(E)-7-hydroxyhept-3-en-2-one | 757231-85-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (E)-7-hydroxyhept-3-en-2-one
• CAS: 757231-85-9
• 化学式: C₇H₁₂O₂
• 分子量: 128.171
• InChiKey: JSVCFJVCVCQLMO-HWKANZROSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  9
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-7-hydroxyhept-3-en-2-one 在 (S)-(+)-alpha,alpha-二苯基脯氨醇 、 2-碘酰基苯甲酸 作用下， 以 二甲基亚砜 、 乙腈 为溶剂， 反应 5.0h， 以77%的产率得到(2E,4E)-6-oxohepta-2,4-dienal
  参考文献：
  名称：

  醇的立体选择性有机催化氧化为烯类：制备多烯的同源方法

  摘要：

  开发了一种新型的通过氧化烯胺催化的有机催化氧化方法，该方法与由简单的饱和醇直接合成烯类具有优异的相容性。通过使用这种胺催化的IBX氧化，广泛的...

  DOI：

  10.1039/c5cc10093c
• 作为产物：
  描述：

  (E)-7-((tert-butyldimethylsilyl)oxy)hept-3-en-2-one 在 溶剂黄146 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 2.0h， 以7%的产率得到(E)-7-hydroxyhept-3-en-2-one
  参考文献：
  名称：

  Thiourea/Proline Derivative-Catalyzed Synthesis of Tetrahydrofuran Derivatives: A Mechanistic View

  摘要：

  A thiourea/proline derivative-catalyzed synthesis of linear a-substituted tetrahydrofuran/pyran derivatives starting with lactol substrates is presented. This study demonstrates the utility and potential complications of using (thio)urea/proline cocatalysis as each of these catalysts is necessary to provide the observed reactivity, but a time-dependent decrease in enantioselectivity is observed. New mechanistic insights into (thio)urea/proline cocatalysis are presented.

  DOI：

  10.1021/jo200838v

文献信息

• Copper-catalyzed, stereoconvergent, cis-diastereoselective borylative cyclization of ω-mesylate-α,β-unsaturated esters and ketones
  作者：Ya-Jie Zuo、Xiao-Tong Chang、Zhi-Ming Hao、Chong-Min Zhong

  DOI：10.1039/c7ob01382e

  日期：——

  stereoconvergent borylative cyclization of ω-mesylate-α,β-unsaturated compounds is facilitated by a simple Cu-bisphosphine catalyst. This reaction provides a novel route to cis-β-boron-substituted five- and six-membered carbocycle and heterocycle esters. Mechanistic studies indicate that stereoconvergence and cis-substitution likely stem from the rapid enolation of the borylcopper adduct with the substrate

  简单的Cu-双膦催化剂可促进Cu（I）催化ω-甲磺酸酯-α，β-不饱和化合物的立体收敛性硼烷基化环化。该反应提供了一种顺式-β-硼取代的五元和六元碳环和杂环酯的新颖途径。机理研究表明，立体收敛和顺式取代可能分别源于硼铜铜加合物与底物双键的快速烯醇化和五元中间体的形成。
• Inter- and Intramolecular [4 + 1]-Cycloadditions Between Electron-Poor Dienes and Electron-Rich Carbenes
  作者：Claude Spino、Hadi Rezaei、Kristina Dupont-Gaudet、Francis Bélanger

  DOI：10.1021/ja046344x

  日期：2004.8.1

  Inter- and intramolecular [4 + 1]-annulations between dialkoxy carbenes and electron-deficient dienes afford mono- or bicyclic products in moderate to good yield.
• Activation of the reverse-Cope elimination by allylic oxygen functions: Syntheses of (−)-hygroline and (+)-pseudohygroline
  作者：David W. Knight、Rhys Salter

  DOI：10.1016/s0040-4039(99)01131-4

  日期：1999.8

  Reverse-Cope cyclisations of N-(4-alkenyl)hydroxylamines 8 are accelerated by the presence of the allylic oxygen function; this has been applied to a brief synthesis of the alkaloids (-)-hygroline 6 and (+)-pseudohygroline 7 (C) 1999 Elsevier Science Ltd. Ali rights reserved.
• Stereoselective organocatalytic oxidation of alcohols to enals: a homologation method to prepare polyenes
  作者：Xiaobei Chen、Yinan Zhang、Huixin Wan、Wei Wang、Shilei Zhang

  DOI：10.1039/c5cc10093c

  日期：——

  A novel organocatalytic oxidation through oxidative enamine catalysis was developed with excellent compatibility for the direct syntheses of enals from simple saturated alcohols. By using this amine-catalyzed IBX-oxidation, a wide...

  开发了一种新型的通过氧化烯胺催化的有机催化氧化方法，该方法与由简单的饱和醇直接合成烯类具有优异的相容性。通过使用这种胺催化的IBX氧化，广泛的...
• Thiourea/Proline Derivative-Catalyzed Synthesis of Tetrahydrofuran Derivatives: A Mechanistic View
  作者：Suzanne M. Opalka、Jeremy L. Steinbacher、Brandon A. Lambiris、D. Tyler McQuade

  DOI：10.1021/jo200838v

  日期：2011.8.19

  A thiourea/proline derivative-catalyzed synthesis of linear a-substituted tetrahydrofuran/pyran derivatives starting with lactol substrates is presented. This study demonstrates the utility and potential complications of using (thio)urea/proline cocatalysis as each of these catalysts is necessary to provide the observed reactivity, but a time-dependent decrease in enantioselectivity is observed. New mechanistic insights into (thio)urea/proline cocatalysis are presented.