(Z,E)-5-[(tetrahydropyranyl)oxy]-1,3-pentadienyl-1-butyl telluride | 173442-07-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: (Z,E)-5-[(tetrahydropyranyl)oxy]-1,3-pentadienyl-1-butyl telluride
• 英文别名: 2-[(2E,4Z)-5-butyltellanylpenta-2,4-dienoxy]oxane
• CAS: 173442-07-4
• 化学式: C₁₄H₂₄O₂Te
• 分子量: 351.943
• InChiKey: GYRAQXSJXPSUNG-GVVZRPPFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.52
• 重原子数：
  17
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-戊炔-1-醇 、 (Z,E)-5-[(tetrahydropyranyl)oxy]-1,3-pentadienyl-1-butyl telluride 在 copper(l) iodide 、 palladium dichloride 三乙胺 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以78%的产率得到(6Z,8E)-10-(Tetrahydro-pyran-2-yloxy)-deca-6,8-dien-4-yn-1-ol
  参考文献：
  名称：

  Coupling of Z-vinylic tellurides with alkynes catalysed by : synthesis of Z-enynes and Z-enediynes

  摘要：

  Vinylic tellurides of the Z-configuration couple with alkynes under PdCl2/CuI catalysis to give enynes and enediynes in good yields and with retention of the double bond configuration. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)00773-x
• 作为产物：
  描述：

  二丁基二碲 、 (E)-5-(tetrahydropyran-2-yloxy)pent-3-en-1-yne 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以80%的产率得到(Z,E)-5-[(tetrahydropyranyl)oxy]-1,3-pentadienyl-1-butyl telluride
  参考文献：
  名称：

  （-）-Macactactin F C7–C24片段的合成

  摘要：

  从四个主要片段完成了对Macrolactin F的C7–C24片段的对映选择性和聚合反应的合成。使用氢加氢除盐/重金属化序列来安装分子中存在的E，Z二烯，而使用加氢锆化/重金属化序列来连接两个高级中间体。

  DOI：

  10.1016/j.tetlet.2008.07.113

文献信息

• Addition of Z-Vinylic Higher Order Cyanocuprates to Enones Followed by O-Functionalization
  作者：D.N. Moraes、R.E. Barrientos-Astigarraga、P. Castelani、J.V. Comasseto

  DOI：10.1016/s0040-4020(00)00254-4

  日期：2000.5

  Transmetalation reaction between Z-vinylic tellurides and higher order cyanocuprates generated the corresponding Z-vinylic cyanocuprates. Conjugate addition of these cuprates to enones followed by O-functionalization led to silyl enol ethers, vinyl phosphates and vinyl triflates. The vinyl triflates were transformed into highly unsaturated systems by coupling with alkynes or with Z-vinyl zinc chlorides

  Z-乙烯基碲化物和高阶氰基铜酸盐之间的金属转移反应生成了相应的Z-乙烯基氰基铜酸盐。将这些铜酸盐共轭加入烯酮中，然后进行O-官能化，生成甲硅烷基烯醇醚，磷酸乙烯基酯和乙烯基三氟甲磺酸酯。在Pd（0）催化下，通过与炔烃或Z-乙烯基锌氯化物偶联，将乙烯基三氟甲磺酸酯转化为高度不饱和的体系。
• 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.
• Coupling of Z-vinylic tellurides with alkynes catalysed by : synthesis of Z-enynes and Z-enediynes
  作者：Gilson Zeni、João V. Comasseto

  DOI：10.1016/s0040-4039(99)00773-x

  日期：1999.6

  Vinylic tellurides of the Z-configuration couple with alkynes under PdCl2/CuI catalysis to give enynes and enediynes in good yields and with retention of the double bond configuration. (C) 1999 Elsevier Science Ltd. All rights reserved.
• Synthesis of the C7–C24 fragment of (−)-Macrolactin F
  作者：Roberta A. Oliveira、Juliana M. Oliveira、Luis H.S. Rahmeier、Joao V. Comasseto、Joseph P. Marino、Paulo H. Menezes

  DOI：10.1016/j.tetlet.2008.07.113

  日期：2008.9

  An enantioselective and convergent synthesis of the C7–C24 fragment of Macrolactin F was achieved from four main fragments. A hydrotelluration/transmetalation sequence was used to install the E,Z diene present in the molecule, while a hydrozirconation/transmetalation sequence was used to connect two advanced intermediates.

  从四个主要片段完成了对Macrolactin F的C7–C24片段的对映选择性和聚合反应的合成。使用氢加氢除盐/重金属化序列来安装分子中存在的E，Z二烯，而使用加氢锆化/重金属化序列来连接两个高级中间体。