(Z)-1,4-二苯基-1-丁烯-3-炔基-1-丁基碲化物 | 142025-08-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: (Z)-1,4-二苯基-1-丁烯-3-炔基-1-丁基碲化物
• 英文名称: (Z)-1,4-diphenyl-1-buten-3-ynyl 1-butyl telluride
• 英文别名: (Z)-1,4-diphenyl-1-(butyltelluro)-but-1-en-3-yne；(Z)-1-(butyltelluro)-1,4-diphenylbut-1-en-3-yne；(Z)-1-(butyltelluro)-1,4-diphenyl-1-buten-3-yne；[(Z)-1-butyltellanyl-4-phenylbut-1-en-3-ynyl]benzene
• CAS: 142025-08-9
• 化学式: C₂₀H₂₀Te
• 分子量: 387.979
• InChiKey: WCYLCZMLFDOGCU-SILNSSARSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.0
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 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：

  (Z)-1,4-二苯基-1-丁烯-3-炔基-1-丁基碲化物 在 正丁基锂 、 水 作用下， 生成 (E)-1,4-Diphenylbut-1-en-3-yne
  参考文献：
  名称：

  锂-碲交换反应在（Z）-1-丁基碲-1,4-双（有机基）but-1-上的锂-碲交换反应合成（E）-1,4-双（有机基）but-1-en-3-ynes en-3-ynes。

  摘要：

  1,4-双）有机基）-1,3-丁二炔与二丁基二碲化物和硼氢化钠在乙醇中在回流下反应生成（Z）-1-丁基碲-1,4-双（有机基）but-1-en-3 -ynes，先用丁基锂然后用水处理，以高收率得到（E）-1,4-双（有机基）but-1-en-3-ynes。

  DOI：

  10.1016/s0040-4039(00)74184-0
• 作为产物：
  描述：

  二丁基二碲 、 1，4-二苯基丁二炔 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以74%的产率得到(Z)-1,4-二苯基-1-丁烯-3-炔基-1-丁基碲化物
  参考文献：
  名称：

  Tellurium in Organic Synthesis. Preparation of Z-Vinylic Cuprates from Z-Vinylic Tellurides and Their Reaction with Enones and Epoxides

  摘要：

  Z-Vinylic tellurides, obtained with 100% stereoselectivity by the hydrotelluration of acetylenes, are easily transformed into Z-vinylic higher order cyanocuprates by reaction with preformed Me(2)Cu(CN)Li-2, n-Bu(2)Cu(CN)Li-2, or n-Bu(2-Th)Cu(CN)Li-2, with total retention of the double-bond configuration. The resulting vinylic higher order cyanocuprates react with unhindered enones to give the corresponding 1,4-addition products in good yields. Reaction of the vinylic higher order cyanocuprates with monosubstituted epoxides at 0 degrees C gives the homoallylic alcohols resulting from the attack to the less-substituted carbon atom, while the disubstituted epoxides failed to react. Allylic epoxides react at -78 degrees C with the vinylic higher order cyanocuprates to give mixtures of 1,2- and 1,4-opening products, the 1,4-product predominating. In all cases the double-bond configuration of the original vinylic telluride was preserved. The vinylic cuprates derived from simple vinylic tellurides and conjugated 1-telluroenynes react with epoxides at 0 degrees C, while vinylic cuprates derived from conjugated 1-tellurodienes required the addition of 1 equiv of BF3 . Et(2)O to give the homoallylic alcohols on reaction with epoxides. The opening of optically pure epoxides through tellurium/copper transmetalation is stereospecific, giving one single stereoisomer of the corresponding homoallylic alcohol.

  DOI：

  10.1021/jo951547c

文献信息

• Synthesis and antidepressant-like activity of selenophenes obtained viairon(iii)–PhSeSePh-mediated cyclization of Z-selenoenynes
  作者：Bibiana M. Gai、André L. Stein、Juliano A. Roehrs、Filipe N. Bilheri、Cristina W. Nogueira、Gilson Zeni

  DOI：10.1039/c1ob06548c

  日期：——

  We present here the synthesis and antidepressant-like action of a series of 2,5-disubstituted-3-(organoseleno)-selenophenes prepared by a novel synthetic route, the FeCl3–diorganyl dichalcogenide-mediated intramolecular cyclization of (Z)-chalcogenoenynes. The cyclized products were obtained in good yields. The results showed that 2c, 2d, 2e and 2o, evaluated in the mouse forced-swimming test, elicited an antidepressant-like activity. The studies clearly show that the phenyl group at the 2-position and an organoselenium group at the 3-position of the selenophene ring are essential for the antidepressant-like activity of selenophenes. A close inspection of the results also revealed that the fluorophenyl portion in the organoselenium group is fundamental for the antidepressant-like action of this class of organochalcogens.

