tert-butyl-isopropyl-ketene | 71106-63-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: tert-butyl-isopropyl-ketene
• 英文别名: 2-isopropyl-3,3-dimethyl-but-1-en-1-one
• CAS: 71106-63-3
• 化学式: C₉H₁₆O
• 分子量: 140.225
• InChiKey: ZRXUORVEFHEVDG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.78
• 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：

  tert-butyl-isopropyl-ketene 、 正丁胺 以 乙腈 为溶剂， 生成 N-butyl-2-isopropyl-3,3-dimethyl-butyramide
  参考文献：
  名称：

  Ketenes的胺化：动力学和机理研究。

  摘要：

  与之形成鲜明对比的是，PhMe（2）SiCH = C = O（6）与胺在CH（3）CN中形成酰胺反应的速率常数最适合与[胺]混合的二阶和三阶依赖性以前对Ph（2）C = C = O和其他反应性烯酮的研究，其中在H（2）O或CH（3）CN中仅观察到对[胺]的一级依赖。派生的6的三阶速率常数取决于胺的碱性，与CF（3）CH（2）NH（2）相比，n-BuNH（2）具有1.7 x 10（7）更大的反应性。这些动力学结果与最近报道的CH（2）= C = O与NH（3）反应的理论研究相一致。对于6，在CH（3）CN中的相对反应性k（n-BuNH（2））/ k（H（2）O）估计为10（13）。拥挤的乙烯酮t-Bu（2）C = C = O（10）极易失活并发生胺化反应，在纯正n-BuNH（2）中的反应速率比10-12慢10（12）和2 x 10（5）倍。 t-BuCH = C = O和t-BuC（i-Pr）=

  DOI：

  10.1021/jo982054l
• 作为产物：
  描述：

  2-isopropyl-3,3-dimethyl-butyryl chloride 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 生成 tert-butyl-isopropyl-ketene
  参考文献：
  名称：

  Allen, Annette D.; Baigrie, Lynn M.; Gong, Leyi, Canadian Journal of Chemistry, 1991, vol. 69, # 1, p. 138 - 145

  摘要：

  DOI：

文献信息

• Gas-phase thermolyses. Part 3. Gas-phase thermolysis of silylated thionocarboxylic acid derivatives: a route to thioketens?
  作者：Lars Carlsen、Helge Egsgaard、Ernst Schaumann、Herbert Mrotzek、Wolf-R�diger Klein

  DOI：10.1039/p29800001557

  日期：——

  The unimolecular gas-phase thermolytic decomposition of three silylated thionocarboxylic acid derivatives (2b), (3), and (8) have been studied by the flash vacuum thermolysis–field ionization mass spectrometry technique in the temperature range from 783 to 1 404 K in order to elucidate its possible applicability as a route to thioketens. Only very minor amounts of the expected thioketens were found

  通过闪蒸真空热解-场电离质谱技术在783至1404 K为了阐明其可能的用途，作为通往硫酮的途径。仅发现了极少量的预期硫酮，而相应的酮却是主要产物。讨论了keten形成的可能机制。
• Competing reaction pathways in the cycloaddition of 3-(dimethylamino)-2H-azirines with ketenes
  作者：Ernst Schaumann、Susanne Grabley、Michel Henriet、Leon Ghosez、Roland Touillaux、Jean Paul Declercq、Gabriel Germain、Maurice Van Meerssche

  DOI：10.1021/jo01303a006

  日期：1980.7
• First Examples of Reactions of AzoleN-Oxides with Thioketones: A Novel Type of Sulfur-Transfer Reaction
  作者：Grzegorz Mlostoń、Tomasz Gendek、Heinz Heimgartner

  DOI：10.1002/(sici)1522-2675(19980909)81:9<1585::aid-hlca1585>3.0.co;2-n

  日期：1998.9.9

  The reactions of 1,4,5-trisubstituted imidazole 3-oxides 1a-k with cyclobutanethiones 5a,b in CHCl3 at room temperature give imidazole-2(3H)-thiones 9a-k in high yield. The second product formed in this reaction is 2,2,4,4-tetramethylcyclobutane-1,3-dione (6a; Scheme 2). Similar reactions occur with 1 and adamantanethione (5c) as thiocarbonyl compound, as well as with 1,2,4-triazole-4-oxide derivative 10 and 5a (Scheme 3). A reaction mechanism by a two-step formation of the formal cycloadduct of type 7 via zwitterion 16 is proposed in Scheme 5. Spontaneous decomposition of 7 yields the products of this novel sulfur-transfer reaction. The starting imidazole 3-oxides are conveniently prepared by heating a mixture of 1,3,5-trisubstituted hexahydro-1,3,5-triazines 3 and alpha-(hydroxyimino) ketones 2 in EtOH (cf: Scheme 1). As demonstrated in the case of 9d, a 'one-pot' procedure allows the preparation of 9 without isolation of the imidazole 3-oxides 1. The reaction of Ic with thioketene 12 leads to a mixture of four products (Scheme 4). The minor products, 9c and the ketene 15, result from an analogous sulfur-transfer reaction (Path a in Scheme 5), whereas the parent imidazole 14 and thiiranone 13 are the products of an oxygen-transfer reaction (Path b in Scheme 5).
• Schaumann,E.; Ehlers,J., Chemische Berichte, 1979, vol. 112, p. 1000 - 1011
  作者：Schaumann,E.、Ehlers,J.

  DOI：——

  日期：——
• ALLEN, ANNETTE D.;BAIGRIE, LYNN M.;GONG, LEYI;TIDWELL, THOMAS T., CAN. J. CHEM., 69,(1991) N, C. 138-145
  作者：ALLEN, ANNETTE D.、BAIGRIE, LYNN M.、GONG, LEYI、TIDWELL, THOMAS T.

  DOI：——

  日期：——