(1R,1'R)-2-(1,7,7-trimethylbicyclo[2.2.1]hept-2-en-3-yl)-1,7,7-trimethylbicyclo[2.2.1]hept-2-ene

• 分子结构分类: 有机化合物 - 碳氢化合物 - 多环烃
• 英文名称: (1R,1'R)-2-(1,7,7-trimethylbicyclo[2.2.1]hept-2-en-3-yl)-1,7,7-trimethylbicyclo[2.2.1]hept-2-ene
• 英文别名: (1R,4'R,1'R,4R)-1,1',7,7,7',7'-hexamethyl-2,2'-bi(bicyclo[2.2.1]hept-2-ene)；(1R,4R)-1,7,7-trimethyl-2-[(1R,4R)-1,7,7-trimethyl-2-bicyclo[2.2.1]hept-2-enyl]bicyclo[2.2.1]hept-2-ene
• 化学式: C₂₀H₃₀
• 分子量: 270.458
• InChiKey: ROSSNGYPFSUAKE-NSMLZSOPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.8
• 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：

  2-iodobornene 在 copper(l) iodide 、 叔丁基锂 作用下， 以 四氢呋喃 、 正戊烷 为溶剂， 反应 72.0h， 以85%的产率得到(1R,1'R)-2-(1,7,7-trimethylbicyclo[2.2.1]hept-2-en-3-yl)-1,7,7-trimethylbicyclo[2.2.1]hept-2-ene
  参考文献：
  名称：

  衍生自 (+)-樟脑、(+)-苯甲酚酮和 (-)-表樟脑的对映脲-溴（三甲基甲锡烷基）双环烯烃的比较环三聚反应：桥头甲基基团对合成/抗产物比率的影响

  摘要：

  研究了桥头甲基对多环烯烃环三聚反应中顺/反非对映选择性的影响。为此，制备了三种不同的对映体纯 vic-bromo(trimethylstannyl)-取代的双环烯烃并用作探针。研究了不同铜 (II) 或 -(I) 盐的影响，并且大多数二聚中间体是独立合成和表征的。环三聚机制的一些迹象是通过旨在确定二聚的相对速率的实验提供的。结果为如何实现高效的顺式环三聚反应提供了有用的指示。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)

  DOI：

  10.1002/ejoc.200400120

文献信息

• Heck self-condensation of polycyclic haloalkenes: the case of (1R)-2-iodobornene
  作者：Laura Zambrini、Fabrizio Fabris、Ottorino De Lucchi、Graziano Gardenal、Fabiano Visentin、Luciano Canovese

  DOI：10.1016/s0040-4020(01)00850-x

  日期：2001.10

  The unusual reactivity of a haloalkene undergoing Heck reaction behaving both as reagent and substrate (Heck donor and acceptor) is studied and discussed in detail in the case of (1R)-2-iodo-1,7,7-trimethyl-bicyclo[2.2.1]hept-2-ene (2-iodobornene). This enantiopure substrate allows for a rational description of the mechanism which takes into account the nature of the products and the substitution of one of the substituents (iodine and proton) at carbons 2 and 3 of the bornene skeleton. Under catalytic conditions the main products are the syn and anti-cyclotrimers, a head-to-tail dimer and an arene derived from the latter. The products of the stoichiometric reaction between palladium(0) tetrakis(triphenylphosphine) and 2-iodobornene are principally trans-Pd(PPh3)(2)PhI and various dimeric species. The results are rationalized in terms of a catalytic reaction which takes into account the Pd(H)-Pd(IV) oxidation state sequence. The major products in both the catalytic and stoichiometric reactions are dimeric species with formal elimination of an iodine molecule that are unprecedented in the literature for the Heck reaction. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Comparative Cyclotrimerisation of Enantiopurevic-Bromo(trimethylstannyl)bicycloalkenes Derived from (+)-Camphor, (+)-Fenchocamphorone and (−)-Epicamphor: Effect of the Bridgehead Methyl Group on thesyn/anti Product Ratios
  作者：Fabrizio Fabris、Laura Zambrini、Enrico Rosso、Ottorino De Lucchi

  DOI：10.1002/ejoc.200400120

  日期：2004.8

  The influence of the bridgehead methyl group on syn/anti diastereoselectivity in the cyclotrimerisation of polycyclic alkenes was investigated. To this end, three different enantiopure vic-bromo(trimethylstannyl)-substituted bicyclic olefins were prepared and used as probes. The effects of different copper(II) or -(I) salts were studied, and most dimeric intermediates were independently synthesised

  研究了桥头甲基对多环烯烃环三聚反应中顺/反非对映选择性的影响。为此，制备了三种不同的对映体纯 vic-bromo(trimethylstannyl)-取代的双环烯烃并用作探针。研究了不同铜 (II) 或 -(I) 盐的影响，并且大多数二聚中间体是独立合成和表征的。环三聚机制的一些迹象是通过旨在确定二聚的相对速率的实验提供的。结果为如何实现高效的顺式环三聚反应提供了有用的指示。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)