(Z)-1-(butyltelluro)-4-phenylbut-1-en-3-yne | 171667-57-5

• 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: (Z)-1-(butyltelluro)-4-phenylbut-1-en-3-yne
• 英文别名: (Z)-1-butyltelluro-4-phenyl-1-buten-3-yne；[(Z)-4-butyltellanylbut-3-en-1-ynyl]benzene
• CAS: 171667-57-5
• 化学式: C₁₄H₁₆Te
• 分子量: 311.881
• InChiKey: QDJMNHSVNWJVCZ-JYRVWZFOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.47
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• 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：

  (Z)-1-(butyltelluro)-4-phenylbut-1-en-3-yne 在 sodium tetrahydroborate 、 碘 作用下， 生成 3-Iodo-2-phenyl-tellurophene
  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
• 作为产物：
  描述：

  二丁基二碲 、 2-methyl-6-phenylhexa-3,5-diyn-2-ol 在 sodium hydroxide 、 sodium tetrahydroborate 作用下， 生成 (Z)-1-(butyltelluro)-4-phenylbut-1-en-3-yne
  参考文献：
  名称：

  非对称1,4-二有机基-1,3-丁二炔的高度化学选择性三键还原

  摘要：

  不对称的1.4-二有机基-1,3-丁二炔基la-g会进行rcturolatc阴离子的对位，立体和化学选择性加成，生成（Z）-1-丁基telluro-1,4-双（有机基）but-1-en-3 -ynes 2a-g的产量高。末端三键的反应快于炔丙基三键（醇衍生物），后者比带有烷基或芳基的三键反应性更高。从获得的产物中除去丁基碲部分的组合等同于1,3-丁二炔的一个三键的化学选择反式加氢-在THF中于-78°C用正丁基锂处理2c或2f提供了相应的（E）-不含碲的cnynes分别如图7a和7b所示。脱胶以绝对保留双键几何结构的方式发生。2b与正丁基锂反应原位生成的烯丙基锂8的硫酸二甲酯进行连续处理，生成不含碲9的（Z）-烯炔。8与CO 2的反应，然后酸化反应混合物，导致生成羧酸10还具有中心碳-碳双键的Z构型。

  DOI：

  10.1016/0040-4020(95)00564-o

文献信息

• Novel and general cross-coupling reactions of alkynylzinc reagents and organotellurium compounds
  作者：Miguel J. Dabdoub、Vânia B. Dabdoub、Joseph P. Marino

  DOI：10.1016/s0040-4039(99)02088-2

  日期：2000.1

  The efficient cross-coupling reactions of different alkynyl organozinc reagents with unsaturated organotellurium species catalyzed by Pd(PPh3)4/CuI and using THF/DMF systems are described. These cross-coupling reactions are general and permit the formation of new sp–sp 2 carbon–carbon bonds. New reactions to reach the necessary alkynylzinc intermediates were also developed from terminal alkynes or

  描述了不同的炔基有机锌试剂与Pd（PPh 3）4 / CuI并使用THF / DMF系统催化的不饱和有机碲物种的有效交叉偶联反应。这些交叉偶联反应很普遍，并允许形成新的sp–sp 2碳–碳键。还从末端炔烃或使用炔属碲化物作为起始原料开发了新的反应，以达到必要的炔基锌中间体。
• Novel cross-coupling reactions between organotellurides and Grignard reagents employing a MnCl2/CuI catalytic system
  作者：Marcio S. Silva、Renan S. Ferrarini、Bruno A. Sousa、Fabiano T. Toledo、João V. Comasseto、Rogério A. Gariani

  DOI：10.1016/j.tetlet.2012.04.134

  日期：2012.7

  We present a general protocol for the cross-coupling reaction of Grignard reagents and organic tellurides. Aryl Grignard reagents react stereospecifically with vinyl tellurides in the presence of a catalytic amount of manganese (II) chloride and copper (I) iodide to produce good yields of the corresponding cross-coupling products.

  我们提出了格氏试剂和有机碲化物交叉偶联反应的一般方案。在催化量的氯化锰（II）和碘化铜（I）的存在下，芳基格氏试剂与碲化乙烯立体定向反应，从而产生相应交叉偶联产物的良好收率。
• Highly chemoselective triple bond reductions on unsymmetrical 1,4-diorganyl-1,3-butadiynes
  作者：Miguel J Dabdoub、Vânia B. Dabdoub

  DOI：10.1016/0040-4020(95)00564-o

  日期：1995.1

  absolute retention of the double bond geometry In this way. sequential treatment with dimethyl sulfate of enynyl lithium 8 generated in situ by reaction of 2b with n-butyllithium produced the (Z)-enyne free of tellurium 9 The reaction of 8 with CO2 followed by acidification of the reaction mixture resulted in the formation of carboxylic acid 10 also with the central carbon-carbon double bond of Z configuration

  不对称的1.4-二有机基-1,3-丁二炔基la-g会进行rcturolatc阴离子的对位，立体和化学选择性加成，生成（Z）-1-丁基telluro-1,4-双（有机基）but-1-en-3 -ynes 2a-g的产量高。末端三键的反应快于炔丙基三键（醇衍生物），后者比带有烷基或芳基的三键反应性更高。从获得的产物中除去丁基碲部分的组合等同于1,3-丁二炔的一个三键的化学选择反式加氢-在THF中于-78°C用正丁基锂处理2c或2f提供了相应的（E）-不含碲的cnynes分别如图7a和7b所示。脱胶以绝对保留双键几何结构的方式发生。2b与正丁基锂反应原位生成的烯丙基锂8的硫酸二甲酯进行连续处理，生成不含碲9的（Z）-烯炔。8与CO 2的反应，然后酸化反应混合物，导致生成羧酸10还具有中心碳-碳双键的Z构型。
• 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.