deca-(Z,E)-1,7,9-trienyl iodide | 147137-07-3

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 乙烯基卤化物
• 英文名称: deca-(Z,E)-1,7,9-trienyl iodide
• 英文别名: (3E,9Z)-10-iododeca-1,3,9-triene
• CAS: 147137-07-3
• 化学式: C₁₀H₁₅I
• 分子量: 262.134
• InChiKey: WCCNYKGPPZBRCT-YKNGABIKSA-N

物化性质

• 沸点：
  254.2±19.0 °C(predicted)
• 密度：
  1.345±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  11
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.4
• 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：

  deca-(Z,E)-1,7,9-trienyl iodide 、 triphenylphosphine tungsten pentacarbonyl 以53%的产率得到
  参考文献：
  名称：

  Wilff William D., Powers Timothy S., J. Org. Chem., 58 (1993) N 9, S 2381- 2393

  摘要：

  DOI：
• 作为产物：
  描述：

  (E)-6,8-nonadienol 在 chromium dichloride 、 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 3.75h， 生成 deca-(Z,E)-1,7,9-trienyl iodide
  参考文献：
  名称：

  Stereochemical control in intramolecular Diels-Alder reactions with carbene complexes as ester synthons

  摘要：

  An evaluation of the intramolecular Diels-Alder reactions of Fischer carbene complexes was made for complexes which have an all-carbon tether between the diene and dienophile. Specifically, both the cis- and trans-isomers of the deca-2,7,9-trienyl carbene complexes (26-cis, 24-trans) and the undeca-2,8,10-trienyl carbene complexes (27-cis, 25-trans) were prepared and the rates and stereoselectivities of their intramolecular Diels-Alder reactions were in each case compared with those of the known reactions of their corresponding methyl esters. For the deca-2,7,9-trienyl complexes 24 and 26, the stereoselectivities are comparable to those observed for the Lewis-acid-catalyzed reactions of their corresponding methyl esters and much higher than the thermal reactions of the methyl esters which are completely unselective. The undeca-2,8,10-trienyl complex 25 undergoes intramolecular Diels-Alder reaction with a 93:7 endo/exo selectivity whereas the corresponding methyl ester 7 is known to give a 51:49 selectivity under thermal conditions and to fail with attempts at Lewis acid catalysis. The cis-substituted complex 27 also undergoes a selective reaction where the corresponding reaction of the ester fails. In addition no trace of isomerization of the cis-complex 27 could be observed during its cycloaddition. The triphenylphosphine and isopropoxy complexes 28-30 were prepared, and the stereoselectivity of their intramolecular Diels-Alder reactions is consistent with an s-trans conformation of the vinyl carbene funtionality in the transition state. In all cases the carbene complex cycloadducts can be oxidatively cleaved in high yield to their corresponding esters. The results show that the value of these complexes as synthons for esters is a result of tolerance of the carbene complex functional group to sensitive diene units which do not tolerate traditional Lewis acids utilized in accelerating intramolecular Diels-Alder reactions.

  DOI：

  10.1021/jo00061a008

文献信息

• Stereochemical control in intramolecular Diels-Alder reactions with carbene complexes as ester synthons
  作者：William D. Wulff、Timothy S. Powers

  DOI：10.1021/jo00061a008

  日期：1993.4

  An evaluation of the intramolecular Diels-Alder reactions of Fischer carbene complexes was made for complexes which have an all-carbon tether between the diene and dienophile. Specifically, both the cis- and trans-isomers of the deca-2,7,9-trienyl carbene complexes (26-cis, 24-trans) and the undeca-2,8,10-trienyl carbene complexes (27-cis, 25-trans) were prepared and the rates and stereoselectivities of their intramolecular Diels-Alder reactions were in each case compared with those of the known reactions of their corresponding methyl esters. For the deca-2,7,9-trienyl complexes 24 and 26, the stereoselectivities are comparable to those observed for the Lewis-acid-catalyzed reactions of their corresponding methyl esters and much higher than the thermal reactions of the methyl esters which are completely unselective. The undeca-2,8,10-trienyl complex 25 undergoes intramolecular Diels-Alder reaction with a 93:7 endo/exo selectivity whereas the corresponding methyl ester 7 is known to give a 51:49 selectivity under thermal conditions and to fail with attempts at Lewis acid catalysis. The cis-substituted complex 27 also undergoes a selective reaction where the corresponding reaction of the ester fails. In addition no trace of isomerization of the cis-complex 27 could be observed during its cycloaddition. The triphenylphosphine and isopropoxy complexes 28-30 were prepared, and the stereoselectivity of their intramolecular Diels-Alder reactions is consistent with an s-trans conformation of the vinyl carbene funtionality in the transition state. In all cases the carbene complex cycloadducts can be oxidatively cleaved in high yield to their corresponding esters. The results show that the value of these complexes as synthons for esters is a result of tolerance of the carbene complex functional group to sensitive diene units which do not tolerate traditional Lewis acids utilized in accelerating intramolecular Diels-Alder reactions.
• Wilff William D., Powers Timothy S., J. Org. Chem., 58 (1993) N 9, S 2381- 2393
  作者：Wilff William D., Powers Timothy S.

  DOI：——

  日期：——