19-furan-2-ylnonadeca-5,7-diynoic acid | 874163-29-8

• 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: 19-furan-2-ylnonadeca-5,7-diynoic acid
• 英文别名: 19-(2-Furyl)nonadeca-5,7-diynoic acid；19-(furan-2-yl)nonadeca-5,7-diynoic acid
• CAS: 874163-29-8
• 化学式: C₂₃H₃₂O₃
• 分子量: 356.505
• InChiKey: AZDANMRNWNLXOP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  26
• 可旋转键数：
  15
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  50.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  甲醇 、 19-furan-2-ylnonadeca-5,7-diynoic acid 在 氯化亚砜 作用下， 反应 15.0h， 以65%的产率得到19-furan-2-ylnonadeca-5,7-diynoic acid methyl ester
  参考文献：
  名称：

  Synthesis of Natural Polyacetylenes Bearing Furan Rings

  摘要：

  The first total syntheses of four new polyacetylene compounds have been achieved using convergent routes, which involved Cadiot-Chodkiewicz copper-catalyzed cross-coupling reactions to sp-sp centers as the key steps. 19-Furan-2-ylnonadeca-5,7-diynoic acid (1), 19-furan-2-ylnonadeca-5,7-diynoic acid methyl ester (2), 2-pentacosa-7,9-diynylfuran (3), and 21-furan-2-ylhenicosa-14,16-diyn-1-ol (4) were stable and could be readily identified, isolated, and purified in high overall yields.

  DOI：

  10.1021/np9000637
• 作为产物：
  描述：

  19-furan-2-ylnonadeca-5,7-diynol 在 重铬酸吡啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 以49%的产率得到19-furan-2-ylnonadeca-5,7-diynoic acid
  参考文献：
  名称：

  Synthesis of Natural Polyacetylenes Bearing Furan Rings

  摘要：

  The first total syntheses of four new polyacetylene compounds have been achieved using convergent routes, which involved Cadiot-Chodkiewicz copper-catalyzed cross-coupling reactions to sp-sp centers as the key steps. 19-Furan-2-ylnonadeca-5,7-diynoic acid (1), 19-furan-2-ylnonadeca-5,7-diynoic acid methyl ester (2), 2-pentacosa-7,9-diynylfuran (3), and 21-furan-2-ylhenicosa-14,16-diyn-1-ol (4) were stable and could be readily identified, isolated, and purified in high overall yields.

  DOI：

  10.1021/np9000637

文献信息

• 2-Substituted Furans from the Roots of <i>Polyalthia evecta</i>
  作者：Somdej Kanokmedhakul、Kwanjai Kanokmedhakul、Itsara Kantikeaw、Nutchanat Phonkerd

  DOI：10.1021/np0503202

  日期：2006.1.1

  Four new 2-substituted furans, 19-(2-furyl)nonadeca-5,7-diynoic acid (1), 19-(2-furyl)nonadeca-5-ynoic acid (2), 1-(2-furyl)-pentacosa-7,9-diyne (3), and ester 21-(2-furyl)heneicosa-14,16-diyne-19-(2-furyl)nonadeca-5,7-diynoate (4) have been isolated from the roots of Polyalthia evecta. Their structures were established by spectroscopic techniques. Compounds 1 and 1a showed antiplasmodial activity. The acids I and 2 exhibited antiviral activity against Herpes simplex type 1. In addition, 5 also showed cytotoxicity against the NCI-H187 cell line.
• Synthesis of Natural Polyacetylenes Bearing Furan Rings
  作者：Daniela A. Barancelli、Anderson C. Mantovani、Cristiano Jesse、Cristina W. Nogueira、Gilson Zeni

  DOI：10.1021/np9000637

  日期：2009.5.22

  The first total syntheses of four new polyacetylene compounds have been achieved using convergent routes, which involved Cadiot-Chodkiewicz copper-catalyzed cross-coupling reactions to sp-sp centers as the key steps. 19-Furan-2-ylnonadeca-5,7-diynoic acid (1), 19-furan-2-ylnonadeca-5,7-diynoic acid methyl ester (2), 2-pentacosa-7,9-diynylfuran (3), and 21-furan-2-ylhenicosa-14,16-diyn-1-ol (4) were stable and could be readily identified, isolated, and purified in high overall yields.

表征谱图