3,4-trans-2α-piperonylmethyl-3-hydroxymethyl-4-veratryl-3-buten-1-ol | 126313-83-5

• 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
• 英文名称: 3,4-trans-2α-piperonylmethyl-3-hydroxymethyl-4-veratryl-3-buten-1-ol
• 英文别名: (2R,3E)-2-(1,3-benzodioxol-5-ylmethyl)-3-[(3,4-dimethoxyphenyl)methylidene]butane-1,4-diol
• CAS: 126313-83-5
• 化学式: C₂₁H₂₄O₆
• 分子量: 372.418
• InChiKey: HWKXEOQFCDZEQM-UGIZUQJLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  77.4
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3,4-trans-2α-piperonylmethyl-3-hydroxymethyl-4-veratryl-3-buten-1-ol 生成 Acetic acid (R)-3-acetoxymethyl-4-benzo[1,3]dioxol-5-yl-2-[1-(3,4-dimethoxy-phenyl)-meth-(E)-ylidene]-butyl ester
  参考文献：
  名称：

  GONZALEZ, ANTONIO G.;ESTEVEZ-REYES, RAFAEL;MATO, CARMEN;ESTEVEZ-BRAUN, AN+, PHYTOCHEMISTRY, 29,(1990) N, C. 675-678

  摘要：

  DOI：
• 作为产物：
  描述：

  gossipifan 生成 3,4-trans-2α-piperonylmethyl-3-hydroxymethyl-4-veratryl-3-buten-1-ol
  参考文献：
  名称：

  GONZALEZ, ANTONIO G.;ESTEVEZ-REYES, RAFAEL;MATO, CARMEN;ESTEVEZ-BRAUN, AN+, PHYTOCHEMISTRY, 29,(1990) N, C. 675-678

  摘要：

  DOI：

文献信息

• Synthesis, anti-virus and anti-tumour activities of dibenzylbutyrolactone lignans and their analogues
  作者：Yamu Xia、Jia You、Yuanyuan Zhang、Zhongliang Su

  DOI：10.3184/030823409x12506792542747

  日期：2009.9

  and seven analogues. Four natural lignans were prepared by this method, and five lignans were synthesised for the first time. The synthesised compounds were evaluated for anti-HIV, anti-HSV, and anti-tumour activities. Results showed that the dibenzylbutyrolactone lignans and their analogues were inactive against HIV Tat transactivation and HSV-1 in vitro, but some compounds displayed significant activity

  已开发出二苄基丁内酯木脂素及其类似物的有效合成。基于胡椒醛或藜芦醛与琥珀酸二乙酯的 Stobbe 缩合，以及与 3,4-亚甲基二氧苄基溴的烷基化反应，得到木脂素的骨架。(±)-二酸用奎宁分解并转化官能团以获得三种苄基丁内酯木脂素和七种类似物。采用该方法制备了4种天然木脂素，首次合成了5种木脂素。对合成的化合物进行了抗 HIV、抗 HSV 和抗肿瘤活性的评估。结果表明，二苄基丁内酯木脂素及其类似物在体外对 HIV Tat 反式激活和 HSV-1 无活性，但一些化合物对 MDA-MB-435 人乳腺癌细胞显示出显着的活性。
• Isokaerophyllin, a butyrolactone from Bupleurum salicifolium
  作者：Antonio G. González、Rafael Estévez-Reyes、Carmen Mato、Ana Ma Estévez-Braun

  DOI：10.1016/0031-9422(90)85146-7

  日期：1990.1

  Abstract From the leaves of Bupleurum salicifolium two benzylidene-benzyl-γ-butyrolactone-type lignans were isolated. One was identified as kaerophyllin, the other as its cis-isomer, hitherto unreported. The latter was characterized as 2(3,4-dimethoxy)-benzylidene-3-(3,4-dioxymethyl)-phenylmethyl-3 S-γ-butyrolactone by spectroscopic chemical methods, and from a study of its derivatives.

  摘要 从柴胡叶中分离得到两种苄叉-苄基-γ-丁内酯型木脂素。一种被鉴定为岩藻素，另一种被鉴定为顺式异构体，迄今未见报道。通过光谱化学方法和对其衍生物的研究，后者被表征为 2(3,4-二甲氧基)-苯亚甲基-3-(3,4-二氧甲基)-苯基甲基-3 S-γ-丁内酯。