3-exo-acetyltricyclo[3.2.1.0^2,4]octane | 16529-78-5

• 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: 3-exo-acetyltricyclo[3.2.1.0^2,4]octane
• CAS: 16529-78-5
• 化学式: C₁₀H₁₄O
• 分子量: 150.221
• InChiKey: FSNJHKBVYKBMHL-NPLQXLRFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.87
• 重原子数：
  11.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  17.07
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  3-exo-acetyltricyclo[3.2.1.0^2,4]octane 、 2,4-二硝基苯肼 生成 N-(2,4-Dinitro-phenyl)-N'-[(1R,2S,3R,4R,5S)-1-tricyclo[3.2.1.0^2,4]oct-3-yl-eth-(Z)-ylidene]-hydrazine
  参考文献：
  名称：

  一种新的钌催化炔丙醇反应：降冰片烯的环丙烷化

  摘要：

  阳离子（η5-环戊二烯基）三（乙腈）钌配合物催化炔丙醇与降冰片烯在甲醇中的新反应，以定量产率得到环丙烷化产物乙酰三环辛烷。

  DOI：

  10.1246/cl.1997.1273
• 作为产物：
  描述：

  Ethanone, 1-tricyclo[3.2.1.02,4]oct-6-en-3-yl-, (1alpha,2beta,3beta,4beta,5alpha)- (9CI) 在 copper diacetate 、 一水合肼 作用下， 以 乙醇 为溶剂， 反应 24.0h， 生成 3-exo-acetyltricyclo[3.2.1.0^2,4]octane
  参考文献：
  名称：

  On an (oxatrimethylenemethane)palladium(0) complex. An unusual palladium(0)-catalyzed cyclopropanation

  摘要：

  DOI：

  10.1021/ja00194a043

文献信息

• Palladium-Catalyzed α-Ketocyclopropanation of Norbornenes with Propargyl Acetates
  作者：Yuta Tanioka、Naofumi Tsukada

  DOI：10.1021/jo500357f

  日期：2014.6.6

  reacted with norbornene in the presence of a catalytic amount of tetrakis(tripheylphosphine)palladium to give cyclopropyl ketones. The reaction proceeded with high stereoselectivity, affording a single stereoisomer. The reaction of various substituted norbornenes gave the corresponding cyclopropanes in moderate to good yields.

  乙酸炔丙酯在催化量的四（三苯甲基膦）钯存在下与降冰片烯反应，得到环丙基酮。反应以高的立体选择性进行，得到单一的立体异构体。各种取代的降冰片烯的反应以中等至良好的产率得到了相应的环丙烷。
• Ruthenium-Catalyzed Cyclopropanation of Norbornene with Propargyl Alcohol
  作者：Yuji Matsushima、Hidetoshi Kikuchi、Mitsunari Uno、Shigetoshi Takahashi

  DOI：10.1246/bcsj.72.2475

  日期：1999.11

  Norbornene as well as its 5,6-disubstituted derivatives and oxa-norbornene undergoes a novel cyclopropanation with propargyl alcohol in methanol containig cationic (η5-cyclopentadienyl)tris(acetonitrile)ruthenium complexes as catalysts to give exo-3-acetyltricyclooctane derivatives. Cyclopentadienylruthenium catalysts having an electron-withdrawing substituent on the Cp ligand exhibited the highest activity and the cyclopropanation proceeded even at −20 °C. On the basis of a deuterium labeling experiment, a reaction mechanism involving a ruthenacycle intermediate is proposed.

  降冰片烯及其 5,6-二取代衍生物和氧杂降冰片烯在甲醇中与丙炔醇发生了一种新的环丙烷化反应，该反应以阳离子 (η5- 环戊二烯基) 三（乙腈）钌络合物为催化剂，生成了外-3-乙酰基三环辛烷衍生物。在 Cp 配体上具有一个抽电子取代基的环戊二烯基钌催化剂表现出最高的活性，即使在 -20 °C 下也能进行环丙烷化反应。在氘标记实验的基础上，提出了涉及钌环中间体的反应机理。
• One-Step Synthesis of Oxodimethylenemethane−Transition Metal Complexes and Palladium-Catalyzed Cycloaddition Reaction
  作者：Isao Ikeda、Akihiro Ohsuka、Kazuyoshi Tani、Toshikazu Hirao、Hideo Kurosawa

  DOI：10.1021/jo951425k

  日期：1996.1.1

  Some alkyl allyl carbonates and an allylammonium chloride bearing (1-(butyloxy)ethyl)oxy group at the 2-position of the allyl group were synthesized and successfully transformed to oxodimethylenemethane-palladium and -platinum complexes in one step by mixing with a transition metal-(0) and triphenylphosphine. On the basis of the confirmation of vinyl ether formation by H-1 NMR, the generation of oxodimethylenemethane complexes was rationalized to occur through abstraction of the beta-hydrogen on the acetal carbon by an alkoxide ion which was generated from the allyl carbonate upon oxidative addition of the transition metal. The palladium-catalyzed cycloaddition of the acetonylidene group to strained olefins also proceeded successfully by using these alkyl allyl carbonates.
• Palladium-catalyzed reactions of ketone .alpha.-carbonates with norbornenes. An unusual cyclopropanation
  作者：Sensuke Ogoshi、Tsumoru Morimoto、Kenichi Nishio、Kouichi Ohe、Shinji Murai

  DOI：10.1021/jo00053a004

  日期：1993.1

  In the presence of a palladium(0) catalyst, ketone alpha-carbonates react with norbornene to give a cyclopropane derivative via an oxa-pi-allylpalladium intermediate.
• Synthesis and chemistry of some tricyclo[4.2.1.02,5]nonane derivatives
  作者：R. R. Sauers、S. B. Schlosberg、P. E. Pfeffer

  DOI：10.1021/jo01270a001

  日期：1968.6