2-but-3-ynyl-3-methylcyclohex-2-enone | 87020-29-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-but-3-ynyl-3-methylcyclohex-2-enone
• 英文别名: 2-But-3-ynyl-3-methylcyclohex-2-en-1-one
• CAS: 87020-29-9
• 化学式: C₁₁H₁₄O
• 分子量: 162.232
• InChiKey: IIEGGDQEAFUGGU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.55
• 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-but-3-ynyl-3-methylcyclohex-2-enone 在 alkaline hydrogen peroxide 作用下， 生成 1-but-3-yn-1-yl-6-methyl-7-oxabicyclo[4.1.0]heptan-2-one
  参考文献：
  名称：

  3-甲基环己-2-烯酮衍生物作为环化反应的引发剂。第1部分。2-取代的3-甲基环己-2-烯酮的引入和合成

  摘要：

  使用哈格曼酯途径已经制备了一系列的C-2取代的3-甲基环己-2-烯酮。已经开发了这些化合物的新合成方法，其涉及1-羟基-5-甲基环己-1,5-二烯的N，N-二乙基氨基乙基醚的烷基化。使用碱性过氧化氢已将环己酮转化为相应的α，β-环氧酮。

  DOI：

  10.1039/p19830000747
• 作为产物：
  描述：

  在 水 作用下， 以 乙腈 为溶剂， 以403 mg的产率得到2-but-3-ynyl-3-methylcyclohex-2-enone
  参考文献：
  名称：

  An efficient one-pot four-step domino reaction for the synthesis of C2-substituted 3-methylcyclohex-2-enones

  摘要：

  An efficient one-pot four-step domino reaction of substituted beta-ketoesters has been optimized giving rise to a large panel of C2-substituted 3-methylcyclohex-2-enones, an important scaffold for the preparation of various initiators for cationic or radical cyclizations. The developed methodology is quite general and applicable to a wide range of beta-ketoester substrates, allowing the introduction of various functionalities at the C2 position of the 3-methylcyclohex-2-enones, in good to excellent yields. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.07.029

文献信息

• 3-Methylcyclohex-2-enone derivatives as initiators of cyclisation. Part 1. Introduction and synthesis of 2-substituted 3-methylcyclohex-2-enones
  作者：Joseph A. Amupitan、Enamul Huq、Michael Mellor、Edward G. Scovell、James K. Sutherland

  DOI：10.1039/p19830000747

  日期：——

  A series of C-2 substituted 3-methylcyclohex-2-enones has been prepared using the Hagemann ester route. A new synthesis of these compounds has been developed which involves the alkylation of the N,N-diethylaminoethyl ether of 1-hydroxy-5-methylcyclohexa-1,5-diene. The cyclohexenones have been converted into the corresponding α,β-epoxyketones using alkaline hydrogen peroxide.

  使用哈格曼酯途径已经制备了一系列的C-2取代的3-甲基环己-2-烯酮。已经开发了这些化合物的新合成方法，其涉及1-羟基-5-甲基环己-1,5-二烯的N，N-二乙基氨基乙基醚的烷基化。使用碱性过氧化氢已将环己酮转化为相应的α，β-环氧酮。
• AMUPITAN, J. A.;HUQ, E.;MELLOR, M.;SCOVELL, E. G.;SUTHERLAND, J. K., J. CHEM. SOC. PERKIN TRANS., 1983, N 4, 747-749
  作者：AMUPITAN, J. A.、HUQ, E.、MELLOR, M.、SCOVELL, E. G.、SUTHERLAND, J. K.

  DOI：——

  日期：——
• An efficient one-pot four-step domino reaction for the synthesis of C2-substituted 3-methylcyclohex-2-enones
  作者：Sylvie Goncalves、Philippe Maillos、Marc Nicolas、Alain Wagner、Rachid Baati

  DOI：10.1016/j.tet.2010.07.029

  日期：2010.9

  An efficient one-pot four-step domino reaction of substituted beta-ketoesters has been optimized giving rise to a large panel of C2-substituted 3-methylcyclohex-2-enones, an important scaffold for the preparation of various initiators for cationic or radical cyclizations. The developed methodology is quite general and applicable to a wide range of beta-ketoester substrates, allowing the introduction of various functionalities at the C2 position of the 3-methylcyclohex-2-enones, in good to excellent yields. (C) 2010 Elsevier Ltd. All rights reserved.
• Cationic cyclization of keto-epoxides mediated by zirconium(IV) tetrachloride: diastereoselective synthesis of cis-decalinols
  作者：Sylvie Goncalves、Marc Nicolas、Philippe Maillos、Rachid Baati

  DOI：10.1016/j.tet.2011.08.050

  日期：2011.10

  10-Methyl-cis-9-decalinols are important motifs in several natural products and key intermediates in total synthesis. Herein, we wish to describe a highly chemo- and diastereoselective cyclization of ketoepoxides leading to 10-methyl-cis-9-decalinols. This method based on the use of zirconium(IV) tetrachloride permits the access to a wide variety of cis-decalinols in good to excellent yields. The cationic cyclization could also be performed with chiral keto-epoxide with complete control of the diastereoselectivity affording cis-bicyclic tertiary alcohol with good enantiomeric excess. The chemo- and the diastereoselectivity are assumed to result from the ability of Zr(IV) to generate highly stable bidentic complexes with alpha-hydroxy-ketone intermediates. (C) 2011 Elsevier Ltd. All rights reserved.