1r,2c-bis-(4-chloro-phenyl)-1,2t-diphenyl-ethene | 101634-82-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 1r,2c-bis-(4-chloro-phenyl)-1,2t-diphenyl-ethene
• 英文别名: 1r,2c-Bis-(4-chlor-phenyl)-1,2t-diphenyl-aethen；cis-1.2-Diphenyl-1.2-bis-(4-chlor-phenyl)-aethylen；cis-1,2-Bis-(4-chlor-phenyl)-1,2-diphenyl-ethylen；cis-1,2-Bis-(p-chlorphenyl)-1,2-diphenyl-ethylen；1-chloro-4-[(Z)-2-(4-chlorophenyl)-1,2-diphenylethenyl]benzene
• CAS: 101634-82-6
• 化学式: C₂₆H₁₈Cl₂
• 分子量: 401.335
• InChiKey: JLHQIDAYNIYCQY-QPLCGJKRSA-N

物化性质

• 熔点：
  202-203 °C
• 沸点：
  474.8±40.0 °C(Predicted)
• 密度：
  1.218±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  9.2
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 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：

  1r,2c-bis-(4-chloro-phenyl)-1,2t-diphenyl-ethene 、 溴 、 碘 生成 alkaline earth salt of/the/ methylsulfuric acid
  参考文献：
  名称：

  Bockemueller; Janssen, Justus Liebigs Annalen der Chemie, 1939, vol. 542, p. 166,182

  摘要：

  DOI：
• 作为产物：
  描述：

  [(4-氯苯基)苯基亚甲基]三苯基正膦 在 selenium 作用下， 以 甲苯 为溶剂， 25.0~75.0 ℃ 、1200.0 MPa 条件下， 反应 24.0h， 生成 1r,2c-bis-(4-chloro-phenyl)-1,2t-diphenyl-ethene
  参考文献：
  名称：

  Stereochemistry of the [4 + 2] Cycloaddition of Diarylselenoketones with Conjugated Dienes

  摘要：

  The ylides Ph(3)P=(CArAr2)-Ar-1 1a-g (Ar C6H5, p-C6H4Cl p-C6H4F, m-C6H4CF3, P-C(6)H4OCH(3), p-C6H4CH3) were treated with elemental selenium (similar to 80 degrees C) to give the corresponding selenoketones Se=CAr(1)Ar2 2 by Staudinger-chalcogenation. Their reaction with trans,trans-2,4-hexadiene proceeds completely stereospecifically to yield the 2,2-diaryl-3,6-dihydro-cis-3,6-dimethyl-2H-selenapyrans 3. In contrast, the reactions of the selenoketones 2 with cis, trans-2,4-hexadiene proceeds stereoselectively, also giving the dihydro-cis-dimethyl-2H-selenapyrans 3 as the major products, now admired with small amounts of the dihydro-trans-dimethyl-2H-selenapyran isomers 4. The [4 + 2] cydoaddition of 2 with cis,trans-2,4-hexadiene proceeds stereospecifically, however, when carried out at a pressure of 12 kbar, now yielding 4 as the major products along with the corresponding tetraarylethenes 8. Along with the results of additional mechanistic studies (determination of solvent and substituent effects) it can be concluded that diarylselenoketones are likely to react by means of a concerted [4 + 2] cycloaddition with very reactive conjugated dienes (such as trans,trans-2,4-hexadiene), whereas a stepwise mechanism, resulting in diene cis/trans-isomerization with subsequent mechanistic ''leakage'' to the concerted pathway, appears to be preferred when a much less reactive conjugated diene such as cis,trans-2,4-hexadiene is employed. The reaction of the corresponding diarylthioketones 5a-g with trans,trans- and cis,trans-2,4-hexadiene, respectively, shows an analogous behavior.

  DOI：

  10.1021/ja00149a015

文献信息

• A Novel Diarylation Reaction of Alkynes by Using Aryltributylstannane in the Presence of Palladium Catalyst
  作者：Hiroshi Oda、Michiko Morishita、Keigo Fugami、Hiroshi Sano、Masanori Kosugi

  DOI：10.1246/cl.1996.811

  日期：1996.9

  Some alkynes were diarylated by aryltributylstannane 2 in the presence of palladium salt in moderate to good yield with high stereoselectivity. The reaction was catalytic in palladium using copper(II) chloride dihydrate as a reoxidant.

  在钯盐存在下，芳基三丁基锡烷 2 对一些炔烃进行了二芳基化反应，收率从中等到良好，并具有很高的立体选择性。该反应以二水氯化铜（II）为还原剂，在钯中催化进行。
• The Interaction of Bromine with Substituted Tetraphenylethylenes¹
  作者：Robert E. Buckles、Norman A. Meinhardt

  DOI：10.1021/ja01125a011

  日期：1952.3
• Stereochemistry of the [4 + 2] Cycloaddition of Diarylselenoketones with Conjugated Dienes
  作者：Stefanie Wilker、Gerhard Erker

  DOI：10.1021/ja00149a015

  日期：1995.11

  The ylides Ph(3)P=(CArAr2)-Ar-1 1a-g (Ar C6H5, p-C6H4Cl p-C6H4F, m-C6H4CF3, P-C(6)H4OCH(3), p-C6H4CH3) were treated with elemental selenium (similar to 80 degrees C) to give the corresponding selenoketones Se=CAr(1)Ar2 2 by Staudinger-chalcogenation. Their reaction with trans,trans-2,4-hexadiene proceeds completely stereospecifically to yield the 2,2-diaryl-3,6-dihydro-cis-3,6-dimethyl-2H-selenapyrans 3. In contrast, the reactions of the selenoketones 2 with cis, trans-2,4-hexadiene proceeds stereoselectively, also giving the dihydro-cis-dimethyl-2H-selenapyrans 3 as the major products, now admired with small amounts of the dihydro-trans-dimethyl-2H-selenapyran isomers 4. The [4 + 2] cydoaddition of 2 with cis,trans-2,4-hexadiene proceeds stereospecifically, however, when carried out at a pressure of 12 kbar, now yielding 4 as the major products along with the corresponding tetraarylethenes 8. Along with the results of additional mechanistic studies (determination of solvent and substituent effects) it can be concluded that diarylselenoketones are likely to react by means of a concerted [4 + 2] cycloaddition with very reactive conjugated dienes (such as trans,trans-2,4-hexadiene), whereas a stepwise mechanism, resulting in diene cis/trans-isomerization with subsequent mechanistic ''leakage'' to the concerted pathway, appears to be preferred when a much less reactive conjugated diene such as cis,trans-2,4-hexadiene is employed. The reaction of the corresponding diarylthioketones 5a-g with trans,trans- and cis,trans-2,4-hexadiene, respectively, shows an analogous behavior.
• Bockemueller; Janssen, Justus Liebigs Annalen der Chemie, 1939, vol. 542, p. 166,182
  作者：Bockemueller、Janssen

  DOI：——

  日期：——