(1R,4S,5R,8S)-2,3,4,6,7,8-hexahydro-1,5,11,11',12,12'-hexamethyl-1,4;5,8-dimethanophenanthrene

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: (1R,4S,5R,8S)-2,3,4,6,7,8-hexahydro-1,5,11,11',12,12'-hexamethyl-1,4;5,8-dimethanophenanthrene
• 化学式: C₂₂H₃₀
• 分子量: 294.48
• InChiKey: DDYVFMPXZVPZCH-SDVFQCAASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.04
• 重原子数：
  22.0
• 可旋转键数：
  0.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  0.0

反应信息

• 作为产物：
  描述：

  N,N-二异丙基乙胺 、 2-iodobornene 在 palladium diacetate 4 A molecular sieve 、 n-Bu₄Br 、 三苯基膦 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 以33%的产率得到(1R,4S,5R,8S)-2,3,4,6,7,8-hexahydro-1,5,11,11',12,12'-hexamethyl-1,4;5,8-dimethanophenanthrene
  参考文献：
  名称：

  Heck self-condensation of polycyclic haloalkenes: the case of (1R)-2-iodobornene

  摘要：

  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.

  DOI：

  10.1016/s0040-4020(01)00850-x

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.