3-(3-butenyl)cyclopentanone | 22628-91-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-(3-butenyl)cyclopentanone
• 英文别名: 3--cyclopentanon；3-(3-Butenyl)cyclopentanon；3-but-3-enylcyclopentan-1-one
• CAS: 22628-91-7
• 化学式: C₉H₁₄O
• 分子量: 138.21
• InChiKey: SOVGSPFMASGWMT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  10
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-(3-butenyl)cyclopentanone 反应 24.0h， 生成 exo-Bicyclo<3.2.1>octane-2-carboxylic acid
  参考文献：
  名称：

  Facile bridged bicycloalkane synthesis via intramolecular nitrone-olefin cycloaddition

  摘要：

  DOI：

  10.1021/jo00163a052
• 作为产物：
  描述：

  (3-(but-3-enyl)cyclopent-1-enyloxy)trimethylsilane 在 盐酸 作用下， 生成 3-(3-butenyl)cyclopentanone
  参考文献：
  名称：

  A facile synthesis of bicyclo[m.n.1]alkan-1-ols. Evidence for organosamarium intermediates in the samarium(II) iodide promoted intramolecular Barbier-type reaction

  摘要：

  Samarium(II) iodide (SmI2) has been successfully employed as a reductive coupling agent for the intramolecular Barbier-type synthesis of bicyclo[m.n.1]alkan-1-ols. Thus, a variety of 3-(omega-iodoalkyl)cycloalkanones, upon treatment with SmI2 and a catalytic quantity of iron complex in tetrahydrofuran (THF), provide the title compounds in excellent yields. The reaction is quite general for the construction of diverse bicyclic ring systems, including the highly strained bicyclo[2.1.1]hexan-1-ol. In addition to exploring the synthetic utility of this reaction, studies have been performed which provide insight on the mechanistic details of the SmI2-promoted intramolecular Barbier-type synthesis. Compelling evidence for the intermediacy of organosamarium species has thus been gathered.

  DOI：

  10.1021/jo00013a008

文献信息

• Simple Construction of Bicyclo[4.3.0]nonane, Bicyclo[3.3.0]octane, and Related Benzo Derivatives by Palladium-Catalyzed Cycloalkenylation
  作者：Masahiro Toyota、Andivelu Ilangovan、Rei Okamoto、Tomohito Masaki、Makoto Arakawa、Masataka Ihara

  DOI：10.1021/ol020187u

  日期：2002.11.1

  [reaction: see text] Bicyclo[4.3.0]nonanes (hydrindanes) and bicyclo[3.3.0]octanes (octahydropentalenes) are easily synthesized by palladium-catalyzed cycloalkenylations. Additionally, benzo-fused bicyclo[3.3.0]octanes are prepared for the first time through intramolecular coupling between silyl enol ethers and aromatic rings in the presence of catalytic palladium acetate.

  [反应：见正文]双环[4.3.0]壬烷（氢化丙烷）和双环[3.3.0]辛烷（八氢戊烯）很容易通过钯催化的环烯基化反应合成。另外，在乙酸钯催化作用下，通过甲硅烷基烯醇醚与芳环之间的分子内偶联，首次制备了苯并稠合的双环[3.3.0]辛烷。
• The Synthesis of Strained Methylene-bridged Bicyclic Olefins by the IntramolecularWittig Reaction
  作者：Konrad B. Becker

  DOI：10.1002/hlca.19770600111

  日期：1977.1.26

  A convenient synthesis of the strained methylene-bridged trans-cyclooctenes bicyclo[3.3.1]-1 (2)-nonene (1), bicyclo[4.2.1]-1(8)-nonene (2), and bicyclo[4.2.1]-1(2)-nonene (3) by the intramolecular Wittig reaction is described (see Schemes 1–4). The (3-oxocycloalkyl)alkyl-phosphonium bromides 20, 27 and 38 undergoing cyclization to the bridgehead olefins are formed by simple reaction sequences. The

  应变合成的亚甲基桥连反式环辛烯双环[3.3.1] -1（2）-壬烯（1），双环[4.2.1] -1（8）-壬烯（2）和双环[4.2 [1]描述了通过分子内Wittig反应的-1（2）-壬烯（3）（参见方案1-4）。的（3-氧代环）烷基鏻溴化物20，27和38经受环化到桥头烯烃通过简单的反应顺序形成。关于烯烃的应变，讨论了其光谱特性（IR，1 H-NMR，13 C-NMR和UV）。
• Intramolecular cycloaddition reactions of exocyclic nitrones
  作者：Raymond L. Funk、Gary L. Bolton、Joy Umstead Daggett、Marvin M. Hansen、Linus H.M. Horcher

  DOI：10.1016/s0040-4020(01)96702-x

  日期：1985.1

  Exocyclic nitrones smoothly participate in intramolecular cycloaddition reactions to provide bridged and fused polycarbocycles. The exploitation of this methodology in the total syntheses of the sesquiterpenes (±)-7,12-secoishwaran-12-ol (44), (±)-hirsutene (56), (±)-coriolin (68) is also presented.

  环外硝酮平稳地参与分子内环加成反应，以提供桥连和稠合的多碳环。还介绍了该方法在倍半萜（±）-7,12-secoishwaran-12-ol（44），（±）-hirsutene（56），（±）-coriolin（68）的总合成中的应用。
• General approach to annulated 4-cyclooctenones by aliphatic Claisen rearrangement. Stereospecific total synthesis of (.+-.)-precapnelladiene
  作者：William A. Kinney、Michael J. Coghlan、Leo A. Paquette

  DOI：10.1021/ja00311a023

  日期：1985.12
• Beslin,P. et al., Bulletin de la Societe Chimique de France, 1969, # 2, p. 508 - 514
  作者：Beslin,P. et al.

  DOI：——

  日期：——