(E)-1-chloro-non-1-en-3-yne | 77973-37-6

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 乙烯基卤化物
• 英文名称: (E)-1-chloro-non-1-en-3-yne
• 英文别名: (E)-1-chloronon-1-en-3-yne
• CAS: 77973-37-6
• 化学式: C₉H₁₃Cl
• 分子量: 156.655
• InChiKey: QOQROTINPWAKTM-CMDGGOBGSA-N

物化性质

• 沸点：
  192.4±23.0 °C(Predicted)
• 密度：
  0.947±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  10
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  (E)-1-chloro-non-1-en-3-yne 在 盐酸 、 正丁基锂 、 iron(III)-acetylacetonate 、 三氟化硼 、 二(3-甲基丁烷-2-基)硼烷 、 lithium 、 二溴三苯基膦 作用下， 以 四氢呋喃 、 N-甲基吡咯烷酮 、 六甲基磷酰三胺 、 乙醚 、 正己烷 、 二氯甲烷 为溶剂， 反应 15.92h， 生成 methyl (8Z,12E,14Z)-eicosa-8,12,14-trienoate
  参考文献：
  名称：

  Stereoselective synthesis of (6Z,10E,12Z)-octadeca-6,10,12-trienoic acid, (8Z,12E,14Z)-eicosa-8,12,14-trienoic acid, and their [1-14C]-radiolabeled analogs

  摘要：

  To study the metabolic fate of conjugated linoleic acid isomers, we synthesized, in seven steps, from 1-heptyne, (6Z,10E,12Z)-octadeca-6,10,12-trienoic acid, (8Z,12E,14Z)-eicosa-8,12,14-trienoic acid, and their [1-C-14]-analogs. In the case of (6Z,10E,12Z)-octadecatrienoic acid, a series of palladium-catalyzed cross-coupling reactions between 1-heptyne and (E)-1,2-dichloro-ethene, a coupling reaction with a Grignard reagent and cleavage of the dioxolane gave (E)-dodec-4-en-6-ynal 3. Stereoselective Wittig reaction between aldehyde 3 and triphenyl-[5-(tetrahydro-pyran-2-yloxy)-pentyl]-phosphonium provided a dienyne. Stereocontrolled reduction of the triple bond and replacement of the tetrahydropyranyl group by a bromine gave (5Z,9E,12Z)-1-bromoheptadeca-5.9,11-triene 10. Formation of the alkenyl lithium derivative and carbonation with CO2 furnished (6Z,10E,12Z)-octadecatrienoic acid. (8Z,12E,14Z)-eicosa-8,12,14-trienoic acid was obtained by the same route but using triphenyl-[5-(tetrahydropyran-2-yloxy)-heptyl]-phosphonium iodide for the Wittig reaction. [1-C-14]-analogs were obtained from the bromides by carbonation with (CO2)-C-14. In all cases, chemical or radiochemical purities were found to be better than 95% after purification by flash chromatography on silica gel (>99% after additional purification by RP-HPLC). Metabolism studies in animals are in progress. (C) 2003 Elsevier Science Ireland Ltd. All rights reserved.

  DOI：

  10.1016/s0009-3084(03)00049-5
• 作为产物：
  描述：

  反-1,2-二氯乙烯 以92%的产率得到
  参考文献：
  名称：

  Chemin Denis, Linstrumelle Gerard, Tetrahedron, 50 (1994) N 18, S 5335-5344

  摘要：

  DOI：

文献信息

• Sequential substitution of 1,2-dichloro-ethene: a convenient stereoselective route to (9Z,11E)-, (10E,12Z)- and (10Z,12Z)-[1-14C] conjugated linoleic acid isomers
  作者：O. Loreau、A. Maret、J.M. Chardigny、J.L. Sébédio、J.P. Noël

  DOI：10.1016/s0009-3084(00)00229-2

  日期：2001.3

  Conjugated linoleic acid (CLA) isomers are present in human foods derived from milk or ruminant meat. To study their metabolism, (9Z,11E)-, (10E,12Z)- and (10Z,12Z)-[1-(14)C]-octadecadienoic acids with high radiochemical and isomeric purities (>98%) were prepared by stereoselective multi-step syntheses involving sequential substitution of 1,2-dichloro-ethene. In the case of the (9Z,11E) isomer, a first

