2-(2-cyclohexen-1-yl)cyclohexane-1,3-dione | 121740-79-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(2-cyclohexen-1-yl)cyclohexane-1,3-dione
• 英文别名: 6-hydroxy-[1,1'-bi(cyclohexane)]-2',6-dien-2-one；2-Cyclohex-2-en-1-yl-3-hydroxycyclohex-2-en-1-one；2-cyclohex-2-en-1-yl-3-hydroxycyclohex-2-en-1-one
• CAS: 121740-79-2
• 化学式: C₁₂H₁₆O₂
• 分子量: 192.258
• InChiKey: DOWTVJDOXQKNRN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1,3-环己二酮 、 2-环己烯醇 在 palladium diacetate 1-金刚烷甲酸 、 三苯基膦 作用下， 以 水 为溶剂， 反应 0.5h， 以66%的产率得到2-(2-cyclohexen-1-yl)cyclohexane-1,3-dione
  参考文献：
  名称：

  Direct palladium/carboxylic acid-catalyzed C-allylation of cyclic 1,3-diones with allylic alcohols in water

  摘要：

  The direct activation of C-O bonds in allylic alcohols in water as a suspension medium by palladium complexes has been accelerated by carrying out the reactions in the presence of a carboxylic acid. The palladium-catalyzed allylation of cyclic 1,3-diones using allylic alcohols directly gave the corresponding C-allylated products in good yields. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.11.082

文献信息

• Palladium catalyzed c-allylation of highly acidic carbo and heterocyclic β-dicarbonyl compounds
  作者：M. Prat、M. Moreno-Mañas、J. Ribas

  DOI：10.1016/s0040-4020(01)86091-9

  日期：1988.1

  Highly acidic carbo and heterocyclic β-dicarbonyl compounds such as barbituric acid, 3,5-dimethyl-2-1,2,6-thiadiazine 1,1-dioxide, cyclohexane-1,3-dione, tetronic acids, Meldrum acid and 1,2-diphenylpyrazolidine-3,5-dione are efficiently C-allylated with primary and secondary allylating agents under palladium catalysis.

  高酸性碳和杂环β-二羰基化合物，例如巴比妥酸，3,5-二甲基-2 -1,2,6-噻二嗪1,1-二氧化物，环己烷-1,3-二酮，四氢代酸，Meldrum酸和1在钯催化下，用伯和仲烯丙基化剂有效地将2--二苯基吡唑烷-3,5-二酮进行C-烯丙基化。
• CoH-catalyzed radical hydroalkylation of alkenes with 1,3-dicarbonyls
  作者：Meihui Guan、Huanran Miao、Tao Qin、Ge Zhang、Qian Zhang

  DOI：10.1039/d2cc01382g

  日期：——

  useful reaction platform for alkene hydrofunctionalization with high chemoselectivity and predictable branched selectivity. However, MHAT-mediated hydrofunctionalization involves carbon–carbon bond formation still confined to carbon electrophiles. Here, we describe a mild, general, scalable, and functional group tolerant CoH-catalyzed intermolecular hydroalkylation of alkenes with 1,3-dicarbonyls. This

  金属氢化物氢原子转移 (MHAT) 催化已成为烯烃加氢官能化的有用反应平台，具有高化学选择性和可预测的支化选择性。然而，MHAT 介导的加氢官能​​化涉及的碳-碳键形成仍然局限于碳亲电子试剂。在这里，我们描述了一种温和的、通用的、可扩展的和官能团耐受的 CoH 催化的烯烃与 1,3-二羰基的分子间加氢烷基化。这种 CoH 催化的烯烃与碳亲核试剂的偶联代表了对 MHAT 引发的烯烃加氢官能化反应的重要补充。
• Direct palladium/carboxylic acid-catalyzed C-allylation of cyclic 1,3-diones with allylic alcohols in water
  作者：Kim-Hong Gan、Ciou-Jyu Jhong、Shyh-Chyun Yang

  DOI：10.1016/j.tet.2007.11.082

  日期：2008.2

  The direct activation of C-O bonds in allylic alcohols in water as a suspension medium by palladium complexes has been accelerated by carrying out the reactions in the presence of a carboxylic acid. The palladium-catalyzed allylation of cyclic 1,3-diones using allylic alcohols directly gave the corresponding C-allylated products in good yields. (c) 2007 Elsevier Ltd. All rights reserved.
• Activator-free and one-pot C-allylation by simple palladium catalyst in water
  作者：Yi-Jen Shue、Shyh-Chyun Yang

  DOI：10.1016/j.tetlet.2012.01.022

  日期：2012.3

  For atom economic and green chemistry concepts, we develop a reaction that involves one-pot and one step to construct the C-C bond without the help of any activating reagents for allylic alcohols in water. The palladium-catalyzed allylation of cyclic 1,3-diones using allylic alcohols directly gave the corresponding allylated products in 8-99% yields. (C) 2012 Elsevier Ltd. All rights reserved.