(hex-1-ynyl)(phenyl)selane | 68001-64-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (hex-1-ynyl)(phenyl)selane
• 英文别名: hex-1-yn-1-yl(phenyl)selane；Benzene, (1-hexynylseleno)-；hex-1-ynylselanylbenzene
• CAS: 68001-64-9
• 化学式: C₁₂H₁₄Se
• 分子量: 237.203
• InChiKey: NXERMBBWEMLZMW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.17
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 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：

  (hex-1-ynyl)(phenyl)selane 在 水 、 二异丁基氢化铝 作用下， 反应 28.0h， 生成 1-(phenylselenyl)-1-pentene
  参考文献：
  名称：

  Synthesis of ketene butyltelluro(phenylseleno)acetals by the Al/Te exchange reaction

  摘要：

  Hydroalumination of acetylenic selenides occurs, regiospecifically and the vinyl alanes obtained as intermediates were transformed into ketene butyltelluro (phenylseleno) acetals by the Al/Te exchange reaction using C4H9TeBr as electrophile. The stereoselectivity of the hydroalumination of chalcogeno acetylenes was confirmed by performing the hydrolysis of the vinyl alane intermediates that results in formation of the correponding Z phenylseleno alkenes with good yields.

  DOI：

  10.1016/0040-4039(95)02333-x
• 作为产物：
  描述：

  二苯基二硒醚 、 1-己炔 在 copper(l) iodide 作用下， 以 二甲基亚砜 为溶剂， 反应 48.0h， 以85%的产率得到(hex-1-ynyl)(phenyl)selane
  参考文献：
  名称：

  轻度条件下硒代炔烃的氧化羰基合成氧化还原中性酯

  摘要：

  据报道，从硒代炔烃开始，通过酸催化的，氧化还原-中性的氧化芳基化反应温和合成硒酸酯的方法。硒炔的布朗斯台德酸活化会生成硒稳定的乙烯基阳离子，该乙烯基阳离子会被芳基亚砜捕获并进行σ重排，从而生成最终的α-芳基硒酸酯产物。已经进行了计算研究以阐明硒稳定的碳正离子的性质。

  DOI：

  10.1021/acs.orglett.8b02544

文献信息

• Stereoselective synthesis of vinylic selenides
  作者：J.V. Comasseto、J.T.B. Ferreira、N. Petragnani

  DOI：10.1016/s0022-328x(00)85812-x

  日期：1981.8

  The addition of selenophenol to mono - and di-substituted unactivated acetylenes have been investigated. At room temperature the vinylic selenides obtained were predominantly of the Z configuration; at 120°C Z/E mixtures were produced. Vinylic selenides with the E configuration were obtained by reduction of the corresponding selenoacetylenes with lithium aluminium hydride.

  已经研究了将硒酚加到单和双取代的未活化乙炔中。在室温下，所获得的乙烯基硒化物主要为Z构型。在120℃下产生Z / E混合物。通过用氢化锂铝还原相应的硒乙炔，获得具有E构型的乙烯基硒化物。
• Regioselective Synthesis of Heteroatom-Functionalized Cyclobutene-triflones and Cyclobutenones
  作者：Benito Alcaide、Pedro Almendros、Carlos Lázaro-Milla

  DOI：10.1002/adsc.201700492

  日期：2017.8.7

  synthesis of a vast variety of heteroatom‐containing cyclobutene‐triflones [bis(trifluoromethylsulfonyl)cyclobutenes] and cyclobutenones has been developed starting from heteroatom‐substituted alkynes and a pyridinium salt (a latent Tf2C=CH2 source). This powerful methodology, involving cyclization reactions, allows for the selective preparation of oxygen‐, nitrogen‐, bromine‐, chlorine‐, iodine‐, sulfur‐

  从杂原子取代的炔烃和吡啶鎓盐（潜在的Tf 2 C = CH 2来源）开始，开发了可控制的无金属合成各种杂原子的环丁烯-triflones [双（三氟甲基磺酰基）环丁烯]和环丁烯酮。。这种强大的方法涉及环化反应，可以选择性地制备氧，氮，溴，氯，碘，硫，硒，碲，磷和硅官能化的环丁烯衍生物。
• A New Synthesis of <i>α</i>-Phenylseleno Esters and Acids from Terminal Alkynes
  作者：Marcello Tiecco、Lorenzo Testaferri、Andrea Temperini、Luana Bagnoli、Francesca Marini、Claudio Santi

  DOI：10.1055/s-2001-13370

  日期：——

  Alkynyl phenyl selenides, easily prepared from terminal alkynes, react with p-toluenesulfonic acid to afford (Z)-α-(phenylseleno)vinyl p-toluenesulfonates. The reactions of these compounds with phenylselenyl sulfate in the presence of alcohols or water give the corresponding α-phenylseleno esters or acids, respectively.

  炔基苯基硒化物可以从末端炔烃中易于合成，与对甲苯磺酸反应生成(Z)-α-(苯基硒代)乙烯对甲苯磺酸盐。这些化合物与苯基硒酸硫酯在醇或水存在下的反应，分别生成相应的α-苯基硒代酯或酸。
• Synthesis of SubstitutedSe-Phenyl Selenocarboxylates from Terminal Alkynes
  作者：Marcello Tiecco、Lorenzo Testaferri、Andrea Temperini、Luana Bagnoli、Francesca Marini、Claudio Santi、Raffaella Terlizzi

  DOI：10.1002/ejoc.200400177

  日期：2004.8

  Se-Phenyl selenocarboxylates have been conveniently prepared from (phenylseleno)acetylenes by treatment with p-toluenesulfonic acid monohydrate in dichloromethane. This easy conversion is compatible with a broad range of oxygen- and nitrogen-containing functional groups. The Se-phenyl selenocarboxylates were easily converted into the corresponding esters and amides. (© Wiley-VCH Verlag GmbH & Co. KGaA

  通过在二氯甲烷中用对甲苯磺酸一水合物处理，可以方便地从（苯基硒基）乙炔制备硒基羧酸硒苯酯。这种容易的转化与广泛的含氧和含氮官能团兼容。Se-苯基硒代羧酸盐很容易转化为相应的酯和酰胺。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)
• Mechanochemical Synthesis of Active Magnetite Nanoparticles Supported on Charcoal for Facile Synthesis of Alkynyl Selenides by C−H Activation
  作者：Balaji Mohan、Ji Chan Park、Kang Hyun Park

  DOI：10.1002/cctc.201600280

  日期：2016.7.20

  Magnetite (Fe3O4) nanoparticles supported on charcoal, graphene, or SBA‐15 were prepared by a simple solid‐state grinding technique and subsequent thermal treatment. The Fe3O4 nanoparticles supported on activated charcoal exhibited high catalytic activity and furnished good yields of the alkynyl selenide product in the cross‐coupling reaction of diphenyl diselenide and alkynes through activation of

  通过简单的固态研磨技术和随后的热处理制备了负载在木炭，石墨烯或SBA-15上的磁铁矿（Fe 3 O 4）纳米粒子。负载在活性炭上的Fe 3 O 4纳米颗粒表现出高催化活性，并在生态友好条件下通过活化C-H和Se-Se键，在二苯基二硒化物与炔烃的交叉偶联反应中提供了炔基硒化物产物的良好收率。传统的铜基催化剂可实现相同的有机转化。