endo-tricyclo{3.2.10(2,4)}octane | 22389-16-8

• 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: endo-tricyclo{3.2.10(2,4)}octane
• 英文别名: endo-tricyclo[3.2.1.0^2,4]octane；(1R,2R,4S,5S)-tricyclo[3.2.1.02,4]octane
• CAS: 22389-16-8
• 化学式: C₈H₁₂
• 分子量: 108.183
• InChiKey: PSZPCAFRANQPLS-KVFPUHGPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  8
• 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

安全信息

• 海关编码：
  2902199090

反应信息

• 作为反应物：
  描述：

  endo-tricyclo{3.2.10(2,4)}octane 在 次氯酸叔丁酯 作用下， 以 四氯化碳 为溶剂， 生成 anti-8-Chlor-endo-tricyclo<3,2,1,0^2,4>octan
  参考文献：
  名称：

  Radical chlorination of exo- and endo-tricyclo[3.2.1.02,4]octane and exo,exo- and exo,endo-tetracyclo[3.3.1.02,4.06,8]nonane with tert-butyl hypochlorite

  摘要：

  DOI：

  10.1021/ja00840a046
• 作为产物：
  描述：

  endo-tricyclo<3.2.1.0^2,4>oct-6-ene 在 platinum(IV) oxide 氢气 作用下， 以 四氢呋喃 为溶剂， 生成 endo-tricyclo{3.2.10(2,4)}octane
  参考文献：
  名称：

  某些三环[3.2.1.0 2,4 ]辛烷衍生物的制备和结构

  摘要：

  1,2,3,4-四氯-5,5- <异甲氧基环戊-1,3-二烯与环丙烯的Diels-Alder反应已用于提供某些内-三环[3.2.1.0 2,4 ]辛烷衍生物。几个exo -tricyclo [3.2.1。使用标准反应从已知的前体合成2,4 ]辛烷衍生物。讨论了（最终）乙酸7-降冰片二烯基乙酸酯与重氮甲烷反应生成的四环醇的立体化学。提出并讨论了许多三环[3.2.1.0 2,4 ]辛烷衍生物的PMR谱图。

  DOI：

  10.1016/s0040-4020(01)82700-9

文献信息

• Facile Activation of Zinc. Preparation of Cyclobutanones via Dichloroketene and Cyclopropanes Using the Simmons-Smith Reaction
  作者：Yngve Stenstr⊘m

  DOI：10.1080/00397919208021545

  日期：1992.11

  Abstract Zinc powder activated by heating in an inert atmosphere gave good yields when used for the title reactions. The very easy work up procedure for the cyclobutanones further increases the potential of the method.

  摘要 在惰性气氛中加热活化的锌粉在用于标题反应时具有良好的产率。环丁酮的非常简单的后处理程序进一步增加了该方法的潜力。
• Reactivity of<i>exo</i>- and<i>endo</i>-Tricyclo[3.2.1.0^2,4]octan-8-ylidenes and 7-Norbornenylidene
  作者：Shun-ichi Murahashi、Kazuo Okumura、Yusuke Maeda、Akio Sonoda、Ichiro Moritani

  DOI：10.1246/bcsj.47.2420

  日期：1974.10

  endo-Tricyclo[3.2.1.02,4]octan-8-ylidene (2) generated by the thermolysis of sodium salt of endo-tricyclo[3.2.1.02,4]octan-8-one tosylhydrazone (5) gave toluene (3.9%), cyclohepta-1,4-diene(6, 14%), cyclohepta-1,3-diene(7, 3.5%), bicyclo[3.3.0]octa-1,6-diene(8, 4.8%), bicyclo[3.3.0]octa-1,7-diene(9, 9.0%), and endo-tricyclo[3.2.1.02,4]octane (10, 21%). In sharp contrast, exo-tricyclo[3.2.1.02,4]oct-8-ylidene

