cajanolactone A | 1421341-46-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 异香豆素及其衍生物
• 英文名称: cajanolactone A
• 英文别名: 8-Hydroxy-6-methoxy-5-(3-methylbut-2-enyl)-3-phenylisochromen-1-one；8-hydroxy-6-methoxy-5-(3-methylbut-2-enyl)-3-phenylisochromen-1-one
• CAS: 1421341-46-9
• 化学式: C₂₁H₂₀O₄
• 分子量: 336.387
• InChiKey: JCWMYWSAQHRMAA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  cajanolactone A 在 水 、 potassium hydroxide 作用下， 以 乙醇 为溶剂， 反应 8.0h， 以82%的产率得到cajanonic acid A
  参考文献：
  名称：

  First total synthesis of natural products cajanolactone A and cajanonic acid A

  摘要：

  First total synthesis of cajanolactone A and cajanonic acid A has been achieved through steps of anion-anion condensations, cyclization, Williams etherification, selective demethylation, 1,3-sigmatropic rearrangement and hydrolysis. This work provides an efficient method for future cajanonic acid A derivatives synthesis. (C) 2014 Lei Tang. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.

  DOI：

  10.1016/j.cclet.2014.03.027
• 作为产物：
  描述：

  N-甲基-N-甲基苯甲酰胺 在 aluminum (III) chloride 、 potassium carbonate 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.42h， 生成 cajanolactone A
  参考文献：
  名称：

  First total synthesis of natural products cajanolactone A and cajanonic acid A

  摘要：

  First total synthesis of cajanolactone A and cajanonic acid A has been achieved through steps of anion-anion condensations, cyclization, Williams etherification, selective demethylation, 1,3-sigmatropic rearrangement and hydrolysis. This work provides an efficient method for future cajanonic acid A derivatives synthesis. (C) 2014 Lei Tang. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.

  DOI：

  10.1016/j.cclet.2014.03.027

文献信息

• Synthesis of 3-Arylisocoumarins by Using Acyl Anion Chemistry and Synthesis of Thunberginol A and Cajanolactone A
  作者：Kasireddy Sudarshan、Manash Kumar Manna、Indrapal Singh Aidhen

  DOI：10.1002/ejoc.201403524

  日期：2015.3

  new strategy for the synthesis of 3-arylisocoumarins and 8-hydroxy-3-arylisocoumarins was investigated by using acyl anion chemistry for the initial C–C bond formation. The obtained keto esters and keto lactones as intermediates underwent based-promoted intramolecular cyclization to afford 3-arylisocoumarins in good yields. The developed methodology was applied for the synthesis of the important natural

  3-芳基异香豆素和8-羟基-3-芳基异香豆素的合成新策略通过使用酰基阴离子化学进行初始C-C键形成研究。得到的酮酯和酮内酯作为中间体进行基于促进的分子内环化，以良好的产率得到3-芳基异香豆素。所开发的方法用于合成重要的天然产物 thunberginol A 和 cajanolactone A。
• First total synthesis of natural products cajanolactone A and cajanonic acid A
  作者：Wen-Zhang Chen、Ling-Ling Fan、Hai-Tao Xiao、Ying Zhou、Wan Xiao、Jian-Ta Wang、Lei Tang

  DOI：10.1016/j.cclet.2014.03.027

  日期：2014.5

  First total synthesis of cajanolactone A and cajanonic acid A has been achieved through steps of anion-anion condensations, cyclization, Williams etherification, selective demethylation, 1,3-sigmatropic rearrangement and hydrolysis. This work provides an efficient method for future cajanonic acid A derivatives synthesis. (C) 2014 Lei Tang. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.