(Z)-styryl 2-thienyl telluride | 144758-41-8

• 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: (Z)-styryl 2-thienyl telluride
• 英文别名: 2-[(Z)-2-phenylethenyl]tellanylthiophene
• CAS: 144758-41-8
• 化学式: C₁₂H₁₀STe
• 分子量: 313.877
• InChiKey: AOLARZHEXNMHQA-NTMALXAHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.75
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  28.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  异佛尔酮 、 (Z)-styryl 2-thienyl telluride 在 Li2[di-n-butylcyanocuprate] 、 三氟化硼乙醚 作用下， 以 四氢呋喃 为溶剂， 以70%的产率得到3,3,5-Trimethyl-5-((Z)-styryl)-cyclohexanone
  参考文献：
  名称：

  在受阻烯酮中添加Z-乙烯基高阶氰基甲酸酯。反应条件的影响

  摘要：

  由相应的Z-乙烯基碲化物制备的Z-乙烯基高级有色氰酸盐与二乙醚中或乙醚中的受阻烯酮有效反应。在纯THF中，受阻烯酮不能与以这种方式制备的Z-乙烯基氰脲酸酯反应。

  DOI：

  10.1016/s0040-4039(99)00951-x
• 作为产物：
  描述：

  双(噻吩-2-基)二碲化物 、 苯乙炔 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 24.0h， 以60%的产率得到(Z)-styryl 2-thienyl telluride
  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

• Higher order vinyl cyanocuprates from vinylic tellurides
  作者：Fábio C. Tucci、André Chieffi、João V. Comasseto

  DOI：10.1016/0040-4039(92)89015-5

  日期：1992.9

  Bis-vinylic tellurides, 1-tellurodienes, 1-telluroenynes and vinyl thienyl tellurides react with higher order cyanocuprates giving the corresponding higher order vinyl cyanocuprates with retention of the olefine geometry.
• Tellurium in Organic Synthesis. Preparation of <i>Z</i>-Vinylic Cuprates from <i>Z</i>-Vinylic Tellurides and Their Reaction with Enones and Epoxides
  作者：Fábio C. Tucci、André Chieffi、João V. Comasseto、Joseph P. Marino

  DOI：10.1021/jo951547c

  日期：1996.1.1

  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.
• Addition of Z-vinylic higher order cyanocuprates to hindered enones. The influence of the reaction conditions
  作者：M.A. Araújo、R.E. Barrientos-Astigarraga、R.M. Ellensohn、J.V. Comasseto

  DOI：10.1016/s0040-4039(99)00951-x

  日期：1999.7

  Z-Vinylic higher order cyanocuprates, prepared from the corresponding Z-vinylic tellurides, react efficiently with hindered enones in or in diethyl ether. In neat THF the hindered enones fail to react with Z-vinyl cyanocuprates prepared in this way.

  由相应的Z-乙烯基碲化物制备的Z-乙烯基高级有色氰酸盐与二乙醚中或乙醚中的受阻烯酮有效反应。在纯THF中，受阻烯酮不能与以这种方式制备的Z-乙烯基氰脲酸酯反应。