undeca-1,2-dien-4-one

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: undeca-1,2-dien-4-one
• 化学式: C₁₁H₁₈O
• 分子量: 166.263
• InChiKey: PUXDFIBMNWXHID-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  12
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.64
• 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：

  undeca-1,2-dien-4-one 在 copper(II) bis(trifluoromethanesulfonate) 、 scandium tris(trifluoromethanesulfonate) 作用下， 以 乙腈 为溶剂， 反应 4.5h， 生成 2-(1H-3-indolyl)-2-(5-methyl-1H-3-indolyl)undecan-4-one
  参考文献：
  名称：

  Sc(OTf)₃-Catalyzed Indolylation of 1,2-Allenic Ketones:  Controlled Highly Selective Synthesis of β-Indolyl-α,β-unsaturetated (E)-Enones and β,β-Bisindolyl Ketones

  摘要：

  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.

  DOI：

  10.1021/ol052073z
• 作为产物：
  描述：

  1-十一碳炔-4-醇 在 Jones reagent 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 生成 undeca-1,2-dien-4-one
  参考文献：
  名称：

  回顾原位亲核试剂对艾伦酮的添加：苯并二恶英合成的一个入口。

  摘要：

  在存在碱的情况下，重新考虑向区域选择性地原位生成负亲核试剂至烯丙基酮。已开发出直接环环向苯并二恶英骨架合成的方法。在此过程中，获得的E-乙烯基酮很容易转化为砜和2,5-二取代的恶唑。

  DOI：

  10.1002/ejoc.202000076

文献信息

• Unprecedented Rearrangement of β-Difluoroboryloxy Ethers: A Route to C-2 Alkyl-chromenones
  作者：Debayan Sarkar、Sushree Ranjan Sahoo、Prathap Somu、Subhankar Paul、Peter Lönnecke

  DOI：10.1055/a-1833-8927

  日期：2022.10

  The addition of boron trifluoride etherate (BF3·OEt2) to allenic ketones has led to the isolation of the isolated boron difluoride enolates. The single-crystal structure of boron enolate has been solved. The unprecedented C1–C10 migration of (Z)-β-difluoroboryloxy ether derivatives is observed to deliver rearranged phenol derivatives which are functionalized to C-2 alkyl-chromenones. Interestingly

  将三氟化硼醚合物 (BF 3 ·OEt 2 ) 添加到烯酮中导致分离出的二氟化硼烯醇化物。已解决了烯醇硼的单晶结构。观察到 ( Z )-β-二氟硼氧基醚衍生物的前所未有的 C 1 -C 10迁移产生了重排的苯酚衍生物，这些衍生物被官能化为 C-2 烷基色酮。有趣的是，分离的硼烯醇化物表现出显着的抗癌特性。
• 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.
• Pd(CH₃CN)₂Cl₂-Catalyzed Oxidative Heterodimerization Reaction of 2,3-Allenamides and 1,2-Allenyl Ketones:  An Efficient Synthesis of 4-(Furan-3‘-yl)-2(5<i>H</i>)-furanimines
  作者：Shengming Ma、Zhenhua Gu、Zhanqian Yu

  DOI：10.1021/jo0507441

  日期：2005.8.1

  The Pd(II)-catalyzed oxidative heterodimerization reaction of 2,3-allenamides and 1,2-allenyl ketones was studied. It provides an efficient route for the synthesis of the polysubstituted 4-(furan-3'-yl)2(5H)-furanimines, which are not readily available from the known methods. Due to the application of benzoquinone, the loadings of both the palladium catalyst and ketone have been greatly reduced for the oxidative heterodimerization of 2,3-allenamides and 1,2-allenyl ketones in acetic acid.
• Revisiting the Addition of in-situ Nucleophiles to Allenic Ketones: An Entry Towards Synthesis of Benzodioxins
  作者：Sushree Ranjan Sahoo、Debayan Sarkar

  DOI：10.1002/ejoc.202000076

  日期：2020.3.22

  A revisit towards regioselective addition of in situ generated negative nucleophiles to allenic ketones in the presence of a base. A direct ring annulation towards the benzodioxin skeleton synthesis has been developed. In the process, the obtained E‐vinyl kenones were readily transformed into sulfones and 2,5‐disubstituted oxazole.

  在存在碱的情况下，重新考虑向区域选择性地原位生成负亲核试剂至烯丙基酮。已开发出直接环环向苯并二恶英骨架合成的方法。在此过程中，获得的E-乙烯基酮很容易转化为砜和2,5-二取代的恶唑。
• 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.