(E)-5-(benzyloxy)-3-methylpent-2-en-1-ol | 151334-00-8

• 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: (E)-5-(benzyloxy)-3-methylpent-2-en-1-ol
• 英文别名: (2E)-5-benzyloxy-3-methylpent-2-en-1-ol；5-benzyloxy-(E)-3-methyl-2-penten-1-ol；(E)-3-methyl-5-phenylmethoxypent-2-en-1-ol
• CAS: 151334-00-8
• 化学式: C₁₃H₁₈O₂
• 分子量: 206.285
• InChiKey: KXYRYQZZAQQDJL-KPKJPENVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 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：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-5-(benzyloxy)-3-methylpent-2-en-1-ol 在 正丁基锂 、 三溴化磷 、 lithium 、 乙胺 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 17.83h， 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：

  ethyl (E)-5-(benzyloxy)-3-methylpent-2-enoate 在 二异丁基氢化铝 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 以79%的产率得到(E)-5-(benzyloxy)-3-methylpent-2-en-1-ol
  参考文献：
  名称：

  烯丙基酰肼的氧化 [2,3]-Sigmatropic 重排

  摘要：

  据报道，通过单线态 N-硝烯中间体开发了烯丙基酰肼的有效氧化 [2,3]-sigmatropic 重排。必需的烯丙基酰肼前体很容易制备，并在暴露于碘代苯后进行平滑的σ重排。这种新转化的产物被证明是各种化合物的有用前体。

  DOI：

  10.1021/ja2066219

文献信息

• Use of π-allyltricarbonyliron lactone complexes in the synthesis of taurospongin A: a potent inhibitor of DNA polymerase β and HIV reverse transcriptase
  作者：Christopher J. Hollowood、Shigeo Yamanoi、Steven V. Ley

  DOI：10.1039/b301676p

  日期：——

  The total synthesis of taurospongin A by two new approaches has been achieved where π-allyltricarbonyliron lactone complexes have been used to control highly stereoselective additions of the nucleophiles to a carbonyl unit located in the side chain of these complexes.

  已通过两种新方法成功合成了taurospongin A，其中使用了π-烯丙基三羰基铁内酯复合物来控制亲核试剂对这些复合物侧链中碳基单位的高立体选择性加成。
• The stereochemical course of tricho-acorenol biosynthesis
  作者：Christian A. Citron、Jeroen S. Dickschat

  DOI：10.1039/c3ob41755g

  日期：——

  The biosynthesis of tricho-acorenol in Trichoderma harzianum was investigated by feeding stereospecifically deuterated mevalonolactone isotopomers, followed by a detailed GC/MS analysis of the incorporation of labelling. The results establish a highly stereospecific hydride migration and antarafacial attack of water in the terminal step towards tricho-acorenol.

  通过喂食立体定向氘化的甲羟戊酸内酯异位异构体，然后进行标记的详细GC / MS分析，研究了哈茨木霉中木瓜醇的生物合成。结果建立了高度立体定向的氢化物迁移和水在反步骤中向三氯苯酚的反面侵蚀。
• An Oxidative [2,3]-Sigmatropic Rearrangement of Allylic Hydrazides
  作者：Benjamin F. Strick、Devon A. Mundal、Regan J. Thomson

  DOI：10.1021/ja2066219

  日期：2011.9.14

  The development of an efficient oxidative [2,3]-sigmatropic rearrangement of allylic hydrazides, via singlet N-nitrene intermediates, is reported. The requisite allylic hydrazide precursors are readily prepared and undergo smooth sigmatropic rearrangement upon exposure to iodosobenzene. The products of this novel transformation are shown to be useful precursors to a variety of compounds.

  据报道，通过单线态 N-硝烯中间体开发了烯丙基酰肼的有效氧化 [2,3]-sigmatropic 重排。必需的烯丙基酰肼前体很容易制备，并在暴露于碘代苯后进行平滑的σ重排。这种新转化的产物被证明是各种化合物的有用前体。
• 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.