Bishomogeranylbromid | 1000880-13-6

• 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: Bishomogeranylbromid
• 英文别名: bishomoneryl bromide
• CAS: 1000880-13-6
• 化学式: C₁₂H₂₁Br
• 分子量: 245.203
• InChiKey: CHIPFRKWSVNUAQ-WQLSENKSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.85
• 重原子数：
  13.0
• 可旋转键数：
  6.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  0.0

反应信息

• 作为反应物：
  描述：

  Bishomogeranylbromid 在 2,4,6-三甲基吡啶 、 sodium azide 、 三甲基溴硅烷 、 copper(II) sulfate 、 sodium ascorbate 作用下， 以 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 叔丁醇 为溶剂， 生成 sodium (4Z)-(2-(1-(5,9-dimethyldeca-4,8-dienyl)-1H-1,2,3-triazol-4-yl)ethane-1,1-diyl)bis(phosphonate)
  参考文献：
  名称：

  Bishomoisoprenoid triazole bisphosphonates as inhibitors of geranylgeranyl diphosphate synthase

  摘要：

  Protein geranylgeranylation reactions are dependent on the availability of geranylgeranyl diphosphate (GGDP), which serves as the isoprenoid donor. Inhibition of GGDP synthase (GGDPS) is of interest from a drug development perspective as GGDPS inhibition results in impaired protein geranylgeranylation, which in multiple myeloma, disrupts monoclonal protein trafficking and induces apoptosis. We have recently reported a series of isoprenoid triazole bisphosphonates and have demonstrated that a 3:1 mixture of homogeranyl and homoneryl isomers potently, and in a synergistic manner, inhibits GGDPS. We now present the synthesis and biological evaluation of a novel series of bishomoisoprenoid triazoles which furthers our understanding of the structure-function relationship of this class. These studies demonstrate the importance of chain length and olefin stereochemistry on inhibitory activity. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2017.02.066
• 作为产物：
  描述：

  (Z)-5,9-dimethyl-4,8-decadien-1-ol 在 三乙胺 、 lithium bromide 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 50.5h， 生成 Bishomogeranylbromid
  参考文献：
  名称：

  Bishomoisoprenoid triazole bisphosphonates as inhibitors of geranylgeranyl diphosphate synthase

  摘要：

  Protein geranylgeranylation reactions are dependent on the availability of geranylgeranyl diphosphate (GGDP), which serves as the isoprenoid donor. Inhibition of GGDP synthase (GGDPS) is of interest from a drug development perspective as GGDPS inhibition results in impaired protein geranylgeranylation, which in multiple myeloma, disrupts monoclonal protein trafficking and induces apoptosis. We have recently reported a series of isoprenoid triazole bisphosphonates and have demonstrated that a 3:1 mixture of homogeranyl and homoneryl isomers potently, and in a synergistic manner, inhibits GGDPS. We now present the synthesis and biological evaluation of a novel series of bishomoisoprenoid triazoles which furthers our understanding of the structure-function relationship of this class. These studies demonstrate the importance of chain length and olefin stereochemistry on inhibitory activity. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2017.02.066

文献信息

• Free-radical-mediated carbonylative cyclisation of alk-4-enyl halides leading to cyclopentanones
  作者：Ilhyong Ryu、Kazuya Kusano、Mitsuharu Hasegawa、Nobuaki Kannbe、Noboru Sonoda

  DOI：10.1039/c39910001018

  日期：——

  Alk-4-enyl bromides and iodides 1, when treated with the tributyltin hydride/CO system, undergo carbonylative cyclisation to give Cyclopentanones in good yields (AIBN cat., benzene, 75–90 atm, [1]= 0.025–0.05 mol dm–3, 80 °C, 2–3 h).

  当阿尔基-4-烯基溴化物和碘化物1与三丁基锡氢化物/一氧化碳体系反应时，发生羰基化环化反应，较高产率地生成环戊酮（AIBN催化，苯，75-90大气压，[1]= 0.025-0.05mol dm–3，80°C，2-3小时）。