Tellurophene, 3-(butyltelluro)-2,5-diphenyl- | 184843-54-7

• 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: Tellurophene, 3-(butyltelluro)-2,5-diphenyl-
• 英文别名: 3-butyltellanyl-2,5-diphenyltellurophene
• CAS: 184843-54-7
• 化学式: C₂₀H₂₀Te₂
• 分子量: 515.579
• InChiKey: WIFJYTIZNCPNPW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.63
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  3.0
• 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：

  4-甲氧基苯硼酸 、 Tellurophene, 3-(butyltelluro)-2,5-diphenyl- 在 四(三苯基膦)钯 、 三乙胺 、 silver(l) oxide 作用下， 以 甲醇 为溶剂， 以81%的产率得到3-(4-Methoxyphenyl)-2,5-diphenyltellurophene
  参考文献：
  名称：

  Copper Iodide-Catalyzed Cyclization of (Z)-Chalcogenoenynes

  摘要：

  We present here our results of the efficient copper-catalyzed cyclizations of chalcogenoenynes and establish a route to obtain 3-substituted chalcogenophenes in good to excellent yields. In addition, the obtained chalcogenophenes were readily transformed to more complex products using the palladium-catalyzed cross-coupling reactions with boronic acids to give Suzuki-type products in good yields.

  DOI：

  10.1021/ol802060f
• 作为产物：
  描述：

  (Z)-1,4-二苯基-1-丁烯-3-炔基-1-丁基碲化物 在 碲化氢 、 sodium tetrahydroborate 、 碘 作用下， 反应 0.83h， 生成 Tellurophene, 3-(butyltelluro)-2,5-diphenyl-
  参考文献：
  名称：

  Iodocyclization of (Z)-1-(Butyltelluro)-1,4-diorganylbut-1-en-3-ynes. Synthesis and Reactions of 3-Iodotellurophenes

  摘要：

  The iodocyclization of(Z)-tellurobutenynes 5a-g by reaction with I-2/petroleum ether was studied in detail. 3-Iodotellurophenes 7a-f were formed, and optimum conditions to obtain these compounds in high yields were established. The reaction involves attack of iodide at the initially formed intermediate of type 10 followed by ring closure that is favored by the strong aromatic character of the resulting products. Two possible and alternative pathways for the ring closure are proposed to explain our observations: (a) transformation of 10 to 11 that undergoes further cyclization to give 7a-f (pathway a) or (b) direct cyclization of 10 to give tellurophene diiodide 9 (pathway b). The products and side products obtained are in agreement with the proposed mechanisms. Formation of 7a from ditelluride 14 and iodine provides additional evidence of the intermediacy of 11 (in pathway a). Structures of 7a and 5g were elucidated by X-ray crystallography. In the case of compound 5e, where a terminal triple bond was present, the resulting intermediate of type 10 also underwent the attack of iodide directly at the terminal carbon to give compound 12 together with 7e. Ring-opening of 3-iodotellurophene 7a occurs by reaction with n-butyllithium to form acyclic ditelluride 14 or monotelluride 16 depending on. the alkyllithium amounts employed. Plausible mechanisms for these novel reactions are proposed and supported. Conversion of 7a to 3-(butyltelluro)-2,5-diphenyltellurophen (22) was carried out readily by an unusual ''aromatic nucleophilic substitution'' using the butyl tellurolate anion.

  DOI：

  10.1021/jo961461z

文献信息

• 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。
• Copper Iodide-Catalyzed Cyclization of (<i>Z</i>)-Chalcogenoenynes
  作者：André L. Stein、Diego Alves、Juliana T. da Rocha、Cristina W. Nogueira、Gilson Zeni

  DOI：10.1021/ol802060f

  日期：2008.11.6

  We present here our results of the efficient copper-catalyzed cyclizations of chalcogenoenynes and establish a route to obtain 3-substituted chalcogenophenes in good to excellent yields. In addition, the obtained chalcogenophenes were readily transformed to more complex products using the palladium-catalyzed cross-coupling reactions with boronic acids to give Suzuki-type products in good yields.
• Iodocyclization of (<i>Z</i>)-1-(Butyltelluro)-1,4-diorganylbut-1-en-3-ynes. Synthesis and Reactions of 3-Iodotellurophenes
  作者：Miguel J. Dabdoub、Vânia B. Dabdoub、Marco A. Pereira、Julio Zukerman-Schpector

  DOI：10.1021/jo961461z

  日期：1996.1.1

  The iodocyclization of(Z)-tellurobutenynes 5a-g by reaction with I-2/petroleum ether was studied in detail. 3-Iodotellurophenes 7a-f were formed, and optimum conditions to obtain these compounds in high yields were established. The reaction involves attack of iodide at the initially formed intermediate of type 10 followed by ring closure that is favored by the strong aromatic character of the resulting products. Two possible and alternative pathways for the ring closure are proposed to explain our observations: (a) transformation of 10 to 11 that undergoes further cyclization to give 7a-f (pathway a) or (b) direct cyclization of 10 to give tellurophene diiodide 9 (pathway b). The products and side products obtained are in agreement with the proposed mechanisms. Formation of 7a from ditelluride 14 and iodine provides additional evidence of the intermediacy of 11 (in pathway a). Structures of 7a and 5g were elucidated by X-ray crystallography. In the case of compound 5e, where a terminal triple bond was present, the resulting intermediate of type 10 also underwent the attack of iodide directly at the terminal carbon to give compound 12 together with 7e. Ring-opening of 3-iodotellurophene 7a occurs by reaction with n-butyllithium to form acyclic ditelluride 14 or monotelluride 16 depending on. the alkyllithium amounts employed. Plausible mechanisms for these novel reactions are proposed and supported. Conversion of 7a to 3-(butyltelluro)-2,5-diphenyltellurophen (22) was carried out readily by an unusual ''aromatic nucleophilic substitution'' using the butyl tellurolate anion.