(Z)-(2-cyclohexenyl-1-ethenyl)butyltelluride | 173439-74-2

• 分子结构分类: 有机化合物 - 有机氧化合物 - 有机含氧阴离子化合物
• 英文名称: (Z)-(2-cyclohexenyl-1-ethenyl)butyltelluride
• 英文别名: Z-(2-cyclohexenyl-1-ethenyl)butyltelluride；1-[(Z)-2-butyltellanylethenyl]cyclohexene
• CAS: 173439-74-2
• 化学式: C₁₂H₂₀Te
• 分子量: 291.891
• InChiKey: LJZURXNZIZMIPG-LUAWRHEFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.92
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 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：

  异丙醇频哪醇硼酸酯 、 (Z)-(2-cyclohexenyl-1-ethenyl)butyltelluride 在 正丁基锂 作用下， 以 hexanes 、 乙醚 为溶剂， 以75%的产率得到(Z)-2-(2-(cyclohex-1-en-1-yl)vinyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
  参考文献：
  名称：

  Synthesis of cis-vinyltrimethylstannanes and cis-vinylpinacolboronates in a two-step highly regio and stereoselective process

  摘要：

  A highly efficient two-step regio and stereoselective method for the synthesis of both cis-vinyltrimethylstannanes and cis-vinylpinacolboronates is described. This method takes advantage of the known lithium/tellurium exchange pathway providing a versatile alternative to known literature methods The methodology presented demonstrates compatibility, for example, with substrates bearing oxygen functionality in comparison to previously reported methods of cis-selective hydrostannylation (i.e., ZrCl4) (C) 2009 Elsevier Ltd. All rights reserved

  DOI：

  10.1016/j.tet.2009.06.092
• 作为产物：
  描述：

  1-(2-Butyltellanylethynyl)cyclohexene 在 二异丁基氢化铝 作用下， 以 正己烷 、 甲苯 为溶剂， 反应 2.0h， 以47%的产率得到(Z)-(2-cyclohexenyl-1-ethenyl)butyltelluride
  参考文献：
  名称：

  完全控制乙烯基碲化物的区域和立体异构体的合成

  摘要：

  描述了对E，Z或1，1-取代的乙烯基碲化物的合成进行总体控制的方法。还获得在碳2或在碳1上带有丁基或碲构型的碲脲丁二烯，该碲在含碲的双键处具有E或Z构型。在末端炔烃中添加丁基碲铝酸二异丁基铝导致形成1-（丁基teluro）-1-（有机基）乙烯，产率为45％至75％。Al / Te在乙烯基丙氨酸上与丁基碲基溴化物/ LiCl的交换反应以50-60％的收率提供了E构型的异构体。通过乙炔化碲化物的水铝化，可以在30-51％的收率下获得形成双键的Z构型的乙烯基碲化物。

  DOI：

  10.1016/0040-4020(95)00840-5

文献信息

• (1 Z ,3 Z )-Buta-1,3-dienyl-1-lithium species and substituted tellurophenes by Te/Li exchange on (1 Z ,3 Z )-butyltelluro-1,3-butadienes and (1 Z ,3 Z )-1,4-bis(butyltelluro)-1,3-butadienes
  作者：Miguel J. Dabdoub、Vania B. Dabdoub、Palimécio G. Guerrero、Claudio C. Silveira

  DOI：10.1016/s0040-4020(97)00148-8

  日期：1997.3

  (1Z,3Z)-1-Butyltelluro-1,3-butadienes 8, 9 and 12 obtained by the hydrotelluration of but-1-en-3-ynes 1, 2 and 5 were transformed into the corresponding buta-1,3-dienyl-1-lithium by reaction with n-BuLi. 1,3-Butadienes 14, 15, 17-20 were obtained with retention of the double bond geometry by reaction of the butadienyllithium intermediates with electrophiles. The butadienyllithium 13 obtained by the Te/Li exchange reaction in the (12,3Z)-1-Butyltelluro-4-methoxy-1,3-Butadiene 8 was reacted with benzaldehyde to form the corresponding alcohol 15 with total retention of configuration, that undergoes hydrolysis resulting into the (E,E)-5-phenyl-2,3-pentadien-1-al 16. Hydrotelluration of the 1-butyltellurobut-1-en-3-cyclization, leading to substituted tellurophenes 24, 25, 27-29 via a sequential Csp(2)-Te and Csp(3)-Te bonds cleavage on reaction with n-BuLi followed by addition of electrophiles. (C) 1997 Elsevier Science Ltd.

