(2E,4E,6E)-ethyl undeca-2,4,6-trienoate | 76896-89-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (2E,4E,6E)-ethyl undeca-2,4,6-trienoate
• 英文别名: ethyl (2E,4E,6E)-undeca-2,4,6-trienoate
• CAS: 76896-89-4
• 化学式: C₁₃H₂₀O₂
• 分子量: 208.301
• InChiKey: WKNXYBPJRCFJPG-SNUJAXHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  15
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2E,4E,6E)-ethyl undeca-2,4,6-trienoate 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 生成 (2E,4E,6E)-Undeca-2,4,6-trien-1-ol
  参考文献：
  名称：

  Novel synthesis of phenol derivatives by palladium-catalyzed cyclocarbonylation of 2,4-pentadienyl acetates

  摘要：

  Phenyl acetates were selectively obtained in good yields by cyclocarbonylation of 2,4-pentadienyl acetates in the presence of NEt3, Ac2O, and a catalytic amount of palladium complexes such as PdCl2(PPh3)2 at 120-140-degrees-C under 50 atm of CO. No five-membered ring products were observed. A platinum complex PtCl2(PPh3)2 was also effective as a catalyst. The reaction of 5-phenyl-2,4-pentadienyl bromide with M(CO)(PPh3)3 (M = Pd or Pt) under CO gave the corresponding 6-phenyl-3, 5-hexadienoyl complexes in a high yield, which in turn afforded 2-acetoxybiphenyl in 41-51% yield on heating to 160-degrees-C under 50 atm of CO in the presence of NEt3 and Ac2O. Similar 3,5-hexadienoyl complexes are proposed to be intermediates in the catalytic cyclocarbonylation of 2,4-pentadienyl acetates. On the other hand, PdCl2(PPh3)2-catalyzed carbonylation of o-(bromomethyl)(1-alkenyl)-benzenes in the presence of NEt3 and Ac2O gave 2-naphthyl acetates in moderate yields, while the reaction in the absence of Ac2O gave five-membered ring products such as 2-indanones or a tricyclic lactone by incorporation of one or two CO molecules, respectively.

  DOI：

  10.1021/jo00076a051
• 作为产物：
  描述：

  反式-2-已烯-1-醇 在 lithium aluminium tetrahydride 、 乙基溴化镁 、 copper(l) cyanide 、 草酸 、 三溴化磷 、 sodium hydride 、 2-碘酰基苯甲酸 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 36.5h， 生成 (2E,4E,6E)-ethyl undeca-2,4,6-trienoate
  参考文献：
  名称：

  Novel triacsin C analogs as potential antivirals against rotavirus infections

  摘要：

  Recently our group has demonstrated that cellular triglyceride (TG) levels play an important role in rotavirus replication. In this study, we further examined the roles of the key enzymes for TG synthesis (lipogenesis) in the replication of rotaviruses by using inhibitors of fatty acid synthase, long chain fatty acid acyl-CoA synthetase (ACSL), and diacylglycerol acyltransferase and acyl-CoA:cholesterol acyltransferase in association with lipid droplets of which TG is a major component. Triacsin C, a natural ACSL inhibitor from Streptomyces aureofaciens, was found to be highly effective against rotavirus replication. Thus, novel triacsin C analogs were synthesized and evaluated for their efficacies against the replication of rotaviruses in cells. Many of the analogs significantly reduced rotavirus replication, and one analog (1e) was highly effective at a nanomolar concentration range (ED50 0.1 mu M) with a high therapeutic index in cell culture. Our results suggest a crucial role of lipid metabolism in rotavirus replication, and triacsin C and/or its analogs as potential therapeutic options for rotavirus infections. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.02.010

文献信息

• Isomerization of Electron-Poor Alkynes to the Corresponding (E,E)-1,3-Dienes Using a Bifunctional Polymeric Catalyst Bearing Triphenylphosphine and Phenol Groups
  作者：Patrick Toy、Cathy Kwong、Michael Fu、Henry Law

  DOI：10.1055/s-0030-1258576

  日期：2010.10

  The use of a bifunctional non-cross-linked polystyrene bearing both phosphme and phenol groups tor the organocatalytic isomerization of alkynes bearing electron-withdrawing ester substituents to afford the corresponding (E,E)-dienes in excellent yield and stereoselectivity is described. When polystyrene functionalized with only phosphine groups was used as the catalyst, either low or no yield of the

  描述了使用带有膦基和苯酚基团的双官能非交联聚苯乙烯对带有吸电子酯取代基的炔烃进行有机催化异构化，以优异的产率和立体选择性提供相应的 (E,E)-二烯。当仅用膦基团官能化的聚苯乙烯用作催化剂时，所需产物的收率低或没有收率。因此，双功能聚苯乙烯催化剂的两个官能团对于有效催化的发生都是必不可少的。这种双功能聚合物催化剂还用于从相应的炔烃合成 (E,E,E)-三烯和 (E,E)-二烯取代的 2(H)-吡喃-2-酮。
• On the Mechanism of Cu-Catalyzed Enantioselective Extended Conjugate Additions: A Structure-Based Approach
  作者：Tim den Hartog、Yange Huang、Martín Fañanás-Mastral、Anne Meuwese、Alena Rudolph、Manuel Pérez、Adriaan J. Minnaard、Ben L. Feringa

