4-promppentacyclo[7.3.0.0^2,7.0^3,11.0^6,10]dodec-11ene | 210285-78-2

• 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: 4-promppentacyclo[7.3.0.0^2,7.0^3,11.0^6,10]dodec-11ene
• 英文别名: 4-bromo[2.1.1]triblattene；11-Bromopentacyclo[6.4.0.02,6.03,10.05,9]dodec-11-ene；11-bromopentacyclo[6.4.0.02,6.03,10.05,9]dodec-11-ene
• CAS: 210285-78-2
• 化学式: C₁₂H₁₃Br
• 分子量: 237.139
• InChiKey: LUOQSDVPTFNSIB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.83
• 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：

  4-promppentacyclo[7.3.0.0^2,7.0^3,11.0^6,10]dodec-11ene 在 溴 作用下， 以 四氯化碳 为溶剂， 反应 1.0h， 以94%的产率得到4,4,5-tribromopentacyclo[7.3.0.0^2,7.0^3,11.0^6,10]dodecane
  参考文献：
  名称：

  摘要：

  Reaction of 4-bromopentacyclo[7.3.0.0(2.7).0(3,11).0(6,10)]dodec-11-ene (1) With Br-2- CCl4 afforded 4,4,5 -tribromopentacyclo [7.3.0.0(2,7).0(3,11).0(6,10)]dodecane (2) in 89-94% yield. Subsequent treatment of 2 with KOt-Bu-t-BuOH resulted in competitive elimination of the elements of HBr and of Br-2 with concomitant formation of 4,5-dibromopentacyclo[7.3.0.0(2,7).0(3,11),0(6,10)]dodec-11-ene (3, 76%) and 1 (17%), respectively. The structure of 3 was established unequivocally via application of X-ray crystallographic methods. Crystal data for 3: monoclinic, C2/c, a = 9.895(1), b = 9.0963(7), c = 12.471(1) Angstrom, beta = 106.875(8)degrees, z = 4.

  DOI：

  10.1023/a:1009538321507
• 作为产物：
  描述：

  C₁₂H₁₆N₂ 在 三乙胺 、 copper(ll) bromide 作用下， 以 甲醇 为溶剂， 反应 4.0h， 以73%的产率得到4-promppentacyclo[7.3.0.0^2,7.0^3,11.0^6,10]dodec-11ene
  参考文献：
  名称：

  Study of a Vinylidenecarbene−Cycloalkyne Equilibrium in the D₃-Trishomocubyl Ring System

  摘要：

  The same cage-annulated vinylidenecarbene, 7a, could be generated and subsequently trapped in situ by cyclohexene via either of the following methods: (i) low-temperature reaction of 4-(dibromomethylene)pentacyclo[6.3.0.0(2,6).0(3,10).0(5,9)]undecane (6) with n-BuLi-THF and (ii) low-temperature reaction of 5-bromopentacyclo[7.3.0.0(2,6).0(3,10).0(5,9)]dodec-4-ene (12) with LDA-THF. These results, together with the corresponding results of site-specific C-13-labeling experiments performed on 6-(C) over bar(4)=(CBr2)-C-13 and 12-C-13(5), provide evidence for the thermodynamic stability of 7a vis-h-vis 7b. In addition, the results of semiempirical and ab initio MO calculations demonstrate the relative kinetic as well as thermodynamic preference for 7a vis-a-vis 7b.

  DOI：

  10.1021/ja974313e

文献信息

• Study of a Vinylidenecarbene−Cycloalkyne Equilibrium in the <i>D</i>₃-Trishomocubyl Ring System
  作者：Alan P. Marchand、I. N. N. Namboothiri、Bishwajit Ganguly、Simon G. Bott

  DOI：10.1021/ja974313e

  日期：1998.7.1

  The same cage-annulated vinylidenecarbene, 7a, could be generated and subsequently trapped in situ by cyclohexene via either of the following methods: (i) low-temperature reaction of 4-(dibromomethylene)pentacyclo[6.3.0.0(2,6).0(3,10).0(5,9)]undecane (6) with n-BuLi-THF and (ii) low-temperature reaction of 5-bromopentacyclo[7.3.0.0(2,6).0(3,10).0(5,9)]dodec-4-ene (12) with LDA-THF. These results, together with the corresponding results of site-specific C-13-labeling experiments performed on 6-(C) over bar(4)=(CBr2)-C-13 and 12-C-13(5), provide evidence for the thermodynamic stability of 7a vis-h-vis 7b. In addition, the results of semiempirical and ab initio MO calculations demonstrate the relative kinetic as well as thermodynamic preference for 7a vis-a-vis 7b.
• ——
  作者：Simon G. Bott、Alan P. Marchand、I. N. N. Namboothiri

  DOI：10.1023/a:1009538321507

  日期：——

  Reaction of 4-bromopentacyclo[7.3.0.0(2.7).0(3,11).0(6,10)]dodec-11-ene (1) With Br-2- CCl4 afforded 4,4,5 -tribromopentacyclo [7.3.0.0(2,7).0(3,11).0(6,10)]dodecane (2) in 89-94% yield. Subsequent treatment of 2 with KOt-Bu-t-BuOH resulted in competitive elimination of the elements of HBr and of Br-2 with concomitant formation of 4,5-dibromopentacyclo[7.3.0.0(2,7).0(3,11),0(6,10)]dodec-11-ene (3, 76%) and 1 (17%), respectively. The structure of 3 was established unequivocally via application of X-ray crystallographic methods. Crystal data for 3: monoclinic, C2/c, a = 9.895(1), b = 9.0963(7), c = 12.471(1) Angstrom, beta = 106.875(8)degrees, z = 4.