(E)-3,8-壬二烯-2-酮 | 55282-90-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: (E)-3,8-壬二烯-2-酮
• 英文名称: nona-3t,8-dien-2-one
• 英文别名: 3,8-Nonadien-2-one；(3E)-nona-3,8-dien-2-one
• CAS: 55282-90-1
• 化学式: C₉H₁₄O
• 分子量: 138.21
• InChiKey: YKLUYYMKAUDXNV-BQYQJAHWSA-N

物化性质

• 沸点：
  215.3±19.0 °C(Predicted)
• 密度：
  0.848±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  10
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 海关编码：
  2914190090

反应信息

• 作为反应物：
  描述：

  (E)-3,8-壬二烯-2-酮 在 Stewart-Grubbs catalyst 、 双氧水 、 sodium hydroxide 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 C₁₆H₂₀O₃
  参考文献：
  名称：

  环氧和氮丙啶烯醇硅烷的化学选择性和非对映选择性分子内 (3+2) 环加成

  摘要：

  环氧和氮丙啶烯醇硅烷在非对映选择性分子内逐步 (3+2) 环加成反应中与无环二烯反应，几乎完全胜过 (4+3) 环加成途径。计算揭示了这种偏好背后的因素。可以产生光学富集的反式-氢化茚酮环加合物。

  DOI：

  10.1002/anie.202116099
• 作为产物：
  描述：

  5-己烯-1-醇 在 戴斯-马丁氧化剂 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 17.5h， 生成 (E)-3,8-壬二烯-2-酮
  参考文献：
  名称：

  稳定的偶氮甲碱叶立德和缺电子亲偶极试剂的[3+2]偶极环加成：区域选择性的修正

  摘要：

  稳定的偶氮甲碱叶立德与缺电子亲偶极试剂的 [3+2] 偶极环加成反应的区域选择性被发现与该杂志上发表的报告相反。

  DOI：

  10.1021/acs.joc.2c02629

文献信息

• Organomediated Morita−Baylis−Hillman Cyclization Reactions
  作者：Marie E. Krafft、Thomas F. N. Haxell

  DOI：10.1021/ja052146+

  日期：2005.7.1

  We have developed the Morita-Baylis-Hillman reaction to include, for the first time in a completely organomediated process, intramolecular examples bearing allylic leaving groups as the electrophilic partner providing a facile, high yielding, straightforward synthesis of densely functionalized cyclic molecules.

  我们开发了 Morita-Baylis-Hillman 反应，首次在完全有机介导的过程中包括带有烯丙基离去基团的分子内实例作为亲电伙伴，提供了一种简便、高产、直接合成密集功能化环状分子的方法。
• Visible light initiated photosensitised electron transfer (PET) reductive β-activation of α,β-unsaturated ketones for radical cyclisation: A new concept in promoting radical reactions
  作者：Ganesh Pandey、Saumen Hajra、Manas K. Ghorai

  DOI：10.1016/0040-4039(94)80131-2

  日期：1994.10

  Photosensitised one electron reductive β-activation of α,β-unsaturated ketones for radical cyclisations are reported.

  据报道，α，β-不饱和酮的光敏化一种电子还原性β-活化作用可用于自由基环化反应。
• Mass spectrometry in structural and stereochemical problems. CCXV. Behavior of phenyl-substituted .alpha.,.beta.-unsaturated ketones upon electron impact. Promotion of hydrogen rearrangement processes
  作者：R. J. Liedtke、A. F. Gerrard、J. Diekman、Carl Djerassi

  DOI：10.1021/jo00970a025

  日期：1972.3
• Reactions of enynes with adsorbed metal-carbenes
  作者：Thomas J. Katz、Ginger Xu-Qiang Yang

  DOI：10.1016/s0040-4039(00)79420-2

  日期：1991.10

  Adsorbed on silica-gel or on other adsorbants (MgSO4, Na2SO4, or Na2CO3), but not in homogeneous solution, pentacarbonyl(methoxyethylidene)chromium combines with simple enynes to give bicyclo[3.1.0]hexanes. The method's usefulness is illustrated by the synthesis of a variety of previously unknown structures from simple hydrocarbons, ethers, and amines.
• Designing Photosystems for Harvesting Photons into Electrons by Sequential Electron-Transfer Processes:  Reversing the Reactivity Profiles of α,β-Unsaturated Ketones as Carbon Radical Precursor by One Electron Reductive β-Activation
  作者：Ganesh Pandey、Saumen Hajra、Manas K. Ghorai、K. Ravi Kumar

  DOI：10.1021/ja9641564

  日期：1997.9.1

  Two photosystems are developed to harvest visible-light photons into electrons via sequential electron transfer processes. Photosystem-A (PS-A) consisted of DCA as light harvesting electron acceptor and Ph3P as sacrificial electron donor, whereas photosystem-B (PS-B) employed DCA as usual electron acceptor, DMN as a primary electron donor, and ascorbic acid as a secondary and sacrificial election donor. alpha,beta-Unsaturated ketones are utilized as secondary electron acceptors. The design of these photosystems is based on the thermodynamic feasibility of electron transfer between each participating components. Electron transfer from DCA(.-) to alpha,beta-unsaturated ketones leads to their beta-activation as carbon centered radicals which cyclizes efficiently to tethered activated olefins. Cyclization with a nonactivated olefin is found to be moderate. The cyclization stereochemistries have been illustrated by studying the PET activation of 5 and 21. The exclusive trans-stereochemistry observed in 8 is explained by considering the thermodynamic, equilibration of initially formed syn-intermediate 10 from 5. The isolation of trace amount of 9 in this reaction substantiates the syn-intermediacy as primary intermediate which is further confirmed by the isolation of 25 from 21. Formation of 25 suggests that wherever the syn-intermediate is thermodynamically more stable, it invariably undergoes further cyclization to geometrically well-placed enolate double bond. An interesting observation is made by isolating 9 as a major product from the PET activation of 5 using PS-B. Stabilization of 10 by ascorbic acid is suggested to be the plausible explanation for this unusual observation. Radicals produced by the reductive beta-activation of alpha,beta-unsaturated ketones follow well established radical cyclization rules which is exemplified by studying the reactions of 39 and 40. Generality of these cyclizations is demonstrated from the PET reactions of 29-32. Synthesis of 49, an important structural framework of biologically active angularly fused triquinanes, from 48 is included in this study to demonstrate the varied applicability of this strategy.