falcarindiol

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: falcarindiol
• 英文别名: (3S,8R,Z)-Heptadeca-1,9-dien-4,6-diyne-3,8-diol；(3S,8R,9Z)-heptadeca-1,9-dien-4,6-diyne-3,8-diol
• 化学式: C₁₇H₂₄O₂
• 分子量: 260.376
• InChiKey: QWCNQXNAFCBLLV-OQDIJTRPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  19
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 生成 falcarindiol
  参考文献：
  名称：

  Establishment of absolute stereostructure of falcarindiol, algicidal principle against Heterocapsa circularisquama from Notopterygii Rhizoma

  摘要：

  Falcarindiol (1) was isolated as an algicidal principle against the harmful red tide dinoflagellate, Heterocapsa circularisquama, from Notopterygii Rhizoma through bioassay-guided separation. In order to determine the ambiguous absolute structure of this active principle, all three stereoisomers as well as falcarindiol (1) were synthesized. As a result of intensive analysis of their physicochemical properties, the configuration of I was revealed to be 3R,8S. On the other hand, (3S,8S)- and (3S,8R)-isomers were found to exhibit more potent algicidal activity than (3R,8S)-falcarindiol (1) isolated from Notopterygii Rhizoma. In addition, the diyne moiety of 1 was established as the crucial structural requirement for algicidal potency. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.01.047

文献信息

• Establishment of absolute stereostructure of falcarindiol, algicidal principle against Heterocapsa circularisquama from Notopterygii Rhizoma
  作者：Satoru Tamura、Tomomichi Ohno、Yuuhi Hattori、Nobutoshi Murakami

  DOI：10.1016/j.tetlet.2010.01.047

  日期：2010.3

  Falcarindiol (1) was isolated as an algicidal principle against the harmful red tide dinoflagellate, Heterocapsa circularisquama, from Notopterygii Rhizoma through bioassay-guided separation. In order to determine the ambiguous absolute structure of this active principle, all three stereoisomers as well as falcarindiol (1) were synthesized. As a result of intensive analysis of their physicochemical properties, the configuration of I was revealed to be 3R,8S. On the other hand, (3S,8S)- and (3S,8R)-isomers were found to exhibit more potent algicidal activity than (3R,8S)-falcarindiol (1) isolated from Notopterygii Rhizoma. In addition, the diyne moiety of 1 was established as the crucial structural requirement for algicidal potency. (C) 2010 Elsevier Ltd. All rights reserved.