2-hexylethynyl methyl selenide

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: 2-hexylethynyl methyl selenide
• 英文别名: 1-Methylselanyloct-1-yne
• 化学式: C₉H₁₆Se
• 分子量: 203.186
• InChiKey: JAQSEXSNXIPPNL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.67
• 重原子数：
  10
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.78
• 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：

  2-hexylethynyl methyl selenide 在 lithium chloride 作用下， 以 溶剂黄146 为溶剂， 反应 6.0h， 以70%的产率得到(1Z)-1-Chloro-1-(methylselanyl)oct-1-ene
  参考文献：
  名称：

  A Novel Regio- and Stereoselective Hydrochlorination Reaction of Acetylenic Selenides; Highly Stereoselective Synthesis of (Z)-1-Chloro-1-seleno-1-enes and Stereodefined Selenoenynes

  摘要：

  (Z)-1-氯-1-硒-1-烯通过在醋酸中与炔烃硒化物反应，区域和立体选择性地合成。在5%毫摩尔的PdCl2(PhCN)2和10%毫摩尔的CuI存在下，(Z)-1-氯-1-硒-1-烯与末端炔烃快速耦合，得到了高产率的硒烯炔。

  DOI：

  10.1055/s-2000-8233

文献信息

• Copper-Catalyzed Cross-Coupling of Thiols with 1-Iodo-2-chalcogenoalkenes
  作者：Flávia Manarin、Juliano A. Roehrs、Ethel A. Wilhelm、Gilson Zeni

  DOI：10.1002/ejoc.200800495

  日期：2008.9

  We describe herein a new method for the synthesis of densely substituted alkenes containing chalcogenide atoms by a cross-coupling reaction between 1-iodo-2-chalcogenoalkenes and thiols using copper(I) as catalyst in a ligand-free system. The desired cross-coupling products were obtained in good yields and with satisfactory selectivity. The developed protocol tolerates a wide range of functional groups;

  我们在此描述了一种通过 1-iodo-2-硫属元素烯烃和硫醇之间的交叉偶联反应合成含有硫属元素原子的密集取代的烯烃的新方法，使用铜（I）作为无配体系统中的催化剂。以良好的产率和令人满意的选择性获得了所需的交叉偶联产物。开发的协议容忍广泛的功能组；在没有任何补充添加剂的情况下，探索了烷基、苄基和芳基硫醇与芳环上的中性、缺电子和富电子取代基的反应。此外，反应在温和的反应条件下顺利进行，并且对催化剂、碱和溶剂的性质很敏感。 (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)
• A One-pot Stereoselective Synthesis of 2-selenenyl-substituted 1,3-dienes by Hydrostannylation-Stille Tandem Reaction of Bu₃SnH with Acetylenic Selenides and Alkenyl Iodides
  作者：Wenyan Hao、Iamei Yu、Mingzhong Cai

  DOI：10.3184/030823407x200047

  日期：2007.3

  2-Selenenyl-substituted 1,3-dienes can be stereoselectively synthesised in one pot under mild conditions in good yields by the palladium-catalysed hydrostannylation of acetylenic selenides, followed by Stille coupling with alkenyl iodides.

  在温和的条件下，通过钯催化乙炔基硒化物的氢化锡，然后与烯基碘化物进行斯蒂尔偶联，可以在一锅内立体选择性地合成 2-硒基取代的 1,3 二烯，而且产量很高。
• Unique Regio- and Stereoselectivity in Pd-Catalyzed Chlorocarbonylation Reaction of 2-Phenylethynyl Selenides and 2-Alkylethynyl Selenides. Highly Stereoselective Synthesis of 2-Seleno-3-chloroacrylates
  作者：Xian Huang、Aiming Sun

  DOI：10.1021/jo0006977

  日期：2000.10.1

  Regio- and stereoselectivity in the chloropalladation carbonylation reaction of different acetylenic selenides in the presence of 0.05 equiv of PdCl2 and 3 equiv of cupric chloride under 1 atm of carbon monoxide affording 2-seleno-3-chloroacrylates were investigated. Opposite stereoselectivities were observed with 2-phenylethynyl selenides and 8-alkylethynyl selenides the reactions of 2-phenylethynyl selenides afforded (E)-2-seleno-3-chloro-3-phenylacrylates, while the reactions of 8-alkyl-ethynyl selenides gave (Z)-2-seleno-3-chloro-3-alkylacrylates. A chloropalladation carbonylation mechanism for this reaction was proposed. The regio- and stereoselective chloropalladation of the carbon-carbon triple bond in acetylenic selenides affords 1-enylpalladium intermediates, in which : the palladium atom connects with the carbon atom bonding with the selenium atom. Carbonylation in the presence of an alcohol affords 2-seleno-3-chloroacrylates.
• Zhong; Guo, Journal of Chemical Research - Part S, 2001, # 9, p. 370 - 371
  作者：Zhong、Guo

  DOI：——

  日期：——
• A stereoselective synthesis of 1,2-disubstituted alkenyl selenides via hydroboration-iodination of internal alkylselenoacetylenes with dicyclohexylborane
  作者：De Yu Yang、Xian Huang

  DOI：10.1016/0022-328x(96)06417-0

  日期：1996.10

  Selenoalkenyldicyclohexylboranes, prepared conveniently via hydroboration of internal alkylselenoacetylenes with dicyclohexylborane followed by iodination under basic conditions, produce cis/trans 1,2-disubstituted alkenyl selenides (1 and 2), which provide a general method for synthesis of cis/trans disubstituted alkenyl selenides containing a cyclohexyl group.