(Cyclohex-1-enylethynylselanyl)-benzene | 104953-94-8

• 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: (Cyclohex-1-enylethynylselanyl)-benzene
• 英文别名: 2-(Cyclohexen-1-yl)ethynylselanylbenzene
• CAS: 104953-94-8
• 化学式: C₁₄H₁₄Se
• 分子量: 261.225
• InChiKey: IZWIJZYRLIMOSS-UHFFFAOYSA-N

物化性质

• 沸点：
  142 °C(Press: 0.02 Torr)

计算性质

• 辛醇/水分配系数(LogP)：
  2.48
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 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：

  (Cyclohex-1-enylethynylselanyl)-benzene 在 水 、 二异丁基氢化铝 作用下， 生成 (Z)-1-(phenylseleno)-2-(1-cyclohexen-1-yl)ethene
  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：

  1-乙炔基环己烷 、 苯基溴化硒 在 copper(l) iodide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以52%的产率得到(Cyclohex-1-enylethynylselanyl)-benzene
  参考文献：
  名称：

  在碘化铜（I）存在下，由末端炔烃和异戊烯基硫属卤化物方便地制备炔基硒化物，硫化物和碲化物

  摘要：

  炔基硒化物，硫化物和碲化物是在非常温和的条件下，通过使末端炔烃与苯基硫属酰基卤化物在碘化铜（I）存在下反应而获得的。

  DOI：

  10.1016/s0040-4039(00)61445-4

文献信息

• Redox-Neutral Synthesis of Selenoesters by Oxyarylation of Selenoalkynes under Mild Conditions
  作者：Lucas L. Baldassari、Anderson C. Mantovani、Samuel Senoner、Boris Maryasin、Nuno Maulide、Diogo S. Lüdtke

  DOI：10.1021/acs.orglett.8b02544

  日期：2018.9.21

  selenoalkynes through an acid-catalyzed, redox-neutral oxyarylation reaction is reported. Brønsted acid activation of a selenoalkyne leads to a selenium-stabilized vinyl cation, which is captured by an aryl sulfoxide and undergoes sigmatropic rearrangement to deliver the final α-arylated selenoester product. Computational studies have been carried out to elucidate the nature of the Se-stabilized carbocation

  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。
• 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。
• Hydroalumination of selenoacetylenes: a versatile generation and reactions of α-aluminate vinyl selenide intermediates in the highly regio and stereoselective synthesis of telluro(seleno)ketene acetals
  作者：Palimécio G. Guerrero、Miguel J. Dabdoub、Adriano C.M. Baroni

  DOI：10.1016/j.tetlet.2008.04.072

  日期：2008.6

  (Z)-butylseleno vinyl alanates intermediates which were captured with C4H9TeBr furnishing the (E)-telluro(seleno)ketene acetals exclusively. The isomers with opposite stereochemistry (Z)-telluro(seleno)ketene acetals were obtained by the reduction of phenylseleno acetylenes with lithium di-(isobutyl)-n-butyl aluminate hydride (Zweifel’s reagent) followed by reaction of (E)-phenylseleno vinyl alanates intermediates

  丁基硒炔乙炔与DIBAL-H的氢铝化反应，然后添加原位生成的（Z）-丁基硒代乙烯基丙二酸酯中间体，用C 4 H 9 TeBr捕获的正丁基锂，专门提供（E）-碲基（硒代）乙烯酮缩醛。通过用二（异丁基）-正丁基铝酸氢化铝锂（Zweifel试剂）还原苯基硒基乙炔，然后使（E）-苯基硒基乙烯基化合物反应，可获得具有相反立体化学（Z）-碲（硒基）乙烯酮缩醛的异构体用C 4 H 9 TeBr丙酸酯中间体。
• Formation of dimeric acetylenes: an unexpected reaction of acetylenic selenides
  作者：Jo�o V. Comasseto、Valdomiro Catani、Jos� T. B. Ferreira、Antonio L. Braga

  DOI：10.1039/c39860001067

  日期：——

  1-Selenoalk-1-ynes react with m-chloroperoxybenzoic acid in tetrahydrofuran–water furnishing 1,4-disubstituted 1,3-diynes free of selenium in high yield.

  1-Selenoalk -1-炔与反应米氯过氧苯甲酸在四氢呋喃-水家具1,4-二取代-1,3-二炔以高收率自由硒。
• Comasseto, Joao V.; Silveira, Claudio C.; Ferreira, Jose T. B., Synthetic Communications, 1986, vol. 16, # 3, p. 283 - 290
  作者：Comasseto, Joao V.、Silveira, Claudio C.、Ferreira, Jose T. B.、Catani, Valdomiro

  DOI：——

  日期：——