3,4-壬二烯-2-酮 | 118893-64-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 3,4-壬二烯-2-酮
• 英文名称: 3,4-nonadien-2-one
• 英文别名: Nona-3,4-dien-2-one
• CAS: 118893-64-4
• 化学式: C₉H₁₄O
• 分子量: 138.21
• InChiKey: NLCNACWBDXXDHO-UHFFFAOYSA-N

物化性质

• 沸点：
  212.3±7.0 °C(Predicted)
• 密度：
  0.830±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  10
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.56
• 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：

  3,4-壬二烯-2-酮 在 IrH5(P-(i-Pr)3)2 作用下， 以 苯 为溶剂， 反应 24.0h， 以86%的产率得到壬-3,5-二烯-2-酮
  参考文献：
  名称：

  Highly stereoselective isomerization of ynones to conjugated dienones catalyzed by transition-metal complexes

  摘要：

  DOI：

  10.1021/jo00266a021
• 作为产物：
  描述：

  4-壬炔-2-酮 在 potassium carbonate 作用下， 以 水 为溶剂， 反应 4.0h， 以50%的产率得到3,4-壬二烯-2-酮
  参考文献：
  名称：

  Highly stereoselective isomerization of ynones to conjugated dienones catalyzed by transition-metal complexes

  摘要：

  DOI：

  10.1021/jo00266a021

文献信息

• Organocatalytic Asymmetric Conjugate Addition to Allenic Esters and Ketones
  作者：Petteri Elsner、Luca Bernardi、Giorgio Dela Salla、Jacob Overgaard、Karl Anker Jørgensen

  DOI：10.1021/ja710689c

  日期：2008.4.1

  having different ring sizes, ring systems, and substituents in high yields and enantioselectivities. Glycine imine derivatives also undergo the asymmetric conjugate addition to electron-deficient allenes in high yields and with enantioselectivities in the range of 60-88% ee, thus providing a rapid entry to optically active alpha-vinyl-substituted alpha-amino acid derivatives. It is shown that the enantioselectivity

  描述了环状β-酮酯和甘氨酸亚胺衍生物与缺电子丙二烯的有机催化对映选择性共轭加成的第一个例子。我们公开了相应的手性 β，γ-不饱和羰基化合物仅在相转移条件下使用金鸡纳生物碱衍生或联苯基手性季铵盐作为催化剂形成。β-酮酯的反应范围概述了具有酮或酯基序作为吸电子基团的丙二烯以及在 3 位具有不同取代基的丙二烯，从而以高产率和优异的非对映选择性和对映选择性得到旋光产物（ 90-96% ee)。对于许多具有不同环大小、环系统、和高产率和对映选择性的取代基。甘氨酸亚胺衍生物还以高产率与缺电子丙二烯进行不对称共轭加成，对映选择性在 60-88% ee 范围内，从而快速进入光学活性 α-乙烯基取代的 α-氨基酸衍生物。结果表明，对映选择性强烈依赖于亲核试剂的酯部分与所用催化体系的结合。这些新的催化过程产生的手性产物的高合成价值通过两种直接的转化得到证明，一种是光学活性的六氢苯并吡喃酮，另一种是取代的焦谷氨
• Pd0-Catalyzed Coupling Cyclization Reaction of Aryl or 1Alkenyl Halides with 1,2-Allenyl Ketones: Scope and Mechanism. An Efficient Assembly of 2,3,4-, 2,3,5-Tri- and 2,3,4,5-Tetrasubstituted Furans
  作者：Shengming Ma、Junliang Zhang、Lianghua Lu

  DOI：10.1002/chem.200204664

  日期：2003.6.6

  Described herein is the Pd(0)-catalyzed coupling cyclization reaction of 1,2-allenyl ketones with organic halides leading efficiently and conveniently to not only 2,3,4- and 2,3,5-trisubstituted furans but also 2,3,4,5-tetrasubstituted furans. Furthermore, this method showed high substituent-loading capability and tolerance of various substituents. The reactions of 1,2-allenyl ketones 1 e, 1 p, 1 q

  本文描述的是1,2-烯丙基酮与有机卤化物的Pd（0）催化的偶合环化反应，不仅有效且便捷地导致2,3,4-和2,3,5-三取代的呋喃，以及2,3 ，4,5-四取代的呋喃。此外，该方法显示出高的取代基负载能力和对各种取代基的耐受性。进行了1,2-烯基酮1e，1p，1q和氘代[D] 1c的反应，进行了机理研究，结果表明，该反应可能不是通过烯醇化途径，而是通过烯醇式中间体钯和分子内亲核试剂通过羰基氧攻击π-烯丙基钯中间体。
• Pd0-catalyzed cyclization reaction of aryl or alk-1-enyl halides with 1,2-dienyl ketones: a general and efficient synthesis of polysubstituted furans
  作者：Shengming Ma、Junliang Zhang

  DOI：10.1039/a908627g

  日期：——

  Under catalysis by Pd0 and Ag2CO3, the reaction of 1,2-allenyl ketones and organic halides in PhMe using Et3N as the base provides a new general access to polysubstituted furans with good to excellent yields.

  在 Pd0 和 Ag2CO3 的催化下，1,2-烯基酮和有机卤化物在 PhMe 中以 Et3N 为碱的反应提供了一种新的通用途径，可以得到具有良好至优异产率的多取代呋喃。
• Studies on t-BuOK-catalyzed Michael addition of 1,2-allenic ketones with 2-substituted diethyl malonates: highly selective synthesis of β,γ-unsaturated enones
  作者：Shengming Ma、Shichao Yu、Wenjian Qian

  DOI：10.1016/j.tet.2005.01.131

  日期：2005.4

  In this paper, we have demonstrated a facile nucleophilic addition of 2-substituted diethyl malonate to various substituted 1,2-allenic ketones to afford beta,gamma-unsaturated enones using a catalytic amount of t-BuOK as the base. The reaction usually completes within 10 min in acetone at room temperature. The stereoselectivity of the reaction with gamma-substituted allenic ketones is very high affording the beta,gamma-unsaturated E-enones. (c) 2005 Elsevier Ltd. All rights reserved.
• Studies on K₂CO₃-Catalyzed 1,4-Addition of 1,2-Allenic Ketones with Diethyl Malonate:  Controlled Selective Synthesis of β,γ-Unsaturated Enones and α-Pyrones
  作者：Shengming Ma、Shichao Yu、Shaohu Yin

  DOI：10.1021/jo034633i

  日期：2003.11.1

  The K2CO3 (10 mol %)-catalyzed 1,4-addition reaction of diethyl malonate with various substituted 1,2-allenic ketones leading to polyfunctionalized beta,gamma-unsaturated enones 3 or 4 was studied. With 3-unsubstituted 1-substituted-1,2-allenyl ketones, the highly selective formation of beta,gamma-unsaturated enones 4 was observed; with 1,2-allenyl ketones bearing one or two 3-substituents in the allenyl group, only beta,gamma-unsaturated enones 3 with an immigrated carbon-carbon double bond were produced; with 3-monosubstituted-1,2-allenyl ketones Z-beta,gamma-unsaturated enones 3 were formed with excellent stereoselectivity (E:Z > 96:4); with propadienyl ketones, mixtures of beta,gamma-unsaturated enones 3 and 4 were formed. alpha-Pyrone derivatives were synthesized via the K2CO3-catalyzed or -promoted reaction of 1,2-allenic ketones with diethyl malonate via a sequential Michael addition-carbon-carbon double bond migration-lactonization process.