2-n-Butylbicyclo<2.2.1>hepta-2,5-dien | 86660-97-1

• 分子结构分类: 有机化合物 - 碳氢化合物 - 不饱和烃
• 英文名称: 2-n-Butylbicyclo<2.2.1>hepta-2,5-dien
• 英文别名: 2-butylnorbornadiene；2-Butylbicyclo[2.2.1]hepta-2,5-diene
• CAS: 86660-97-1
• 化学式: C₁₁H₁₆
• 分子量: 148.248
• InChiKey: RRPMRBRLPCXFBC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.64
• 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：

  1-n-butyltetracyclo<3.2.0.0^2.7.0^4.6>heptane 在 di-μ-chlorobis(norbornadiene)dirhodium(I) 作用下， 反应 5.0h， 以78%的产率得到2-n-Butylbicyclo<2.2.1>hepta-2,5-dien
  参考文献：
  名称：

  Baumgaertel, Otto; Szeimies, Guenter, Chemische Berichte, 1983, vol. 116, # 6, p. 2180 - 2204

  摘要：

  DOI：

文献信息

• Polymers containing ring-strain energy. 1. New monomers and polymers based on cyclopropane, norbornadiene, and quadricyclane
  作者：Michael E. Wright、Gary D. Allred、Robert B. Wardle、Louis F. Cannizzo

  DOI：10.1021/jo00067a055

  日期：1993.7

  The synthesis and polymerization chemistry of 1,1-bis(XCH2)cyclopropane 1, X = OH; 4, X = I} was studied. Treatment of 1 with base in the presence of alpha,omega-dihalides did not produce a polyether. However, treatment of 4 with the bis(alkoxide) derived from hexanediol afforded a polyether of low molecular weight M(n) = 3000, PD = 3}. A general method for alkylating norbornadiene in the 2-position was developed. Treatment of norbornadiene with tert-BuOK, tetramethylethylenediamine (TMEDA), n-BuLi, and tributylchloroetannane (in that order) afforded 2-(tributylstannyl)norbornadiene in excellent yield. On the other hand, carbon electrophiles eg. bromobutane, 1,4-dibromobutane, and 2,3-dichloropropene} required the generation of the 2-(lithiocyanocuprate) in order to effect clean alkylation. Treatment of 2-[3-(2-chloropropenyl)]norbornadiene (8a) with RMgX where R = vinyl and phenyl} in the presence of (dppp)NiCl2 afforded the cross-coupling products 2-(XCH2)-norbornadiene 9, X = 2-buta-1,3-dienyl; 10, X = alpha-styryl; respectively} in high yield. Polymerization of 9 in THF initiated by n-BuLi resulted in an elastomeric polymer (12) [M(n) = 18,000, PD = 1.5]. Photolysis of 12 in the presence of (Ph3P)2CuBr converted the pendant norbornadiene to quadricyclane (13). Heating of the photoisomerized sample to 180-degrees-C caused an exothermic (by DSC) reaction which corresponded to 59% of theory (using the value 26 kcal/mol: quadricyclane --> norbornadiene).
• Baumgaertel, Otto; Szeimies, Guenter, Chemische Berichte, 1983, vol. 116, # 6, p. 2180 - 2204
  作者：Baumgaertel, Otto、Szeimies, Guenter

  DOI：——

  日期：——