  (1Z,3Z)-1-丁基-1,3-丁二烯碲化物8、9和12是通过1-丁-3-炔-1-烯的水合碲化反应获得的，随后通过与n-BuLi的反应转化为相应的1-丁-1,3-二烯基锂。通过将这些丁二烯基锂中间体与电亲核试剂反应，在保留双键几何构型的情况下，得到了1,3-丁二烯14、15和17-20。通过Te/Li交换反应，在(12,3Z)-4-甲氧基-1-丁基-1,3-丁二烯碲化物8的基础上获得了丁二烯基锂13，并与苯甲醛反应形成了保留全部构型的相应醇15，该醇经水解生成(E,E)-5-苯基-2,3-戊二烯-1-醛16。1-丁基-1-烯-3-炔的水合碲化后，通过与n-BuLi的反应依次断裂Csp(2)-Te和Csp(3)-Te键，随后加入电亲核试剂，形成取代的碲代芳香烃24、25、27-29。 (C) 1997 Elsevier Science Ltd.
• Total control on the synthesis of regio and stereoisomers of vinylic tellurides
  作者：Miguel J. Dabdoub、Tania M. Cassol

  DOI：10.1016/0040-4020(95)00840-5

  日期：1995.11

  Methodologies for the total control on the synthesis of E, Z or 1,1-dissubstituted vinylic tellurides are described. Tellurobutadienes bearing the butyltellurium moiety at carbon 2 or at carbon 1 with E or Z configuration at the tellurium containing double bond were also obtained. Addition of diisobutylaluminum butyltellurolate to terminal alkynes resulted in the formation of 1-(butylteluro)-1-(organyl)

  描述了对E，Z或1，1-取代的乙烯基碲化物的合成进行总体控制的方法。还获得在碳2或在碳1上带有丁基或碲构型的碲脲丁二烯，该碲在含碲的双键处具有E或Z构型。在末端炔烃中添加丁基碲铝酸二异丁基铝导致形成1-（丁基teluro）-1-（有机基）乙烯，产率为45％至75％。Al / Te在乙烯基丙氨酸上与丁基碲基溴化物/ LiCl的交换反应以50-60％的收率提供了E构型的异构体。通过乙炔化碲化物的水铝化，可以在30-51％的收率下获得形成双键的Z构型的乙烯基碲化物。
• Two-Step Regio- and Stereoselective Synthesis of <i>cis</i>-Vinylstannanes
  作者：Paul Malek Mirzayans、Rebecca H. Pouwer、Craig M. Williams

  DOI：10.1021/ol801251m

  日期：2008.9.1

  Herein we describe a novel stereoselective synthesis of cis-vinylstannanes employing the widely established Li/Te exchange pathway. In contrast to previously reported methods of cis-selective hydrostannation (i.e., ZrCl4), this method demonstrates compatibility toward oxygenated substrates.
• Synthesis of 1,3-enynes via Suzuki-type reaction of vinylic tellurides and potassium alkynyltrifluoroborate salts
  作者：Hélio A. Stefani、Rodrigo Cella、Felipe A. Dörr、Claudio M.P. Pereira、Gilson Zeni、Marlito Gomes

  DOI：10.1016/j.tetlet.2004.11.160

  日期：2005.1

  The palladium-catalyzed cross-coupling reaction between potassium alkynyltrifluoroborate salts and vinylic tellurides proceeds readily to afford 1,3-enynes with moderate to good yields. (C) 2004 Elsevier Ltd. All rights reserved.
• Palladium-catalyzed cross-coupling of vinylic tellurides and potassium vinyltrifluoroborate salt: synthesis of 1,3-dienes
  作者：Rodrigo Cella、Aline T.G. Orfão、Hélio A. Stefani

  DOI：10.1016/j.tetlet.2006.05.088

  日期：2006.7

  Here we report an ultrasound-assisted synthesis of stereodefined 1,3-dienes by Suzuki-Miyaura cross-coupling reactions of vinylic tellurides and potassium beta-styryl trifluoroborate salt. (c) 2006 Elsevier Ltd. All rights reserved.