exo-(2-methyl)norbornane | 872-78-6

• 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: exo-(2-methyl)norbornane
• 英文别名: (+/-)-2exo-methyl-norbornane；(+/-)-2exo-Methyl-norbornan；(1R,2R,4R)-2-methylbicyclo[2.2.1]heptane
• CAS: 872-78-6
• 化学式: C₈H₁₄
• 分子量: 110.199
• InChiKey: KWSARSUDWPZTFF-BWZBUEFSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  8
• 可旋转键数：
  0
• 环数：
  2.0
• 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：

  三氯化铝 、 exo-(2-methyl)norbornane 、 (+/-)-2endo-methyl-norbornane 生成 双环[3.2.1]辛烷 、 4-甲基二环[2.2.1]庚烷 、 八氢-并环戊二烯
  参考文献：
  名称：

  Turowa-Poljak et al., Zhurnal Obshchei Khimii, 1959, vol. 29, p. 1078

  摘要：

  DOI：
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 lithium aluminium tetrahydride 、 二乙二醇二甲醚 作用下， 生成 exo-(2-methyl)norbornane
  参考文献：
  名称：

  5-Norbornenyl- and 2-norbornylcarbene intermediates

  摘要：

  DOI：

  10.1021/jo00810a026

文献信息

• Stereoselectivity of ring closure of substituted hex-5-enyl radicals
  作者：Athelstan L. J. Beckwith、Tony Lawrence、Algirdas K. Serelis

  DOI：10.1039/c39800000484

  日期：——

  1,5-Ring closure of 1- or 3-substituted hex-5-enyl radicals affords mainly cis-disubstituted cyclic products, whereas 2- or 4-substituted species give mainly trans-products; the significance of this stereoselectivity is demonstrated in the formation of the norbornane system from acyclic precursors.

  1-或3-取代的六-5-烯基的1，5-环闭合主要提供顺式-二取代的环状产物，而2-或4-取代的物质主要提供反式产物。这种立体选择性的重要性在由无环前体形成降冰片烷体系中得到了证明。
• Highly stereoselective tandem cyclizations of 5-hexenyllithiums: preparation of endo-2-substituted bicyclo[2.2.1]heptanes and 3-substituted trans-bicyclo[3.3.0]octanes
  作者：William F. Bailey、Atmaram D. Khanolkar、Kaustubh V. Gavaskar

  DOI：10.1021/ja00047a013

  日期：1992.10

  diolefinic alkyl iodides by low-temperature lithium-iodine exchange, proceeds via two highly stereoselective and totally regiospecific 5-exo-trig ring closures to deliver bicyclic alkyllithiums. Trapping of the organolithium product by addition of an electrophile cleanly affords functionalized bicyclic molecules in good yield. In this way both endo-2-substituted bicyclo[2.2.1]heptanes and 3-substituted

  通过低温锂碘交换衍生自无环二烯烷基碘的二烯烷基锂的串联环化，通过两个高度立体选择性和完全区域特异性的 5-exo-trig 闭环进行，以提供双环烷基锂。通过添加亲电子试剂捕获有机锂产物，可以以良好的收率干净地提供功能化的双环分子。以这种方式，内-2-取代的双环[2.2.1]庚烷和3-取代的反-双环[3.3.0]辛烷均以65-80%的分离产率从容易获得的3-(2-碘乙基) )-1,5-己二烯 (5) 和 7-iodo-4-ethenyl-1-heptene (9)，分别
• Substituent effects on1H chemical shifts. I—complete1H chemical shift assignments of methyl-substituted cyclic systems
  作者：Julie Fisher、Michael J. Gradwell

  DOI：10.1002/mrc.1260300412

  日期：1992.4

  1H chemical shift assignments are presented for 2‐methyladamantane, 2‐methylnorbornane (endo and exo) and 2‐methylnorbornene (endo and exo). Resonance assignment was achieved using a variety of 1D and 2D homo‐ and heteronuclear (1H–13C) experiments. The methyl group‐induced substituent chemical shift (SCS) is derived and the SCS of protons vicinal to this group is discussed.

  给出了 2-甲基金刚烷、2-甲基降冰片烷（内型和外型）和 2-甲基降冰片烯（内型和外型）的 1H 化学位移分配。使用各种 1D 和 2D 同核和异核 (1H-13C) 实验实现了共振分配。导出了甲基诱导的取代基化学位移 (SCS)，并讨论了该基团附近质子的 SCS。
• Carbon-13 NMR and IR Spectroscopic Studies on Some 7-Oxabicyclo[2.2.1]heptanes and -heptenes. n–π Interaction and Hydrogen Bonding
  作者：Yasuhisa Senda、Akihiko Ohno、Jun-ichi Ishiyama、Shin Imaizumi、Shin-ichi Kamiyama

  DOI：10.1246/bcsj.60.613

  日期：1987.2

  diastereomeric pairs of the title compounds together with some tetrahydrofurans were examined and the chemical shifts were compared with those for the corresponding bicyclo[2.2.1]heptanes and -heptenes. The intramolecular interaction between the n-orbital of an oxygen atom and the π-orbital of an olefinic bond was found in 2-methylene-7-oxabicyclo[2.2.1]heptane. Intramolecular hydrogen bonding between the 7-oxygen

  检查了标题化合物与一些四氢呋喃的非对映体对的 13C NMR 光谱，并将化学位移与相应双环 [2.2.1] 庚烷和庚烯的化学位移进行了比较。在 2-亚甲基-7-氧杂双环 [2.2.1] 庚烷中发现了氧原子的 n-轨道和烯键的 π-轨道之间的分子内相互作用。7-氧和羟基之间的分子内氢键发生在外-7-氧杂双环[2.2.1]庚烷-2-甲醇中。
• New Functionalized Vinyl Monomers by Ethylene-(Functionalized)-Norbornene Hetero-Trimerization Catalyzed by Cobalt(II)-(Imino)pyridine Complexes
  作者：Alessandro Toti、Giuliano Giambastiani、Claudio Bianchini、Andrea Meli、Lapo Luconi

  DOI：10.1002/adsc.200800201

  日期：2008.8.4

  On activation by MAO the (imino)pyridine cobalt(II) complex CoCl2N2 catalyzes the enchainment of one norbornene (NB) molecule with two ethylene molecules to give exo-2,exo-3-ethylvinylnorbornane with high activity and complete diastereoselectivity. Turnover frequencies [TOF, mol NB (mol Co×h)−1] as high as 270,000 have been obtained. The 2E-1NB hetero-trimerization reaction has been also accomplished

  在通过MAO活化后，（亚氨基）吡啶钴（II）配合物CoCl 2 N 2催化一个降冰片烯（NB）分子与两个乙烯分子的链结，从而得到具有高活性和完全非对映选择性的外型-2，外型-3-乙基乙烯基降冰片烷。已获得高达270,000的周转频率[TOF，mol NB（mol Co×h）-1 ]。带有极性取代基（如降冰片烯甲醇和降冰片烯羧酸）的NB还可完成2E-1NB异三聚反应，条件是底物受三异丁基铝和对空间要求较低的复杂CoCl 2 N 2的保护。用作催化剂前体。在实验证据的基础上，提出了一种异三聚反应的机理。