(2Z,7Z)-14-(2-oxacyclohexyl)oxypentadeca-2,7-dien-4-yne | 1042439-78-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: (2Z,7Z)-14-(2-oxacyclohexyl)oxypentadeca-2,7-dien-4-yne
• 英文别名: 2-[(8Z,13Z)-pentadeca-8,13-dien-11-yn-2-yl]oxyoxane
• CAS: 1042439-78-0
• 化学式: C₂₀H₃₂O₂
• 分子量: 304.473
• InChiKey: LDWMTMWSLSQOHT-JYKTZQBOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  22
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2Z,7Z)-14-(2-oxacyclohexyl)oxypentadeca-2,7-dien-4-yne 在 甲醇 、 4-甲基苯磺酸吡啶 作用下， 反应 1.0h， 以100%的产率得到(8Z,13Z)-pentadeca-8,13-dien-11-yn-2-ol
  参考文献：
  名称：

  Total synthesis of a dienynone from Echinacea pallida

  摘要：

  The first total synthesis of (8Z,13Z)-pentadeca-8,13-dien-11-yn-2-one is described. This dienynone was recently isolated from the n-hexane extract of Echinacea pallida roots and displayed a selective cytotoxic activity toward cancer cells, thus featuring as a potential anticancer lead. The product was obtained in 11 steps in 25% overall yield. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.04.094
• 作为产物：
  描述：

  顺式-1-溴-1-丙烯 、 (4Z)-11-(2-oxacyclohexyloxy)dodec-4-en-1-yne 在 四(三苯基膦)钯 哌啶 作用下， 以96%的产率得到(2Z,7Z)-14-(2-oxacyclohexyl)oxypentadeca-2,7-dien-4-yne
  参考文献：
  名称：

  Total synthesis of a dienynone from Echinacea pallida

  摘要：

  The first total synthesis of (8Z,13Z)-pentadeca-8,13-dien-11-yn-2-one is described. This dienynone was recently isolated from the n-hexane extract of Echinacea pallida roots and displayed a selective cytotoxic activity toward cancer cells, thus featuring as a potential anticancer lead. The product was obtained in 11 steps in 25% overall yield. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.04.094

文献信息

• Total synthesis of a dienynone from Echinacea pallida
  作者：Stefania Morandi、Federica Pellati、Stefania Benvenuti、Fabio Prati

  DOI：10.1016/j.tet.2008.04.094

  日期：2008.6

  The first total synthesis of (8Z,13Z)-pentadeca-8,13-dien-11-yn-2-one is described. This dienynone was recently isolated from the n-hexane extract of Echinacea pallida roots and displayed a selective cytotoxic activity toward cancer cells, thus featuring as a potential anticancer lead. The product was obtained in 11 steps in 25% overall yield. (C) 2008 Elsevier Ltd. All rights reserved.