hexahydro-3,5-methano-2H-cyclopentafuran | 3354-68-5

• 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: hexahydro-3,5-methano-2H-cyclopentafuran
• 英文别名: 2-oxatricyclo<4.2.1.0^4,8>nonan；3-oxatricyclo[4.2.1.0^2,5]nonane；(1R,3R,6S,7R)-4-oxatricyclo[4.2.1.03,7]nonane
• CAS: 3354-68-5
• 化学式: C₈H₁₂O
• 分子量: 124.183
• InChiKey: WKOARXCZOFTJEB-WCTZXXKLSA-N

物化性质

• 熔点：
  119-125 °C
• 沸点：
  184.6±8.0 °C(Predicted)
• 密度：
  1.101±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  9
• 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：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  6-endo-(iodomethyl)-2-norbornanone 在 sodium tetrahydroborate 作用下， 以 异丙醇 为溶剂， 反应 0.5h， 以92%的产率得到hexahydro-3,5-methano-2H-cyclopentafuran
  参考文献：
  名称：

  Photochemistry of alkyl halides. 8. Formation of a bridgehead alkene

  摘要：

  DOI：

  10.1021/ja00378a033

文献信息

• Die Synthese von 6-substituierten 2-Norbornanolen. Norbornane, 7. Mitteilung
  作者：Cyril A. Grob、Bettina Günther、Adrian Waldner

  DOI：10.1002/hlca.19810640830

  日期：1981.12.16

  The Synthesis of 6-substituted 2-Norbornanols

  6-取代的2-降冰片醇的合成
• Chemical Consequences of Long-Range Orbital Interactions in Norbornane-Based 1,4-Diol Monosulfonate Esters
  作者：Petrus M. F. M. Bastiaansen、Joannes B. P. A. Wijnberg、Aede de Groot

  DOI：10.1021/jo00118a046

  日期：1995.6

  Seven monotosylated 1,4-diols with the rigid norbornane skeleton were treated with a strong base in refluxing benzene to find out whether these compounds react by initial heterolysis of the tosylate ester bond induced by long-range orbital interactions. The tosylates 1-7 were designed to investigate the influence of the sigma-relay (U-, sickle-, or W-shaped) between the donor and acceptor end of the system, to check whether primary carbocationic ion pairs could act as intermediates, and to study conformational influences on reactivity and product formation. Tosylate 1 with a U-like arrangement of the sigma-relay reacted relatively slowly and followed reaction pathways in which no long-range orbital interactions are involved. The reaction outcome of tosylate 2 which possesses a sickle-like arrangement of the sigma-relay indicates two competitive processes with and without the involvement of long-range orbital interactions. The secondary tosylates 3, 6, and 7 which all possess a W-like arrangement reacted relatively fast and showed predominantly homofragmentation. Although an ideal W-like arrangement is present in the primary tosylates 4 and 5, no reactions in which long-range orbital interactions are involved were observed. The tosylates 6 and 7 in which the tosylate group is conformationally mobile can give rise to mixtures of products. The ratio in which these products are formed can be rationalized by using the Curtin-Hammett principle.
• Lajunen, Martti; Latva-Nirva, Esa, Journal of the Chemical Society. Perkin Transactions 2 (2001), 2000, # 4, p. 719 - 723
  作者：Lajunen, Martti、Latva-Nirva, Esa

  DOI：——

  日期：——
• Polar and anchimeric effects in the solvolysis of 6-endo-substituted 2-norbornyl-p-toluene-sulfonates
  作者：Cyril A. Grob、Bettina Gunther、Reinhard Hanreich

  DOI：10.1016/s0040-4039(01)90276-x

  日期：1981.1
• NAKAZAKI M.; NAEMURA K.; KONDO Y., J. ORG. CHEM. <JOCE-AH>, 1976, 41, NO 7, 1229-1233
  作者：NAKAZAKI M.、 NAEMURA K.、 KONDO Y.

  DOI：——

  日期：——