十二碳-3,4-二烯-2-酮 | 235746-26-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 十二碳-3,4-二烯-2-酮
• 英文名称: 3,4-dodecadien-2-one
• CAS: 235746-26-6
• 化学式: C₁₂H₂₀O
• 分子量: 180.29
• InChiKey: UQSVWRNPUPDJBL-UHFFFAOYSA-N

物化性质

• 沸点：
  269.5±7.0 °C(Predicted)
• 密度：
  0.834±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  13
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 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：

  甲基丙二酸二乙酯 、 十二碳-3,4-二烯-2-酮 在 potassium tert-butylate 作用下， 以 丙酮 为溶剂， 反应 0.17h， 以59%的产率得到(E)-4-(1,1-bis(ethoxycaronyl)ethyl)-4-dodecen-2-one
  参考文献：
  名称：

  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

  摘要：

  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.

  DOI：

  10.1016/j.tet.2005.01.131
• 作为产物：
  描述：

  N,N-二甲基乙酰胺 、 癸-1,2-二烯 在 盐酸 、 正丁基锂 作用下， 生成 十二碳-3,4-二烯-2-酮
  参考文献：
  名称：

  Hydrohalogenation Reaction of 1,2-Allenyl Ketones Revisited. Efficient and Highly Stereoselective Synthesis of β,γ-Unsaturated β-Haloketones

  摘要：

  DOI：

  10.1021/jo9903205

文献信息

• Palladium-Catalyzed Cyclization Reaction of Allylic Bromides with 1,2-Dienyl Ketones. An Efficient Synthesis of 3-Allylic Polysubstituted Furans
  作者：Shengming Ma、Lintao Li

  DOI：10.1021/ol0055871

  日期：2000.4.1

  3-Allylic polysubstituted furans were synthesized via a palladium-catalyzed cyclization reaction of allylic bromides with differently substituted 1,2-allenyl ketones. This process may occur via the reaction of a furanyl palladium intermediate with allylic bromide.

  3-烯丙基多取代的呋喃是通过钯催化的烯丙基溴与不同取代的1,2-烯基酮的环化反应合成的。该过程可以通过呋喃基钯中间体与烯丙基溴的反应而发生。
• 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 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.