2'-O-methylvestitol | 41743-86-6

• 物质功能分类: 天然产物 - 黄酮类化合物
• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 异黄酮类化合物
• 英文名称: 2'-O-methylvestitol
• 英文别名: sativan；3-(2,4-dimethoxyphenyl)-chroman-7-ol；rac-sativan；(±)-sativan；3-(2,4-dimethoxyphenyl)-3,4-dihydro-2H-chromen-7-ol
• CAS: 41743-86-6
• 化学式: C₁₇H₁₈O₄
• 分子量: 286.328
• InChiKey: TUXCLJQCYVCGDW-UHFFFAOYSA-N

物化性质

• 熔点：
  125-127 °C
• 沸点：
  443.6±45.0 °C(Predicted)
• 密度：
  1.203±0.06 g/cm3(Predicted)
• 物理描述：
  Solid
• 保留指数：
  2687.9

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  47.9
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 海关编码：
  2932999099

反应信息

• 作为反应物：
  描述：

  2'-O-methylvestitol 在 三溴化硼 、 溶剂黄146 、 苯硼酸 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 14.0h， 生成 glabridin
  参考文献：
  名称：

  Total Synthesis of (±)-Glabridin

  摘要：

  An efficient formal synthesis of (+/-)-glabridin was accomplished in 10 steps from resorcinol using Raney Ni to reduce carbon-carbon double bonds in alpha,beta-unsaturated carbonyl compound as the key step. [Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications (R) for the following free supplemental resource(s): Full experimental and spectral details.]

  DOI：

  10.1080/00397911.2013.821616
• 作为产物：
  描述：

  2,4-二甲氧基苯乙酮 在 吗啉 、 5%-palladium/activated carbon 、 三氟化硼乙醚 、 氢气 、 sulfur 、 溶剂黄146 作用下， 以 乙醇 、 水 为溶剂， 反应 39.5h， 生成 2'-O-methylvestitol
  参考文献：
  名称：

  Total Synthesis of (±)-Glabridin

  摘要：

  An efficient formal synthesis of (+/-)-glabridin was accomplished in 10 steps from resorcinol using Raney Ni to reduce carbon-carbon double bonds in alpha,beta-unsaturated carbonyl compound as the key step. [Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications (R) for the following free supplemental resource(s): Full experimental and spectral details.]

  DOI：

  10.1080/00397911.2013.821616

文献信息

• A step-economical divergent approach to isoflavenes based on Suzuki–Miyaura cross coupling of a 3-boryl-2<i>H</i>-chromene with aryl bromides: application to total synthesis of isoflavonoid natural products
  作者：Yuichiro Uchida、Hirosato Takikawa、Bubwoong Kang

  DOI：10.1093/bbb/zbad076

  日期：2023.8.23

  coupling of a 3-boryl-2H-chromene and three aryl bromides. 3-Boryl-2H-chromene, which is not a well-explored species, was prepared via Miyaura-Ishiyama borylation of a 3-chloro-2H-chromene obtained through a Claisen rearrangement cyclization cascade reaction. Further conversion of the cross-coupling products, three isoflavene derivatives, afforded three isoflavonoid natural products with one or two additional

  我们提出了一种使用 3-硼基-2H-色烯和三个芳基溴化物的 Suzuki-Miyaura 交叉偶联来合成异黄烯衍生物的经济的分步合成方法。3-硼基-2H-色烯不是一个被充分探索的物种，它是通过克莱森重排环化级联反应获得的 3-氯-2H-色烯通过 Miyaura-Ishiyama 硼酸化制备的。交叉偶联产物（三种异黄烯衍生物）的进一步转化通过一两个额外的反应步骤提供了三种异黄酮天然产物。
• Total Synthesis of (±)-Glabridin
  作者：Wen-Hua Ji、Qian-Shan Gao、Yun-Liang Lin、Hong-Mei Gao、Xiao Wang、Yan-Ling Geng

  DOI：10.1080/00397911.2013.821616

  日期：2014.2.16

  An efficient formal synthesis of (+/-)-glabridin was accomplished in 10 steps from resorcinol using Raney Ni to reduce carbon-carbon double bonds in alpha,beta-unsaturated carbonyl compound as the key step. [Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications (R) for the following free supplemental resource(s): Full experimental and spectral details.]