dodeca-1,2-dien-4-one | 624740-61-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: dodeca-1,2-dien-4-one
• CAS: 624740-61-0
• 化学式: C₁₂H₂₀O
• 分子量: 180.29
• InChiKey: JLGUSRSXWPXGFR-UHFFFAOYSA-N

物化性质

• 沸点：
  269.8±7.0 °C(Predicted)
• 密度：
  0.828±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  13
• 可旋转键数：
  8
• 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 、 dodeca-1,2-dien-4-one 在 potassium tert-butylate 作用下， 以 丙酮 为溶剂， 反应 0.17h， 以66%的产率得到2-(1,1-bis(ethoxycarbonyl)ethyl)-1-dodecen-4-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：

  十二碳-1,2-二烯-4-醇 在 邻苯二甲酸二甲酯 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 dodeca-1,2-dien-4-one
  参考文献：
  名称：

  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

  摘要：

  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.

  DOI：

  10.1021/jo034633i

文献信息

• New Cationic Bisoxazoline-Au(III) Complex Catalyzed Cycloisomerization of 1-Allenyl-1-ethynyl Acetate
  作者：Keisuke Kato、Hiroyuki Akita、Takuya Kobayashi、Takeo Fujinami、Satoshi Motodate、Taichi Kusakabe、Tomoyuki Mochida

  DOI：10.1055/s-2008-1072655

  日期：——

  Treatment of 1-allenyl-1-diethynyl acetates in the presence of a Au or Pt catalyst (5 mol%) in toluene at room temperature, followed by methanolysis, gave 4-methylene-2-cyclopentenones. The new cationic bisoxazoline (box)-Au(III) complex (S,S)-Phbox- or [(R,R)-Bnbox AuCl2]SbF6} accelerated the reaction, providing the products in moderate yield (60-69%).

  室温下，在甲苯中使用金或铂催化剂（5 摩尔%）处理 1-烯基-1-二乙炔基乙酸酯，然后进行甲醇分解，可得到 4-亚甲基-2-环戊烯酮。新的阳离子双噁唑啉（box）-Au(III) 复合物 (S,S)-Phbox- 或 [(R,R)-Bnbox AuCl2]SbF6} 加快了反应速度，以中等产率（60-69%）提供了产物。
• Sc(OTf)₃-Catalyzed Indolylation of 1,2-Allenic Ketones:  Controlled Highly Selective Synthesis of β-Indolyl-α,β-unsaturetated (<i>E</i>)-Enones and β,β-Bisindolyl Ketones
  作者：Shengming Ma、Shichao Yu

  DOI：10.1021/ol052073z

  日期：2005.10.1

  A novel highly stereoselctive synthesis of beta-indolyl-alpha,beta-unsaturated (E)-enones by the hydroindolylation of the beta,gamma-C=C bond of 1,2-allenic ketones in the presence of 5 mol % Sc(OTf)(3) was developed. beta,beta-Bisindolyl ketones were prepared by using 2.5 equiv of indoles. A stepwise protocol for introducing different indoles was also established.
• 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.