cassiarin B

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: cassiarin B
• 英文别名: methyl 4-(3,7-dimethyl-11-oxo-2-oxa-6-azatricyclo[7.3.1.05,13]trideca-1(12),3,5(13),7,9-pentaen-6-yl)butanoate
• 化学式: C₁₈H₁₉NO₄
• 分子量: 313.353
• InChiKey: OTLORQJLOJHVHW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  N-(4-methoxy-4-oxobutyl)cassiarin A chloride 在 sodium carbonate 作用下， 以 水 为溶剂， 反应 0.08h， 以60%的产率得到cassiarin B
  参考文献：
  名称：

  Transformation of barakol into cassiarins A, B, and their derivatives

  摘要：

  Three semi-syntheses of cassiarins A and B from barakol are described. The route involving use of anhydrobarakol chloride as a key precursor showed most versatility because it does not require an expensive catalyst, protection of functional groups, or chromatographic purification, allowing the facile preparation of eight cassiarin derivatives. The photophysical properties of these compounds were characterized by UV-vis absorption, fluorescence emission, and quantum yield. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.07.053

文献信息

• Biomimetic Total Syntheses of Cassiarins A and B
  作者：Yuan-Shan Yao、Zhu-Jun Yao

  DOI：10.1021/jo801017b

  日期：2008.7.1

  Total syntheses of cassiarins A and B have been efficiently accomplished using a common strategy with biomimetic considerations. Key reactions involved in this synthesis include a Negishi-type coupling, a Ag(I)-promoted formation of the tricyclic 8H-pyrano[2,3,4-de]chromen-8-one core, and a sequential amine-condensation and cyclization. Three new analogues of cassiarin A bearing different substituents

  使用仿生学的通用策略已有效地完成了卡西林A和B的总合成。参与该合成的关键反应包括Negishi型偶联，Ag（I）促进的三环8 H-吡喃并[2,3,4- de ] chromen -8-one核的形成以及顺序的胺缩合和环化。从同一中间体平行合成了三个新的肉桂素A类似物，它们在C-11位置带有不同的取代基。另外，从相应的化学等效前体获得了对关键三环核心和卡西林A和B的另外两个转化。
• Isolation and biological evaluation of demethylcassiarin B from <i>Senna siamea</i> Lam.
  作者：Rohini Verma、S.M. Jachak

  DOI：10.1080/14786419.2023.2165075

  日期：——

  In search of potential natural products for the amelioration of obesity, phytochemical investigation of leaves of Senna siamea Lam. was carried out. It led to the isolation of demethycassiarin B (1...

  为了寻找改善肥胖的潜在天然产物，对番泻叶叶进行植物化学研究。进行了。它导致了 demethycassiarin B (1...
• Transformation of barakol into cassiarins A, B, and their derivatives
  作者：Sarawut Kanputhorn、Amorn Petsom、Patchanita Thamyongkit

  DOI：10.1016/j.tet.2010.07.053

  日期：2010.9

  Three semi-syntheses of cassiarins A and B from barakol are described. The route involving use of anhydrobarakol chloride as a key precursor showed most versatility because it does not require an expensive catalyst, protection of functional groups, or chromatographic purification, allowing the facile preparation of eight cassiarin derivatives. The photophysical properties of these compounds were characterized by UV-vis absorption, fluorescence emission, and quantum yield. (C) 2010 Elsevier Ltd. All rights reserved.