tricyclo<3,2,0,0^2,7>heptane | 279-18-5

• 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: tricyclo<3,2,0,0^2,7>heptane
• 英文别名: tricyclo<3.2.0.0^2,7>heptane；Tricyclo<3.2.0.0^2,7>heptan；pseudonortricyclene；Tricyclo<4.1.0.0^3,7>heptan；Tricyclo[3.2.0.02,7]heptane
• CAS: 279-18-5
• 化学式: C₇H₁₀
• 分子量: 94.1564
• InChiKey: YDOHPBBLOFQPQE-UHFFFAOYSA-N

物化性质

• 沸点：
  108.7±7.0 °C(Predicted)
• 密度：
  1.091±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  7
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 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：

  tricyclo<3,2,0,0^2,7>heptane 在 palladium on activated charcoal 氢气 作用下， 以 异辛烷 为溶剂， 以100%的产率得到降莰烷
  参考文献：
  名称：

  降冰片烷。第21部分。降冰片基和氧杂冰片基阳离子中的架桥应变†

  摘要：

  进一步的证据表明，2-降冰片基阳离子主要通过C（2）–C（6）桥接而稳定，而C（2）–C（7）桥接导致抑制性应变。因此，比较了三环戊二烯17和双环的氢化热[3。2. 0. 0. 2.7 ]庚烷18指示后者的应变能是大约21.5更高千卡/摩尔的是那个的17。此外，6 - exo -2--2-氧杂双环[2。2. 1]庚基磺酸盐8与强O（2）参与电离，生成桥连的氧鎓离子12。相反，2-内-7氧杂双环[2.2.1]庚基磺酸盐11在没有O（7）参与的情况下电离，形成未桥连的碳正离子15。

  DOI：

  10.1002/hlca.19880710512
• 作为产物：
  描述：

  2,3-二氮杂三环[4.3.0.04,9]壬-2-烯 在 tri-pyridin-2-yl-[1,3,5]triazine 作用下， 以 二氯甲烷 为溶剂， 以100%的产率得到tricyclo<3,2,0,0^2,7>heptane
  参考文献：
  名称：

  Wagner-Meerwein rearrangements of radical cations generated by triphenylpyrylium tetrafluoroborate photosensitized electron transfer of azoalkanes

  摘要：

  DOI：

  10.1021/ja00239a048

文献信息

• Kirmse, Wolfgang; Siegfried, Rainer; Wroblowsky, Heinz-Juergen, Chemische Berichte, 1983, vol. 116, # 5, p. 1880 - 1896
  作者：Kirmse, Wolfgang、Siegfried, Rainer、Wroblowsky, Heinz-Juergen

  DOI：——

  日期：——
• The 185-nm photolysis and pyrolysis of the spirocyclopropane-substituted azoalkanes of 2,3-diazatricyclo[4.3.0.04,9]non-2-ene and their denitrogenated hydrocarbon products, the tricyclo[3.2.0.02,7]heptanes
  作者：Waldemar Adam、Gerald Zang

  DOI：10.1021/jo00010a026

  日期：1991.5

  The 185-nm photolysis and pyrolysis of the spirocyclopropane derivatives of the azoalkanes 2,3-diazatricyclo[4.3.0.0(4,9)]non-2-ene (1a), 4',5'-diazaspiro(cyclopropane-1,8'-tricyclo[4.3.0.0(3,7)]non-4'-ene) (1b), and 4'5'-diazadispiro(cyclopropane-1,2'-tricyclo[4.3.0.0(3,7)]non-4'-ene-8',1"-cyclopropane) (1c) and their denitrogenated hydrocarbon derivatives tricyclo[3.2.0.0(2,7)]heptane (2a), spiro(cyclopropane-1,3'-tricyclo[3.2.0.0(2,7)]heptane) (2b), and dispiro(cyclopropane-1,3'-tricyclo[3.2.0.0(2,7)]heptane-6'1"-cyclopropane) (2c) were investigated. It was shown that the 185-nm photochemical behavior of these substrates does not depend on the degree of spirocyclopropane substitution. As common products in the 185-nm photolysis of the azoalkanes 1a-c were obtained the tricycloalkanes 2a-c (major products), the norbornenes 3a-c, the vinylcyclopentenes 5a-c (minor products), and the exo-methylenecyclohexenes 6a-c (traces). In the case of the parent azoalkane 1a additionally bicyclo[3.2.0]hept-2-ene (4) and bicyclo[4.1.0]hept-2-ene (7a) were detected. The major products in the photolysis of the tricycloheptanes 2a-c were the vinylcyclopentenes 5a-c, but also the norbornenes 3a-c and the methylenecyclohexenes 6a-c were formed in considerable amounts. Although the norbornenes 3a-c and the bicyclo[3.2.0]heptene 4a are logical Wagner-Meerwein rearrangement products, attempts to trap the suspected radical-cationic and zwitterionic intermediates with CF3CH2OH failed. Efforts to generate the authentic radical-cationic species by means of photosensitized electron transfer (PET) by using sensitizers such as cyanoarenes, quinones, and pyrylium salts were unproductive. Vibrationally excited bicyclo[2.2.1]hepta-2,7-diyls, generated by the pyrolyses of 2a-c, are not precursors to the norbornenes 3a-c because, instead of such rearrangement products, cyclobutane cleavage of the bicyclo[2.1.0]pentane moiety takes place to afford the isomeric vinylcyclopentenes 5'a-c. Carbene intermediates, produced either from the 1,3-diyl-type species through fragmentation or from the photodenitrogenation of diazoalkanes, which are generated by retro-cleavage of n,pi* excited azoalkanes 1a-c, in turn obtained through internal conversion of higher excited states such as 1-pi,pi*, 1n,sigma*, and R(y), are proposed as the most likely precursors to either the vinylcyclopentenes 5a-c or methylenecyclohexenes 6a-c, respectively. In violation of Kasha's rule, photochemistry directly from the higher excited states of the azoalkanes 1a-c competes with internal conversion to the lowest excited state, namely the n,pi* state, as it was shown by the formation of norbornenes 3a-c.
• The protonated cyclopropane route to bicyclic cations
  作者：Wolfgang Kirmse、Joachim Streu

  DOI：10.1021/jo00380a007

  日期：1987.2
• Adam, Waldemar; Oppenlaender, Thomas, Angewandte Chemie, 1986, vol. 98, # 8, p. 659 - 670
  作者：Adam, Waldemar、Oppenlaender, Thomas

  DOI：——

  日期：——
• Bogdanovic, Borislav; Schlichte, Klaus; Westeppe, Uwe, Chemische Berichte, 1988, vol. 121, p. 27 - 32
  作者：Bogdanovic, Borislav、Schlichte, Klaus、Westeppe, Uwe

  DOI：——

  日期：——