：10.1016/s0031-9422(00)80791-8

  日期：——

  Abstract From Diospyros kaki calyces, a new lignan was isolated. Its structure was elucidated as (−)-divanillyltetrahydrofuran ferulate by spectroscopic methods and was established by total synthesis.

  摘要 从柿子萼中分离到了一种新的木脂素。其结构通过光谱方法阐明为 (-)-二乙烯基四氢呋喃阿魏酸酯，并通过全合成确定。