(E)-2-Methyl-hept-2-en-6-ynoyl chloride | 313217-54-8

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 酰卤
• 英文名称: (E)-2-Methyl-hept-2-en-6-ynoyl chloride
• 英文别名: (E)-2-methylhept-2-en-6-ynoyl chloride
• CAS: 313217-54-8
• 化学式: C₈H₉ClO
• 分子量: 156.612
• InChiKey: JSJDTVDXCWRBEX-VOTSOKGWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  10
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (E)-2-Methyl-hept-2-en-6-ynoyl chloride 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 17.0h， 生成 (2E,8E,10R,11R,12E)-N-[2-[[3-(4-benzoylphenyl)-2,3-ditritiopropanoyl]amino]ethyl]-11-hydroxy-2,10,12-trimethyl-15-naphthalen-2-ylpentadeca-2,8,12-trien-6-ynamide
  参考文献：
  名称：

  Synthesis and preliminary analysis of a P-glycoprotein-specific [3H]-benzophenone photoaffinity label based on (−)-stipiamide

  摘要：

  A benzophenone photoaffinity label 9 based on the polyene natural product (-)-stipiamide has been constructed using a diaminoethane spacer and the radioactive agent [H-3]-BZDC (N-succinimidyl p-benzoyl-(2,3-H-3)-dehydrocinnamate). Photoaffinity experiments show specific binding to human P-glycoprotein (Pgp) in the presence of cis-flupentixol but not with cyclosporin A. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(00)00439-x
• 作为产物：
  描述：

  (2E)-2-methyl-2-hepten-6-ynoic acid 在 草酰氯 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 生成 (E)-2-Methyl-hept-2-en-6-ynoyl chloride
  参考文献：
  名称：

  Synthesis and preliminary analysis of a P-glycoprotein-specific [3H]-benzophenone photoaffinity label based on (−)-stipiamide

  摘要：

  A benzophenone photoaffinity label 9 based on the polyene natural product (-)-stipiamide has been constructed using a diaminoethane spacer and the radioactive agent [H-3]-BZDC (N-succinimidyl p-benzoyl-(2,3-H-3)-dehydrocinnamate). Photoaffinity experiments show specific binding to human P-glycoprotein (Pgp) in the presence of cis-flupentixol but not with cyclosporin A. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(00)00439-x

文献信息

• Synthesis and analysis of polyethylene glycol linked P-glycoprotein-specific homodimers based on (−)-stipiamide
  作者：Merritt B Andrus、Timothy M Turner、Emily P Updegraff、Zuben E Sauna、Suresh V Ambudkar

  DOI：10.1016/s0040-4039(01)00619-0

  日期：2001.6

  A series of five homodimeric polyethylene glycol (PEG) linked homodimers based on the multidrug resistance reversal agent (-)-stipiamide were made and tested fur their ability to interact with P-glycoprotein, the protein responsible for multidrug resistance, using ATPase and photoaffinity displacement assays. Key reactions include a new alkoxide-mesylate displacement for the assembly of the PEG linkers and a double Sunogashira coupling reaction. (C) 2001 Elsevier Science Ltd. All rights reserved.