  DOI：10.1021/cs501297s

  日期：2015.2.6

  The enantioselective 1,6-addition to unsaturated carbonyl compounds offers unique opportunities to study the range of selectivities one can obtain using Cu catalysis. Here, a substrate–reagent approach to obtain structural information on the mechanism of extended conjugate additions is reported. By studying the influence of several halides in the Grignard reagent and in the Cu source on the enantioselective

  对不饱和羰基化合物的1,6-对映选择性加成提供了独特的机会来研究使用Cu催化可获得的选择性范围。在这里，报道了一种底物-试剂方法来获得有关扩展缀合物加成机理的结构信息。通过研究格氏试剂和铜源中几种卤化物对对映选择性1,6-加成的影响，表明使用EtMgBr作为格氏试剂和CuI作为铜源的组合是有利的。此外，探索带有几种烷基酯的底物发现，叔丁基酯底物增强了1,6-加成中的对映异构，并允许添加BnCH 2溴化镁。还研究了具有各种吸电子基团的底物，确定酯底物最适合1,6加成。其他两项研究的重点是Me取代的烯烃底物和具有所有可能的烯烃几何形状的底物。这些研究表明，当使用α-Me底物时，在1,6-加成中空前的高对映选择性，并为1,6-加成机理提供了相关见解。最后，研究了具有三个或四个烯烃与吸电子基团共轭的底物。在此，报道了1，8-加成，其以合理的产率，区域选择性和立体选择性给出了相应的产物。结合这些研究
• Soft Propargylic Deprotonation: Designed Ligand Enables Au-Catalyzed Isomerization of Alkynes to 1,3-Dienes
  作者：Zhixun Wang、Yanzhao Wang、Liming Zhang

  DOI：10.1021/ja503909c

  日期：2014.6.25

  By functionalizing the privileged biphenyl-2-ylphosphine with a basic amino group at the rarely explored 3' position, the derived gold(I) complex possesses orthogonally positioned "push" and "pull" forces, which enable for the first time soft propargylic deprotonation and permit the bridging of a difference of >26 pK(a) units (in DMSO) between a propargylic hydrogen and a protonated tertiary aniline. The application of this design led to efficient isomerization of alkynes into versatile 1,3-dienes with synthetically useful scope under mild reaction conditions.
• Novel synthesis of phenol derivatives by palladium-catalyzed cyclocarbonylation of 2,4-pentadienyl acetates
  作者：Youichi Ishii、Chao Gao、Wen Xiang Xu、Masakazu Iwasaki、Masanobu Hidai

  DOI：10.1021/jo00076a051

  日期：1993.11

  Phenyl acetates were selectively obtained in good yields by cyclocarbonylation of 2,4-pentadienyl acetates in the presence of NEt3, Ac2O, and a catalytic amount of palladium complexes such as PdCl2(PPh3)2 at 120-140-degrees-C under 50 atm of CO. No five-membered ring products were observed. A platinum complex PtCl2(PPh3)2 was also effective as a catalyst. The reaction of 5-phenyl-2,4-pentadienyl bromide with M(CO)(PPh3)3 (M = Pd or Pt) under CO gave the corresponding 6-phenyl-3, 5-hexadienoyl complexes in a high yield, which in turn afforded 2-acetoxybiphenyl in 41-51% yield on heating to 160-degrees-C under 50 atm of CO in the presence of NEt3 and Ac2O. Similar 3,5-hexadienoyl complexes are proposed to be intermediates in the catalytic cyclocarbonylation of 2,4-pentadienyl acetates. On the other hand, PdCl2(PPh3)2-catalyzed carbonylation of o-(bromomethyl)(1-alkenyl)-benzenes in the presence of NEt3 and Ac2O gave 2-naphthyl acetates in moderate yields, while the reaction in the absence of Ac2O gave five-membered ring products such as 2-indanones or a tricyclic lactone by incorporation of one or two CO molecules, respectively.
• Novel triacsin C analogs as potential antivirals against rotavirus infections
  作者：Yunjeong Kim、David George、Allan M. Prior、Keshar Prasain、Shuanghong Hao、Duy D. Le、Duy H. Hua、Kyeong-Ok Chang

  DOI：10.1016/j.ejmech.2012.02.010

  日期：2012.4

  Recently our group has demonstrated that cellular triglyceride (TG) levels play an important role in rotavirus replication. In this study, we further examined the roles of the key enzymes for TG synthesis (lipogenesis) in the replication of rotaviruses by using inhibitors of fatty acid synthase, long chain fatty acid acyl-CoA synthetase (ACSL), and diacylglycerol acyltransferase and acyl-CoA:cholesterol acyltransferase in association with lipid droplets of which TG is a major component. Triacsin C, a natural ACSL inhibitor from Streptomyces aureofaciens, was found to be highly effective against rotavirus replication. Thus, novel triacsin C analogs were synthesized and evaluated for their efficacies against the replication of rotaviruses in cells. Many of the analogs significantly reduced rotavirus replication, and one analog (1e) was highly effective at a nanomolar concentration range (ED50 0.1 mu M) with a high therapeutic index in cell culture. Our results suggest a crucial role of lipid metabolism in rotavirus replication, and triacsin C and/or its analogs as potential therapeutic options for rotavirus infections. (C) 2012 Elsevier Masson SAS. All rights reserved.