5-benzyloxy-(E)-1-bromo-3-methyl-2-pentene | 244094-14-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5-benzyloxy-(E)-1-bromo-3-methyl-2-pentene
• 英文别名: [(E)-5-bromo-3-methylpent-3-enoxy]methylbenzene
• CAS: 244094-14-2
• 化学式: C₁₃H₁₇BrO
• 分子量: 269.181
• InChiKey: LLEXUEXXRLEKRF-KPKJPENVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 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：

  5-benzyloxy-(E)-1-bromo-3-methyl-2-pentene 在 正丁基锂 、 lithium 、 乙胺 作用下， 以 四氢呋喃 、 正己烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 17.5h， 生成 3,8,12,16-tetramethyl-3(E),7(E),11(E),15-heptadecatetraen-1-ol
  参考文献：
  名称：

  Amidrazone and Amidoxime Inhibitors of Squalene Hopene Cyclase

  摘要：

  The cyclization of squalene catalyzed by the enzyme squalene-hopene cyclase (SHC) leads to the hopanoid family of pentacyclic triterpenes, which are widely found in bacteria as membrane constituents. SHC mediates a cascade of regio- and stereoselective cyclizations that has triggered considerable interest in understanding the enzyme's mechanism of action. This paper reports synthetic studies leading to the preparation of trienylamidrazone 8, trienylamidoxime 9, and tetraenylamidoxime 10 corresponding to a partially cyclized squalene chain. All three compounds displayed significant levels of inhibition when assayed against SHC, with 9 being more active than 8, and amidoxime 10 being the most potent. Detailed profiles of their inhibition kinetics are also presented.

  DOI：

  10.1021/jo990237h
• 作为产物：
  描述：

  5-benzyloxy-2-pentyn-1-ol 在 copper(l) iodide 、 三溴化磷 、 红铝 作用下， 以 四氢呋喃 、 乙醚 、 甲苯 为溶剂， 反应 24.33h， 生成 5-benzyloxy-(E)-1-bromo-3-methyl-2-pentene
  参考文献：
  名称：

  Amidrazone and Amidoxime Inhibitors of Squalene Hopene Cyclase

  摘要：

  The cyclization of squalene catalyzed by the enzyme squalene-hopene cyclase (SHC) leads to the hopanoid family of pentacyclic triterpenes, which are widely found in bacteria as membrane constituents. SHC mediates a cascade of regio- and stereoselective cyclizations that has triggered considerable interest in understanding the enzyme's mechanism of action. This paper reports synthetic studies leading to the preparation of trienylamidrazone 8, trienylamidoxime 9, and tetraenylamidoxime 10 corresponding to a partially cyclized squalene chain. All three compounds displayed significant levels of inhibition when assayed against SHC, with 9 being more active than 8, and amidoxime 10 being the most potent. Detailed profiles of their inhibition kinetics are also presented.

  DOI：

  10.1021/jo990237h

文献信息

• Amidrazone and Amidoxime Inhibitors of Squalene Hopene Cyclase
  作者：Bruce Ganem、Yaohua Dong、Yi Feng Zheng、Glenn D. Prestwich

  DOI：10.1021/jo990237h

  日期：1999.7.1

  The cyclization of squalene catalyzed by the enzyme squalene-hopene cyclase (SHC) leads to the hopanoid family of pentacyclic triterpenes, which are widely found in bacteria as membrane constituents. SHC mediates a cascade of regio- and stereoselective cyclizations that has triggered considerable interest in understanding the enzyme's mechanism of action. This paper reports synthetic studies leading to the preparation of trienylamidrazone 8, trienylamidoxime 9, and tetraenylamidoxime 10 corresponding to a partially cyclized squalene chain. All three compounds displayed significant levels of inhibition when assayed against SHC, with 9 being more active than 8, and amidoxime 10 being the most potent. Detailed profiles of their inhibition kinetics are also presented.