3-methyl-3-(prop-2-enyl)cyclohexanone | 94020-17-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-methyl-3-(prop-2-enyl)cyclohexanone
• 英文别名: 3-allyl-3-methylcyclohexanone；3-Methyl-3-prop-2-enylcyclohexan-1-one
• CAS: 94020-17-4
• 化学式: C₁₀H₁₆O
• 分子量: 152.236
• InChiKey: XHCDLHACUXQKNJ-UHFFFAOYSA-N

物化性质

• 沸点：
  209.6±9.0 °C(Predicted)
• 密度：
  0.892±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  11
• 可旋转键数：
  2
• 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

反应信息

• 作为反应物：
  描述：

  3-methyl-3-(prop-2-enyl)cyclohexanone 生成 5-methyl-2-phenylselanyl-5-prop-2-enylcyclohexan-1-one
  参考文献：
  名称：

  CUNNINGHAM, I. D.;MCMURRY, T. B. H., J. CHEM. RES. SYNOP., 1984, N 7, 222

  摘要：

  DOI：
• 作为产物：
  描述：

  3-甲基-2-环己烯-1-酮 、 烯丙基三甲基硅烷 在 四氯化钛 作用下， 以 二氯甲烷 为溶剂， 反应 10.5h， 以25%的产率得到3-methyl-1,3-di(prop-2-enyl)cyclohex-1-ene
  参考文献：
  名称：

  Cunningham, Ian D.; McMurry, t. Brian H., Journal of Chemical Research, Miniprint, 1984, # 7, p. 2047 - 2059

  摘要：

  DOI：

文献信息

• Cascade Radical Carbonylations Leading to 3-Substituted Cyclohexanones
  作者：Ilhyong Ryu、Yoshitaka Uenoyama、Takahide Fukuyama

  DOI：10.1055/s-2006-949643

  日期：2006.9

  Tin radical mediated [5+1]-annulation methods leading to 3-substituted cyclohexanones were investigated. Cyclohexanones having a quaternary center at the 3-position were synthesized in good yields by allyltin-mediated three- and four-component cascade reactions that involve (i) radical carbonylation, (ii) 6-endo cyclization, and (iii) alkene addition.

  研究了锡自由基介导的 [5+1]-环化方法，导致 3-取代的环己酮。通过烯丙基锡介导的三组分和四组分级联反应，包括 (i) 自由基羰基化、(ii) 6-内环化和 (iii) 烯烃加成，以良好的产率合成了在 3 位具有四元中心的环己酮。
• A Convenient Conversion of Terminal Alkenes into Homologous Unsaturated and Doubly Unsaturated Esters
  作者：Bill Hawkins、Victoria L. Paddock、Nina Tölle、Samir Z. Zard

  DOI：10.1021/ol203387r

  日期：2012.2.17

  Unsaturated and doubly unsaturated esters have been synthesized in two steps by the application of a radical xanthate transfer process of a simple methylsulfoxide starting material to a range of terminal alkenes. syn-Elimination of the sulfoxide gives alpha,beta-unsaturated esters, which coupled with a xanthate elimination yields alpha,beta,gamma,delta-unsaturated esters.
• 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
  作者：Gary A. Molander、Jeffrey A. McKie

  DOI：10.1021/jo00013a008

  日期：1991.6

  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.
• Stereoselective Prins Cyclizations of δ,ε-Unsaturated Ketones to cis-3-Chlorocyclohexanols with TiCl4
  作者：Chad E. Davis、Robert M. Coates

  DOI：10.1002/1521-3773(20020201)41:3<491::aid-anie491>3.0.co;2-3

  日期：2002.2.1
• Cunningham, Ian D.; McMurry, t. Brian H., Journal of Chemical Research, Miniprint, 1984, # 7, p. 2047 - 2059
  作者：Cunningham, Ian D.、McMurry, t. Brian H.

  DOI：——

  日期：——