十四碳-13-烯-2-酮 | 33965-97-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 十四碳-13-烯-2-酮
• 英文名称: tetradec-13-en-2-one
• CAS: 33965-97-8
• 化学式: C₁₄H₂₆O
• 分子量: 210.36
• InChiKey: JVMKBOUWFQEDMF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  15
• 可旋转键数：
  11
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.79
• 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：

  十四碳-13-烯-2-酮 在 氧气 、 臭氧 、 溶剂黄146 、 三乙酰氧基硼氢化钠 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以98%的产率得到13-羟基-2-十三酮
  参考文献：
  名称：

  摘要：

  13-Hvdroxy-2-oxotridecane, which is isolated from extract of Evodia hupehensis Dode honey-bee eggs and actively attracts honey bees, is synthesized via ozonolysis of 1-methylcyclododecene and tetradec-13-en-2-one, the product from monoalkylation of the acetoacetic ester with 1-bromo-10-undecene followed by decarbethoxylation, with further reduction of the intermediate peroxides using NaBH(OAc)(3).

  DOI：

  10.1023/a:1012351524532
• 作为产物：
  描述：

  11-溴-1-十一烯 在 乙醇 、 sodium 、 lithium iodide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 30.0h， 生成 十四碳-13-烯-2-酮
  参考文献：
  名称：

  摘要：

  13-Hvdroxy-2-oxotridecane, which is isolated from extract of Evodia hupehensis Dode honey-bee eggs and actively attracts honey bees, is synthesized via ozonolysis of 1-methylcyclododecene and tetradec-13-en-2-one, the product from monoalkylation of the acetoacetic ester with 1-bromo-10-undecene followed by decarbethoxylation, with further reduction of the intermediate peroxides using NaBH(OAc)(3).

  DOI：

  10.1023/a:1012351524532

文献信息

• Mass Spectrometry and Organic Analysis, part 14. The photolysis and mass spectra of medium and large ring ketones from C9 to C16
  作者：K. H. Schulte-Elte、B. Willhalm、A. F. Thomas、M. Stoll、G. Ohloff

  DOI：10.1002/hlca.19710540703

  日期：1971.11.1

  cyclic ketones from C9 to C16 has been carried out, and formation of cyclobutanols observed in only C11 to C16. Although in the mass spectrometer cyclobutanols are not formed, an initial transfer of a γ-hydrogen atom to the carbonyl group is shown to occur in the mass spectra of all cyclic ketones higher than C10.

  已经进行了环酮从C 9到C 16的光解，仅在C 11到C 16中观察到了环丁醇的形成。尽管在质谱仪中未形成环丁醇，但在所有高于C 10的环状酮的质谱图中均显示出γ-氢原子向羰基的初始转移。
• Acylation of Unsaturated Halides, Alcohols, Esters and Ketones
  作者：Didier Barbry、Catherine Faven、Aziz Ajana

  DOI：10.1080/00397919308013794

  日期：1993.11

  Abstract treatment of the title compounds with acyl halide and Lewis acid affords unsaturated ketones (mainly α-β with aluminium chloride, selectively β-γ with silver tetrafluoroborate). Reduction of the alkenyl group gives polyfunctional ketones.

  摘要用酰卤和路易斯酸处理标题化合物得到不饱和酮（主要是α-β与氯化铝，选择性β-γ与四氟硼酸银）。烯基的还原得到多官能酮。
• Reactivity and properties of bis(chlorodifluoroacetyl) peroxide generated <i>in situ</i> from chlorodifluoroacetic anhydride for chlorodifluoromethylation reactions
  作者：Shintaro Kawamura、Cassandra J. Henderson、Yuma Aoki、Daisuke Sekine、Shū Kobayashi、Mikiko Sodeoka

  DOI：10.1039/c8cc05905e

  日期：——

  We developed a practical chlorodifluoromethylation reaction mediated by diacyl peroxide generated in situ from chlorodifluoroacetic anhydride. Allylic and amino-chlorodifluoromethylations of alkenes proceeded well with the combination of this reagent, Cu(II) catalyst and a pyridine additive. Carbo- and aromatic chlorodifluoromethylations proceeded under metal-free conditions.

  我们开发了一种实用的氯二氟甲基化反应，该反应由氯二氟乙酸酐原位生成的二酰基过氧化物介导。该试剂，Cu（II）催化剂和吡啶添加剂的组合，烯烃的烯丙基和氨基-氯二氟甲基化反应进展顺利。碳和芳香族氯二氟甲基化反应在无金属条件下进行。
• Chemoselectivity in the chromium(II)-mediated synthesis of E-alkenylstannanes from aldehydes and Bu3SnCHBr2
  作者：David M. Hodgson、Lee T. Boulton、Graham N. Maw

  DOI：10.1016/s0040-4039(00)76805-5

  日期：1994.4

  The synthesis of functionalised E-alkenylstannanes from aldehydes and a mixture of Bu3SnCHBr2, LiI and CrCl2 is described.

  描述了由醛和Bu 3 SnCHBr 2，LiI和CrCl 2的混合物合成官能化的E-链烯基锡烷。
• Scope of the chromium(II)-mediated synthesis of E-alkenylstannanes from aldehydes and Bu3SnCHBr2
  作者：David M Hodgson、Lee T Boulton、Graham N Maw

  DOI：10.1016/0040-4020(95)00086-n

  日期：1995.3

  The synthesis of E-alkenylstannanes from aldehydes and a mixture of Bu3SnCHBr2, LiI and CrCl2 is described. A mechanism is proposed to account for the alkene geometry in chromium(II)-mediated alkene synthesis which involves stereoselective addition by a gem-dichromium reagent to an aldehyde followed by a stereospecific elimination step.

  描述了由醛和Bu 3 SnCHBr 2，LiI和CrCl 2的混合物合成E-烯基锡烷。提出了一种机制来解释在铬（II）介导的烯烃合成中的烯烃几何结构，该机理包括通过宝石-二铬试剂向醛立体选择性加成到醛中，然后进行立体有择的消除步骤。