梯形烷
梯形烷（英文：ladderane），又称梯烷，是一种含有两个或多个稠合四元环的环烷烃。它的英文名ladderane是一个混成词，因为四元环的排列形状类似于梯子，并且是一种烷烃。有n个环的梯形烷化学式为C2n+2H2n+6。梯形烷的空间构型张力很大，因为碳原子上的配体不能使用正常的键角来成键。然而，梯形烷的例子已经在生物体内被发现。[1] 一个典型的例子是五环厌氧氨氧化酸（Pentacycloanammoxic Acid），[2] 它由五个稠合的环丁烷单元构成。它在细菌中进行厌氧氨氧化过程，这使得它形成了紧且厚的膜，这阻止了生物体失去肼中间体。后者参与了氮的产生和亚硝酸根离子与氨反应生成水。[3]
梯形烷可以由碳碳双键到单键的还原反应制得，同时伴随着新碳碳键的形成并关环。[1][4]
参考资料
- ^ 1.0 1.1 Nouri, D H, Tantillo, D J. They Came from the Deep: Syntheses, Applications, and Biology of Ladderanes. Curr. Org. Chem. 2006, 10 (16): 2055–2074. doi:10.2174/138527206778742678.
- ^ J. S. Sinninghe Damsté, M. Strous, W. I. C. Rijpstra, E. C. Hopmans, J. A. J. Geenevasen, A. C. T. van Duin, L. A. van Niftrik and M. S. M. Jetten. Linearly concatenated cyclobutane lipids form a dense bacterial membrane. Nature. 2002, 419 (6908): 708–712. PMID 12384695. doi:10.1038/nature01128.
- ^ Vincent Mascitti and E. J. Corey. Enantioselective Synthesis of Pentacycloanammoxic Acid. J. Am. Chem. Soc. 2006, 128 (10): 3118. PMID 16522072. doi:10.1021/ja058370g.
- ^ Nouri, D H and Tantillo, D J. Ladderane Formation Mechanisms: The Uphill Battle. 232nd ACS National Meeting, San Francisco, CA, September 10-14, 2006: COMP 247.
- Henning Hopf. "Chains, rings, substituents: Tales from the marvelous edifice of modern organic chemistry." Lecture at the 234th American Chemical Society National Meeting in Boston, MA on Tuesday, August 21, 2007, 2:45 to 3:30 PM.
- Ladderane lipids website, UC Davis （页面存档备份，存于互联网档案馆）