2,2,6-trimethyl-4-heptyn-6-en-3-one | 132609-19-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,2,6-trimethyl-4-heptyn-6-en-3-one
• 英文别名: 2,2,6-trimethylhept-6-en-4-yn-3-one
• CAS: 132609-19-9
• 化学式: C₁₀H₁₄O
• 分子量: 150.221
• InChiKey: MZSMWMZBNUYTSI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  2,2,6-trimethyl-4-heptyn-6-en-3-one 在 8-isopropylquinoline N-oxide 、 BrettPhosAuNTf₂ 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 7.0h， 以65%的产率得到4-methacryloyl-2,2-dimethylcyclobutanone
  参考文献：
  名称：

  通过氧化金催化对环丁酮进行非重氮 CH 插入方法。

  摘要：

  环丁酮是合成用途广泛的化合物，通常需要付出大量努力才能获得。在此，我们报告了一种基于氧化生成的金卡宾的 C(sp 3 )-H 插入化学的环丁酮的简便合成。从具有最少结构预官能化的底物以合成有用的产率获得各种环丁酮。这一发现揭示了金催化炔酮氧化转化的新合成效用。

  DOI：

  10.1002/anie.202003698
• 作为产物：
  描述：

  三甲基乙酰氯 、 2-甲基-1-丁烯-3-炔 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三乙胺 作用下， 反应 24.0h， 以67%的产率得到2,2,6-trimethyl-4-heptyn-6-en-3-one
  参考文献：
  名称：

  Chemo- and Regioselective Cyclohydrocarbonylation of α-Keto Alkynes Catalyzed by a Zwitterionic Rhodium Complex and Triphenyl Phosphite

  摘要：

  alpha-Keto alkynes react with CO and H-2 in the presence of catalytic quantities of the zwitterionic rhodium complex (eta(6)-C6H5BPh3)Rh--(+)(1,5-COD) and triphenyl phosphite affording either the 2-, 2(3H)-, or 2(5H)-furanones in 61-93% yields. The cyclohydrocarbonylation is readily accomplished using substrates containing alkyl, aryl, vinyl, and alkoxy groups at the acetylenic terminal, as well as a variety of primary, secondary, and tertiary alkyl, aryl, and heteroaryl groups connected to the ketone functionality. Structural and electronic properties present in the starting materials mediate the chemo- and regioselectivity of the reaction.

  DOI：

  10.1021/jo000230w

文献信息

• Photocycloaddition of Enynones (4-Acylbut-1-en-3-ynes) to Alkenes
  作者：Inga Inhülsen、Paul Margaretha

  DOI：10.1021/ol902827s

  日期：2010.2.19

  The title compounds undergo regio- and diastereoselective [2+2]-cycloaddition at the olefinic C-C bond on irradiation (350 nm) in the presence of either methacrylonitrile or 2,3-dimethylbuta-1,3-diene, affording hitherto unknown 1-cyclobutylalk-1-yn-3-ones or 1-bicyclo[4.2.0]octylalk-1-yn-3-ones, respectively.
• Synthesis of acetylenic ketones
  作者：A. S. Zanina、S. I. Shergina、I. E. Sokolov、I. L. Kotlyarevskii

  DOI：10.1007/bf00958843

  日期：1990.11

  A general preparative method of synthesis of acetylenic ketones was developed based on acylation of terminal acetylenes with acid chlorides in the presence of Cu(I) chloride.
• A new route for the synthesis of 1,3-diketones
  作者：A. S. Zanina、S. I. Shergina、I. E. Sokolov、R. N. Myasnikova

  DOI：10.1007/bf00698504

  日期：1995.4

  A simple route for the synthesis of 1,3-diketones by the reaction of acetylenic ketones with amines followed by hydrolysis of the resulting aminovinylketons is suggested.
• Chemo- and Regioselective Cyclohydrocarbonylation of α-Keto Alkynes Catalyzed by a Zwitterionic Rhodium Complex and Triphenyl Phosphite
  作者：Bernard G. Van den Hoven、Bassam El Ali、Howard Alper

  DOI：10.1021/jo000230w

  日期：2000.6.1

  alpha-Keto alkynes react with CO and H-2 in the presence of catalytic quantities of the zwitterionic rhodium complex (eta(6)-C6H5BPh3)Rh--(+)(1,5-COD) and triphenyl phosphite affording either the 2-, 2(3H)-, or 2(5H)-furanones in 61-93% yields. The cyclohydrocarbonylation is readily accomplished using substrates containing alkyl, aryl, vinyl, and alkoxy groups at the acetylenic terminal, as well as a variety of primary, secondary, and tertiary alkyl, aryl, and heteroaryl groups connected to the ketone functionality. Structural and electronic properties present in the starting materials mediate the chemo- and regioselectivity of the reaction.
• Non‐Diazo C−H Insertion Approach to Cyclobutanones through Oxidative Gold Catalysis
  作者：Zhitong Zheng、Youliang Wang、Xu Ma、Yuxue Li、Liming Zhang

  DOI：10.1002/anie.202003698

  日期：2020.9.28

  Cyclobutanones are synthetically versatile compounds that often require extensive effort to access. Herein, we report a facile synthesis of cyclobutanones based on the C(sp3)−H insertion chemistry of oxidatively generated gold carbenes. Various cyclobutanones were obtained in synthetically useful yields from substrates with minimal structural prefunctionalization. This discovery reveals new synthetic utilities

  环丁酮是合成用途广泛的化合物，通常需要付出大量努力才能获得。在此，我们报告了一种基于氧化生成的金卡宾的 C(sp 3 )-H 插入化学的环丁酮的简便合成。从具有最少结构预官能化的底物以合成有用的产率获得各种环丁酮。这一发现揭示了金催化炔酮氧化转化的新合成效用。