  共轭亚油酸（CLA）异构体存在于源自牛奶或反刍动物肉的人类食品中。为了研究它们的代谢，通过以下方法制备了具有高放射化学和异构纯度（> 98％）的（9Z，11E）-，（10E，12Z）-和（10Z，12Z）-[1-（14）C]-十八碳二烯酸。立体选择性多步合成，涉及顺序取代1,2-二氯乙烯。在（9Z，11E）异构体的情况下，由（7）-获得的（E）-1，2－二氯乙烯与2－非8－炔氧基－四氢吡喃之间的第一次金属催化的交叉偶联反应溴庚烷-1-醇，得到共轭的1，6-二炔。与己基溴化镁的第二次偶联反应提供了庚二炔基衍生物。立体选择性地还原三键和溴化得到（7E，9Z）-17-溴-庚烷-7，9-二烯。格氏试剂的形成并用14CO（2）碳酸化，得到（9Z，11E）-[1-（14）C]-十八烷基-9,11-二烯酸（7-溴-庚烷-1-醇的总产率为14.4％）。（10E，12Z）-和（10Z，12Z）-[1-（14）C]-十八烷基-10
• Synthesis of substituted quinolines by iron-catalyzed coupling reactions between chloroenynes and Grignard reagents
  作者：Matar Seck、Xavier Franck、Reynald Hocquemiller、Bruno Figadère、Jean-François Peyrat、Olivier Provot、Jean-Daniel Brion、Mouâd Alami

  DOI：10.1016/j.tetlet.2004.01.019

  日期：2004.2

  letter reports the preparation of quinolines, substituted at the 2- or 3-position by a 4-substituted but-3-en-1-yne group, by the environmentally friendly iron(III)-catalyzed coupling reaction of Grignard reagents with 1-chloro-4-(2-quinolyl)but-1-en-3-yne. The extension and the scope of this non-toxic and chemoselective procedure to various functionalized unsaturated vinyl chlorides are described.

  这封信报道了由环保的铁（III）催化的格氏试剂与1的环境友好的铁（III）偶联反应制备2-位或3-位被4-取代的丁-3-烯-1-炔基取代的喹啉。 -氯-4-（2-喹啉基）但是-1-烯-3-炔 描述了该无毒和化学选择性方法对各种官能化的不饱和氯乙烯的扩展和范围。
• Z-Stereoselective semi-reduction of alkynes: modification of the Boland protocol
  作者：Yasser M.A. Mohamed、Trond Vidar Hansen

  DOI：10.1016/j.tet.2013.03.038

  日期：2013.5

  Highly Z-selective semi-reduction of alkynes has been achieved by adding TMSCl to a mixture of Zn(Cu/Ag), water, and methanol. The conjugated Z-alkenes have been prepared in high yields at ambient temperature. The formation of isomeric E-alkenes and over-reduction to alkanes were suppressed in our modified Boland reduction protocol. The methodology was extended to the preparation of Z-substituted stilbenes

  通过将TMCSC1添加到Zn（Cu / Ag），水和甲醇的混合物中，可以实现炔烃的高度Z-选择性的半还原。在环境温度下已经以高收率制备了共轭Z-烯烃。在我们改进的Boland还原方案中，抑制了异构体E-烯烃的形成和烷烃的过度还原。该方法扩展到了Z-取代的对苯二甲酸酯的制备。
• Palladium-catalyzed reaction of (E) and (Z)-dichloroethenes with 1-alkynes. An efficient stereospecific synthesis of (E) and (Z)-enediynes.
  作者：Denis Chemin、Gerard Linstrumelle

  DOI：10.1016/s0040-4020(01)80691-8

  日期：1994.5

  The stereospecific sequential substitution of (E) and (Z)-dichloroethenes with 1-alkynes leads to (E) and (Z)-enediynes in high yield.

  （E）和（Z）-二氯乙烯被1-炔的立体有序顺序取代导致高产率的（E）和（Z）-二烯炔。
• Suzuki Coupling Reactions of (<i>E</i>)- and (<i>Z</i>)-Chloroenynes with Boronic Acids: Versatile Access to Functionalized 1,3-Enynes
  作者：Abdellatif Tikad、Abdallah Hamze、Olivier Provot、Jean-Daniel Brion、Mouâd Alami

  DOI：10.1002/ejoc.200901137

  日期：2010.2

  A stereoselective, palladium-catalyzed, cross-coupling reaction between chloroenynes 4 and boronic acids was successfully developed. This procedure is general and provides desired functionalized enynes 1 in high yields. The scope and limitations of this new reaction are described.

  成功开发了氯烯炔 4 和硼酸之间的立体选择性、钯催化的交叉偶联反应。该程序是通用的，并以高产率提供所需的官能化烯炔 1。描述了这种新反应的范围和限制。