(Z)-3,7-dimethyl-1-(prop-2-yn-1-yloxy)octa-2,6-diene | 33470-50-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (Z)-3,7-dimethyl-1-(prop-2-yn-1-yloxy)octa-2,6-diene
• 英文别名: (2Z)-3,7-dimethyl-1-prop-2-ynoxyocta-2,6-diene
• CAS: 33470-50-7
• 化学式: C₁₃H₂₀O
• 分子量: 192.301
• InChiKey: NZWRILVCJIAXRF-LCYFTJDESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  14
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (Z)-3,7-dimethyl-1-(prop-2-yn-1-yloxy)octa-2,6-diene 、 1-(叠氮甲基)-4-溴苯 在 copper(ll) sulfate pentahydrate 、 sodium ascorbate 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 24.0h， 以67%的产率得到(Z)-1-(4-bromobenzyl)-4-(((3,7-dimethylocta-2,6-dien-1-yl)oxy)methyl)-1H-1,2,3-triazole
  参考文献：
  名称：

  Synthesis of Nerol Derivatives Containing a 1,2,3-Triazole Moiety and Evaluation of Their Activities against Cancer Cell Lines

  摘要：

  In the present investigation, a collection of twenty two nerol derivatives, containing 1,2,3-triazolic appendages, was synthesized and screened in vitro for their cytotoxic activity against HL60, Nalm6, and Jurkat human leukemia cells as well as against B16F10 (melanoma cell line). In most cases, derivatives were able to reduce cell viability. The most potent compound (Z)-4-(((3,7-dimethylocta-2,6-dien-1-yl)oxy)methyl)-1-(4-(trifluoromethoxy)benzyl)1H-1,2,3 triazole showed antiproliferative activity against Jurkat cells and reduced B16F10 cell migration. Physicochemical properties of the compounds were calculated in order to evaluate their potential for drug development. Most of the evaluated physicochemical parameters seemed to be favorable for drug development. In addition, for a better understanding of the biological activity results, 3D quantitative structure-activity relationship (QSAR) studies were carried out. 3D-QSAR studies indicate that the anticancer activities observed for the cell lines HL60 and Jurkat may occur by a similar mechanism of action and the same was found for the Nalm6 and B16F10 cell lines.

  DOI：

  10.21577/0103-5053.20180203
• 作为产物：
  描述：

  橙花醇 、 3-溴丙炔 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 22.0h， 以97%的产率得到(Z)-3,7-dimethyl-1-(prop-2-yn-1-yloxy)octa-2,6-diene
  参考文献：
  名称：

  Synthesis of Nerol Derivatives Containing a 1,2,3-Triazole Moiety and Evaluation of Their Activities against Cancer Cell Lines

  摘要：

  In the present investigation, a collection of twenty two nerol derivatives, containing 1,2,3-triazolic appendages, was synthesized and screened in vitro for their cytotoxic activity against HL60, Nalm6, and Jurkat human leukemia cells as well as against B16F10 (melanoma cell line). In most cases, derivatives were able to reduce cell viability. The most potent compound (Z)-4-(((3,7-dimethylocta-2,6-dien-1-yl)oxy)methyl)-1-(4-(trifluoromethoxy)benzyl)1H-1,2,3 triazole showed antiproliferative activity against Jurkat cells and reduced B16F10 cell migration. Physicochemical properties of the compounds were calculated in order to evaluate their potential for drug development. Most of the evaluated physicochemical parameters seemed to be favorable for drug development. In addition, for a better understanding of the biological activity results, 3D quantitative structure-activity relationship (QSAR) studies were carried out. 3D-QSAR studies indicate that the anticancer activities observed for the cell lines HL60 and Jurkat may occur by a similar mechanism of action and the same was found for the Nalm6 and B16F10 cell lines.

  DOI：

  10.21577/0103-5053.20180203

文献信息

• Highly catalyst-dependent cycloisomerisation of an O-tethered enyne derived from nerol
  作者：Ariadna Fuente-Hernandez、Philippe Costes、Philippe Kalck、José A. Ruiz-García、Ulises Jáuregui-Haza、Martine Urrutigoïty、Odile Dechy-Cabaret

  DOI：10.1016/j.catcom.2010.08.019

  日期：2010.11

  The cycloisomerisation of an O-tethered enyne derived from nerol has been studied using various catalytic systems such as PtCl(2) AuCl(3) [AuCl(PPh(3))]/AgPF(6)} and [Rh(2)Cl(2)(CO)(4)] Whatever the catalyst used formal Alder-ene 1 4-dienes were obtained as major products along with cyclopropane and 13 diene derivatives indicating the crucial influence of the structure of the enyne substrate on the course of the reaction Differences in terms of activity and selectivity nevertheless appeared when moving from Rh- or Pt-based catalysts to Au(I)-based catalysts mechanistic pathways are proposed to explain these observations (C) 2010 Elsevier B V All rights reserved
• Synthesis of Nerol Derivatives Containing a 1,2,3-Triazole Moiety and Evaluation of Their Activities against Cancer Cell Lines
  作者：Róbson Teixeira、Adalberto da Silva、Raoni Siqueira、Victor Hugo Gonçalves、Higor Pereira、Rafaela Ferreira、Adilson Costa、Eduardo de Melo、Fávero Paula、Márcia Ferreira、Gustavo Bressan

  DOI：10.21577/0103-5053.20180203

  日期：——

  In the present investigation, a collection of twenty two nerol derivatives, containing 1,2,3-triazolic appendages, was synthesized and screened in vitro for their cytotoxic activity against HL60, Nalm6, and Jurkat human leukemia cells as well as against B16F10 (melanoma cell line). In most cases, derivatives were able to reduce cell viability. The most potent compound (Z)-4-(((3,7-dimethylocta-2,6-dien-1-yl)oxy)methyl)-1-(4-(trifluoromethoxy)benzyl)1H-1,2,3 triazole showed antiproliferative activity against Jurkat cells and reduced B16F10 cell migration. Physicochemical properties of the compounds were calculated in order to evaluate their potential for drug development. Most of the evaluated physicochemical parameters seemed to be favorable for drug development. In addition, for a better understanding of the biological activity results, 3D quantitative structure-activity relationship (QSAR) studies were carried out. 3D-QSAR studies indicate that the anticancer activities observed for the cell lines HL60 and Jurkat may occur by a similar mechanism of action and the same was found for the Nalm6 and B16F10 cell lines.