  我们在此介绍了一系列 2,5-二取代-3-（有机硒）-硒苯的合成和抗抑郁样作用，这些硒苯是通过一种新的合成路线，即 FeCl3âdiorganyl dichalcogenide-mediated intramolecular cyclization of (Z)-chalcogenoenynes 制备的。环化产物的收率很高。结果表明，在小鼠强迫游泳试验中评估的 2c、2d、2e 和 2o 具有类似抗抑郁的活性。这些研究清楚地表明，硒吩环 2 位上的苯基和 3 位上的有机硒基团是硒吩类抗抑郁活性的关键。仔细观察研究结果还发现，有机硒基团中的氟苯基部分是这类有机致癌物抗抑郁作用的基础。
• Influence of the gegenion in the transmetalation reaction of vinylic tellurides with higher order cyanocuprates
  作者：André Chieffi、João V. Comasseto

  DOI：10.1016/s0040-4039(00)73112-1

  日期：1994.6

  Dilithium cyanocuprates R2LCu(CN)Li2 (L=2-Th, Me) react with vinylic tellurides of Z configuration, RCHCHTeR1 to give higher order vinylic cyanocuprates, [(RCHCH)LCu(CN)Li2]. By changing the gegenion from lithium to magnesium [R2LCu(CN)LiMgBr or R2LCu(CN)(MgBr)2] the reaction gives cross - coupling products of Z configuration, RCHCHR2 in good yields.

  二锂cyanocuprates - [R 2 LCU（CN）栗2（L = 2-Th时，Me）的具有乙烯型碲化物反应Ž配置，RCHCHTeR 1得到高阶乙烯基cyanocuprates，[（RCHCH）LCU（CN）栗2 ]。通过将锗酸根离子从锂变为镁[R 2 LCu（CN）LiMgBr或R 2 LCu（CN）（MgBr）2 ]，该反应以良好的收率得到了Z构型的交联产物RCH = CHR 2。
• 1-Phosphino-1,3-butadiene Derivatives Incorporated with Dibenzobarrelene Skeleton: Synthesis and Photophysical Properties
  作者：Akihiko Ishii、Chiharu Kikushima、Yuki Hayashi、Nobuhiko Ohtsuka、Norio Nakata、Atsuya Muranaka、Yusuke Tanaka、Masanobu Uchiyama

  DOI：10.1246/bcsj.20200190

  日期：2020.12.15

  An intramolecular [4+2] cycloaddition of 1-(9-anthrylchlorophosphino)-1,4-diphenylbut-1-en-3-yne produced the 1-(chlorophosphino)-1,4-diphenyl-1,3-butadiene derivative incorporated with a dibenzoba...

  1-(9-anthrylchlorophosphino)-1,4-diphenylbut-1-en-3-yne 的分子内 [4+2] 环加成反应生成 1-(chlorophosphino)-1,4-diphenyl-1,3-butadiene 衍生物与二苯并巴...
• Butyltellurium Tribromide: A Suitable Electrophilic Source to Cyclization Reactions
  作者：Gilson Zeni、Diego Alves、Marina Prigol、Cristina Nogueira

  DOI：10.1055/s-2008-1042926

  日期：2008.4

  We present here our results of the electrophilic cyclization reaction of (Z)-chalcogenoenynes using butyltellurium tribromide as an electrophilic source. The cyclization reaction proceeded cleanly under mild reaction conditions and 3-(butyltellanyl)chalcogenophenes were formed in moderate to excellent yields. Subsequent, using these heterocycles as substrate to palladium-catalyzed cross-coupling reactions a new carbon-carbon bond was formed in good yields.

  我们在此介绍使用三溴化丁基碲作为亲电源对 (Z)- 卤代烯炔进行亲电环化反应的结果。环化反应在温和的反应条件下顺利进行，生成的 3-(丁基碲基)链烯的产率为中等到极好。随后，以这些杂环为底物，在钯催化下进行交叉偶联反应，以良好的收率形成了新的碳-碳键。
• Synthesis and Photophysical Properties of Dibenzobarrelene-Incorporated 1,4-Diphenyl-1,3-pentadienes and a 5-Sila Derivative Having High Fluorescence Efficiency
  作者：Akihiko Ishii、Mari Shibata、Ryota Ebina、Norio Nakata

  DOI：10.1002/ejoc.201701616

  日期：2018.2.28

  dibenzobarrelene 1,3‐pentadienes and a sila derivative have been synthesized. They all show similar luminescence properties in CH2Cl2, whereas in the solid state, differences in the luminescence of the CH2 and SiMe2 derivatives and that of CHOH arise due to intermolecular hydrogen bonding in the latter. The fluorescence intensity of the SiMe2 derivative was markedly reduced by desilylation.

  合成了两种二苯并戊烯1,3-戊二烯和一种sila衍生物。它们在CH 2 Cl 2中都显示出相似的发光特性，而在固态下，由于后者中的分子间氢键，CH 2和SiMe 2衍生物的发光与CHOH的发光存在差异。SiMe 2衍生物的荧光强度通过去甲硅烷基化而显着降低。