  由内三环[3.2.1.02,4]辛烷-8-酮甲苯磺酰腙(5)的钠盐热解生成的内-三环[3.2.1.02,4]辛-8-亚基(2)得到甲苯(3.9%) ), cyclohepta-1,4-diene(6, 14%), cyclohepta-1,3-diene(7, 3.5%), bicyclo[3.3.0]octa-1,6-diene(8, 4.8%),双环[3.3.0]辛烷-1,7-二烯(9, 9.0%)和内三环[3.2.1.02,4]辛烷(10, 21%)。与此形成鲜明对比的是，外型三环 [3.2.1.02,4] oct-8-ylidene (1) 得到甲苯 (1.5%) 和三环 [5.1.01,7]oct-5-ene (14, 57%)。结果表明二价碳的 p 轨道与环丙烷的对称沃尔什轨道之间存在显着的同共轭相互作用。这与 7-降冰片亚基 (3) 的结果一致，其中二价碳和碳碳双键之间的相互作用稳定了非经典亚甲基。
• Interaction of diazoalkanes with unsaturated compounds
  作者：U. M. Dzhemilev、V. A. Dokichev、I. O. Maidanova、O. M. Nefedov、Yu. V. Tomilov

  DOI：10.1007/bf00704005

  日期：1993.4

  nature of the transition metal and does not depend on its valent state or ligand environment. The reaction proceeds predominantly asexo-cycloaddition of the methylene fragment. The greatest amount ofendo-isomer (up to 47 %) is formed in cyclopropanation of norbornadiene andexo-tricyclo[3.2.1.02,4]oct-6-ene in the presence of Cu and Rh compounds.

  已经研究了在 Cu、Pd 和 Rh 化合物存在下降冰片烯与重氮甲烷的环丙烷化的立体化学。环丙烷化的立体选择性取决于过渡金属的性质，而不取决于其价态或配体环境。该反应主要进行亚甲基片段的无外环加成。在 Cu 和 Rh 化合物的存在下，降冰片二烯和外型三环 [3.2.1.02,4] oct-6- 烯的环丙烷化反应会形成最大量的内异构体（高达 47%）。
• Reaction of diazoalkanes with unsaturated compounds Communication 1. Cyclopropanation of olefins with diazomethane in the presence of copper compounds
  作者：O. M. Nefodov、I. E. Dolgii、Yu. V. Tomilov、V. G. Bordakov

  DOI：10.1007/bf00956238

  日期：1984.1
• Stereodirecting effect of a substrate methoxy substituent on the addition of singlet methylene to a double bond
  作者：Terry A. Young、Colleen O'Rourke、Nathan B. Gray、Brian D. Lewis、Curt A. Dvorak、Kan Shuh Kuen、JoAnn P. DeLuca

  DOI：10.1021/jo00075a016

  日期：1993.11

  The stereodirecting effects of substrate methoxy, hydroxy, methylthio, and methyl substituents were examined in the addition of 1:CH2 to the double bonds of substrates 1a-d. The carbene, generated by photolysis of CH2N2, inserted into the C-H bonds of solvent and substrate, added to the substrate double bond to give products 2a-d, and attacked the oxygen or sulfur atom of substrates 1a-c to produce ylide intermediates which underwent 2,3-sigmatropic rearrangement to give products 3a-c. A preference for addition syn to the methoxy group of substrate 1a was observed when the reaction was run in pentane solution (syn-2a/anti-2a, 1.14 +/- 0.02), while a preference for formation of anti-2a was observed in diethyl ether solution (syn-2a/anti-2a, 0.92 +/- 0.03). A preference for 1:CH2 addition anti to the substrate substituent was observed for substrates 1b-d in both pentane and ether solution. The effect of the methoxy substituent was also examined in the addition of 1:CH2 to syn-7-methoxynorbornene (5b). Explanations for the substituent effects are offered based on both steric hindrance and interaction between 1:CH2 and the substituent, including formation and subsequent reaction of the ylide intermediates.