cis,exo 5-i-propyl-1,2,3,4,4a,8b-hexahydro-1,4-methanobiphenylene

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: cis,exo 5-i-propyl-1,2,3,4,4a,8b-hexahydro-1,4-methanobiphenylene
• 英文别名: (1S,2R,9S,10R)-4-propan-2-yltetracyclo[8.2.1.02,9.03,8]trideca-3(8),4,6-triene
• 化学式: C₁₆H₂₀
• 分子量: 212.335
• InChiKey: ZCHIJVUCYWDABH-BAESOJJISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  降冰片烯 、 2-碘异丙基苯 在 palladium diacetate 、 2-碘异丙基苯 、 potassium acetate 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 72.0h， 以24%的产率得到cis,exo 5-i-propyl-1,2,3,4,4a,8b-hexahydro-1,4-methanobiphenylene
  参考文献：
  名称：

  A catalytic process based on sequential ortho-alkylation and vinylation of ortho-alkylaryl iodides via palladacycles

  摘要：

  A new synthesis of vinylarenes selectively substituted in both their ortho positions with different alkyl groups is reported The reaction occurs starting from ortho-alkyl substituted iodoarenes which are caused to react with aliphatic iodides, terminal olefins, K2CO3, AcOK and Pd(OAc)(2) in a one-pot reaction consisting of a series of elementary steps controlled by palladium in its oxidation stales 0, II and IV. A correct balance of all the steps involved is required to obtain a catalytic reaction. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00293-8

文献信息

• Palladium-catalysed synthesis of nonsymmetrically disubstituted-1,1′-biphenyls from <i>o</i>-substituted aryl iodides through aryl coupling and delayed hydrogenolysis
  作者：Sara Deledda、Elena Motti、Marta Catellani

  DOI：10.1139/v05-084

  日期：2005.6.1

  In the presence of Pd(OAc)₂ and norbornene as catalysts, two molecules of an ortho-substituted aryl iodide undergo aryl–aryl coupling to a palladium-bonded biphenylyl intermediate, which is hydrogenolyzed by benzyl alcohol to give 2,3′-disubstituted biaryl derivatives in satisfactory yields. A curious behaviour was observed with o-chloroiodobenzene, which gave activation of the C—Cl bond with four-membered ring formation.Key words: biphenyls, aryl–aryl coupling, multistep reactions, palladium, palladacycles, C-H activation, catalysis.

  在Pd(OAc)₂和诺伯烯的催化下，两分子的邻位取代芳基碘发生芳基-芳基偶联反应，生成与钯键合的联苯基中间体，通过苄醇的加氢解除钯键，得到2,3'-二取代联苯衍生物，收率满意。对于o-氯碘苯观察到了一种奇特的行为，即C-Cl键被激活形成了四元环。关键词：联苯，芳基-芳基偶联，多步反应，钯，钯杂环化合物，C-H键活化，催化。
• Synthesis of Selectively Substituted<i>ortho</i>-Vinylbiphenyls by Palladium-Catalysed Reaction of<i>ortho</i>-Substituted Aryl Iodides with Olefins
  作者：Marta Catellani、Elena Motti、Gianpietro Ippomei、Sara Deledda

  DOI：10.1055/s-2003-42441

  日期：——

  In the presence of Pd(OAc) 2 and norbornene as catalysts, ortho-substituted aryl iodides and terminal olefins react to afford selectively substituted ortho-vinylbiphenyl derivatives in good yields. The reaction proceeds through a series of steps including norbornene insertion and C-H activation with formation of pallada-cycles able to promote arylation of their aromatic part. Norbornene deinsertion

  在 Pd(OAc) 2 和降冰片烯作为催化剂的存在下，邻位取代的芳基碘化物和末端烯烃反应以良好的收率得到选择性取代的邻位乙烯基联苯衍生物。该反应通过一系列步骤进行，包括降冰片烯插入和 CH 活化，形成能够促进其芳族部分芳基化的钯环。然后降冰片烯脱嵌导致选择性形成能够与末端烯烃反应的钯键合联苯基。