3-cyclohexylbut-3-en-2-one | 34970-11-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-cyclohexylbut-3-en-2-one
• 英文别名: 2-Cyclohexylbut-1-en-3-on；3-Cyclohexyl-3-buten-2-on；3-Cyclohexyl-3-buten-2-one
• CAS: 34970-11-1
• 化学式: C₁₀H₁₆O
• 分子量: 152.236
• InChiKey: DOIGQVHOESKDCD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 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-cyclohexylbut-3-en-2-one 在 盐酸羟胺 、 sodium carbonate 作用下， 以 甲醇 为溶剂， 反应 24.0h， 生成
  参考文献：
  名称：

  Expedient Access to 2,3-Dihydropyridines from Unsaturated Oximes by Rh(III)-Catalyzed C–H Activation

  摘要：

  alpha,beta-Unsaturated - oxime pivalates are proposed to undergo reversible C(sp(2))-H insertion with cationic Rh (III) complexes to furnish five-membered metallacycles. In the presence of 1,1-disubstituted olefins, these species participate in irreversible migratory insertion to give, after reductive elimination, 2,3-dihydropyridine products in good yields. Catalytic hydrogenation can then be used to. convert these molecules into piperidines, which are important structural components of numerous pharmaceuticals.

  DOI：

  10.1021/jacs.5b04946
• 作为产物：
  描述：

  环己基乙醛 在 四氢吡咯 、 manganese(IV) oxide 、 丙酸 作用下， 以 甲醇 、 乙醚 、 二氯甲烷 为溶剂， 反应 60.0h， 生成 3-cyclohexylbut-3-en-2-one
  参考文献：
  名称：

  Expedient Access to 2,3-Dihydropyridines from Unsaturated Oximes by Rh(III)-Catalyzed C–H Activation

  摘要：

  alpha,beta-Unsaturated - oxime pivalates are proposed to undergo reversible C(sp(2))-H insertion with cationic Rh (III) complexes to furnish five-membered metallacycles. In the presence of 1,1-disubstituted olefins, these species participate in irreversible migratory insertion to give, after reductive elimination, 2,3-dihydropyridine products in good yields. Catalytic hydrogenation can then be used to. convert these molecules into piperidines, which are important structural components of numerous pharmaceuticals.

  DOI：

  10.1021/jacs.5b04946

文献信息

• An Efficient Synthesis of α-Branched Enones
  作者：Stephen F. Martin、David A. Kummer、Jehrod B. Brenneman

  DOI：10.1055/s-2004-829095

  日期：——

  A new method for preparing α-branched enones from carboxylic acid derivatives is reported. The procedure commenced by the reaction of N,O-dimethylamides with a masked acyl anion equivalent, followed by the addition of (trimethylsilyl-methyl)cerium dichloride to give intermediates that undergo Lewis acid mediated olefination to produce enol ethers that are then hydrolyzed to afford simple α-branched

  报道了一种由羧酸衍生物制备α-支化烯酮的新方法。该过程开始于 N,O-二甲基酰胺与掩蔽的酰基阴离子等价物的反应，然后添加（三甲基甲硅烷基-甲基）二氯化铈得到中间体，该中间体经过路易斯酸介导的烯化生成烯醇醚，然后水解得到简单的α-支链烯酮，总产率高。
• Branching strategy in organic synthesis. A versatile ketone to enone homologation
  作者：Douglass F. Taber、Bruce P. Gunn

  DOI：10.1021/jo01317a033

  日期：1979.2
• Photochemical rearrangements of .alpha.-methylene ketones
  作者：Russell A. Cormier、William L. Schreiber、William C. Agosta

  DOI：10.1021/ja00796a019

  日期：1973.7
• TABER D. F.; GUNN B. P., J. ORG. CHEM., 1979, 44, NO 3, 450-452
  作者：TABER D. F.、 GUNN B. P.

  DOI：——

  日期：——
• Expedient Access to 2,3-Dihydropyridines from Unsaturated Oximes by Rh(III)-Catalyzed C–H Activation
  作者：Fedor Romanov-Michailidis、Kassandra F. Sedillo、Jamie M. Neely、Tomislav Rovis

  DOI：10.1021/jacs.5b04946

  日期：2015.7.22

  alpha,beta-Unsaturated - oxime pivalates are proposed to undergo reversible C(sp(2))-H insertion with cationic Rh (III) complexes to furnish five-membered metallacycles. In the presence of 1,1-disubstituted olefins, these species participate in irreversible migratory insertion to give, after reductive elimination, 2,3-dihydropyridine products in good yields. Catalytic hydrogenation can then be used to. convert these molecules into piperidines, which are important structural components of numerous pharmaceuticals.