3-丁-3-烯基环己烷-1-酮 | 3636-03-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 3-丁-3-烯基环己烷-1-酮
• 英文名称: 3-(3-butenyl)cyclohexan-1-one
• 英文别名: 3-(3'-butenyl)cyclohexanone；3-(but-3-enyl)cyclohexanone；1--cyclohexanon-(3)；3-(Buten-(3)-yl)-cyclohexanon；3-(3-Butenyl)cyclohexanone；3-but-3-enylcyclohexan-1-one
• CAS: 3636-03-1
• 化学式: C₁₀H₁₆O
• 分子量: 152.236
• InChiKey: RPHSBKFTOZOTRQ-UHFFFAOYSA-N

物化性质

• 沸点：
  222.9±9.0 °C(Predicted)
• 密度：
  0.902±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 海关编码：
  2914299000

反应信息

• 作为反应物：
  描述：

  3-丁-3-烯基环己烷-1-酮 在 三氟化硼乙醚 氧气 、 copper(l) chloride 、 palladium dichloride 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.5h， 生成 2-hydroxyethyl 4-(3-methylcyclopent-2-en-1-yl)butanoate
  参考文献：
  名称：

  Ring cleavage and reconstruction of five and six membered ring

  摘要：

  DOI：

  10.1016/s0040-4039(00)95516-3
• 作为产物：
  描述：

  2-环己烯-1-酮 在 盐酸 、 四甲基乙二胺 作用下， 生成 3-丁-3-烯基环己烷-1-酮
  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

• Perhydrolysis in Ethereal H₂O₂ Mediated by MoO₂(acac)₂: Distinct Chemoselectivity between Ketones, Ketals, and Epoxides
  作者：Xiaosheng An、Qinghong Zha、Yikang Wu

  DOI：10.1021/acs.orglett.9b00425

  日期：2019.3.1

  Ketones, ketals, and epoxides were converted into corresponding hydroperoxides in high yields by reaction with ethereal H2O2 in the presence of a catalytic amount of MoO2(acac)2 with distinct (to date unattainable) chemoselectivity.

  在催化量的MoO 2（acac）2具有催化选择性（迄今为止无法实现）的条件下，通过与醚H 2 O 2反应，高产率地将酮，缩酮和环氧化物转化为相应的氢过氧化物。
• 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。
• An efficient and versatile method for the preparation of α-keto acid derivatives from terminal alkenes
  作者：Yung-Son Hon、Wei-Chih Lin

  DOI：10.1016/0040-4039(95)01638-x

  日期：1995.10

  Ozonolysis of terminal alkenes followed by reacting with a preheated mixture of CH2Br2-Et2NH affords α-substituted acroleins, which can be converted to α-keto acid derivatives in three steps, under very mild reaction conditions.

  末端烯烃的臭氧分解，然后与CH 2 Br 2 -Et 2 NH的预热混合物反应，得到α-取代的丙烯醛，可以在非常温和的反应条件下分三步将其转化为α-酮酸衍生物。
• 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。
• Gold‐ vs. Platinum‐Catalyzed Polycyclizations by <i>O</i> ‐Acyl Migration. Solvent‐Free Reactions
  作者：Xavier Moreau、Jean‐Philippe Goddard、Matthieu Bernard、Gilles Lemière、Juan Manuel López‐Romero、Emily Mainetti、Nicolas Marion、Virginie Mouriès、Serge Thorimbert、Louis Fensterbank、Max Malacria

  DOI：10.1002/adsc.200700356

  日期：2008.1.4

  Polycyclic derivatives incorporating a cyclopropyl group have been efficiently synthesized from propargyl acetates using platinum(II), gold(I) and gold(III) catalysis. These reactions which are also viable for the preparation of medium-sized rings, proceed with a complete diastereocontrol and can also be run in neat conditions.

  使用铂（II），金（I）和金（III）催化，可从乙酸炔丙酯高效合成具有环丙基的多环衍生物。这些反应对于制备中型环也是可行的，可以进行完全的非对映控制，也可以在纯净条件下进行。