2-[Hydroxy(phenyl)methylene]-1,3-cyclohexanedione | 61834-43-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-[Hydroxy(phenyl)methylene]-1,3-cyclohexanedione
• 英文别名: 2-benzoylcyclohexane-1,3-dione；2-benzoyl-3-hydroxycyclohex-2-en-1-one
• CAS: 61834-43-3
• 化学式: C₁₃H₁₂O₃
• 分子量: 216.236
• InChiKey: ZRAFFOXPOZNBEI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.43
• 重原子数：
  16.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  54.37
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  2-[Hydroxy(phenyl)methylene]-1,3-cyclohexanedione 在 mercury(II) diacetate 、 sodium acetate 作用下， 以 溶剂黄146 为溶剂， 以45%的产率得到benzoyl-resorcinol
  参考文献：
  名称：

  Synthesis of 1-(2,6-Dihydroxyphenyl)-1-alkanones and Benzophenone by Aromatization of 2-Acyl-3-hydroxy-2-cyclohexene-1-ones with Mercuric Acetate

  摘要：

  1-(2,6-二羟基苯基)-1-烷酮是从昆虫和药用植物中发现的天然产物，可以很容易地从 1,3-环己二酮和适当的羧酸中制备出来。最后一步是使用乙酸汞进行芳香化。

  DOI：

  10.1055/s-1990-27107
• 作为产物：
  描述：

  1,3-环己二酮 、 苯甲酰氯 在 potassium cyanide 、 三乙胺 作用下， 以 乙腈 为溶剂， 生成 2-[Hydroxy(phenyl)methylene]-1,3-cyclohexanedione
  参考文献：
  名称：

  NMR and computational studies on tautomerism of 3-hydroxy-2-(2-thienylcarbonyl)cyclohex-2-en-1-one

  摘要：

  The tautomeric system of 3-hydroxy-2-(2-thienylcarbonyl)cyclohex-2-en-1-one 1 has been investigated by NMR spectroscopy between 224 and 298 K. At all temperatures an endocyclic enol tautomer was the major isomer; however, at low temperatures two other enol isomers were found. Conformational search of the potential energy surfaces of all tautomers of cyclohexenone 1 was also carried out. Extensive calculations were performed for two triketones and four cis-endocyclic double bond enol tautomers with the lowest energies. Syntheses of 3-methoxy-2-(2-thienylcarbonyl)cyclohex-2-en-1-one 2 and 2-benzoy1-3hydroxycyclohex-2-en-1-one 3 were carried out to analyze the features of thienyl group rotation and structural differences with a symmetrical substituent, respectively. (C) 2013 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molstruc.2013.11.057

文献信息

• Reaction of 2-aroylcyclohex-2-enones with hydroxylamine. Isoxazole ring formation.
  作者：YASUMITSU TAMURA、MINAKO INOUE、AKIMORI WADA、MASANOBU FUJITA、YASUYUKI KITA

  DOI：10.1248/cpb.29.3226

  日期：——

  A novel one-step and high-yield isoxazole formation of 2-aroylcyclohex-2-enones is described. Treatment of such an enone with hydroxylamine under acidic conditions (NH2OH·HCl in EtOH) gave the corresponding 3-aryl-6, 7-dihydro [2, 1] benzisoxazole. Changes in the reaction conditions caused marked changes in the course of the reaction. A possible mechanism for these reactions is put forward.

  描述了一种新颖的一步法高收率异噁唑形成2-芳基环己-2-烯酮的方法。在酸性条件下（乙醇中的NH2OH·HCl）用羟胺处理这种烯酮，得到相应的3-芳基-6,7-二氢[2,1]苯并异噁唑。反应条件的变化导致反应过程发生显著变化。提出了这些反应的可能机理。
• Synthesis of 1-(2,6-Dihydroxyphenyl)-1-alkanones and Benzophenone by Aromatization of 2-Acyl-3-hydroxy-2-cyclohexene-1-ones with Mercuric Acetate
  作者：James E. Oliver、Kenneth R. Wilzer、Rolland M. Waters

  DOI：10.1055/s-1990-27107

  日期：——

  1-(2,6-Dihydroxyphenyl)-1-alkanones, natural products identified from insects and from medicinal plants, are readily prepared from 1,3-cyclohexanedione and appropriate carboxylic acids. The final step involves aromatization using mercuric acetate.

  1-(2,6-二羟基苯基)-1-烷酮是从昆虫和药用植物中发现的天然产物，可以很容易地从 1,3-环己二酮和适当的羧酸中制备出来。最后一步是使用乙酸汞进行芳香化。
• [EN] 2-BENZOYLCYCLOHEXANE-1,3-DIONE COMPOUNDS AND THEIR USE AS HERBICIDES<br/>[FR] COMPOSES DE 2-BENZOCYCLOHEXANE-1,3-DIONE ET LEUR UTILISATION COMME HERBICIDES
  申请人：DOW AGROSCIENCES LLC

  公开号：WO1998042648A1

  公开（公告）日：1998-10-01

  (EN) 2-Benzoylcyclohexane-1,3-dione compounds in which the benzoyl moiety is substituted in the 2-position with groups such as halo or alkyl, in the 4-position with an alkylsulfonyl group, and in the 3-position with an acyclic or cyclic derivatized amino group, such as 2-(2-chloro-4-methylsulfonyl-3-(morpholin-4-yl)benzoyl)-5,5-dimethylcyclohexane-1,3-dione, were prepared and found to be useful for the control of a variety of broad-leaf and grassy weeds. The compounds can be applied either preemergently or postemergently and can be used to control undesirable vegetation in corn, rice, and wheat crops.(FR) L'invention porte sur des composés de 2-benzoylcyclohexane-1,3-dione dans lesquels la fraction benzoyl est substituée en position 2 par des groupes tels que halo ou alkyle, en position 4 par un groupe alkylsulfonyle et en position 3 par un groupe amino dérivatisé, acyclique ou cyclique, tel que (2-(2-chloro-4-méthylsulfonyl-3-(morpholin-4-yl)benzoyl)-5,5-diméthylcyclohexane-1,3-dione. La préparation de ces composés s'est avérée utile dans l'élimination des dicotylédones et des mauvaises herbes graminées.

  这些2-苯甲基环己烷-1,3-二酮类化合物被制备出来，其中苯甲基群在2位取代以卤素或烷基，在4位取代以甲基硫基，而3位取代以acyclic或cyclic derivatised氨基基团，例如2-(2-氯-4-甲基硫基-3-(多环半式环-4-位)的苯甲基)-5,5-二甲基环己烷-1,3-二酮。这些化合物可以用于预除 unforeseen 灌木丛和草地杂草的生长，在玉米、水稻和小麦作物中可被用来控制不希望生长的植被。
• OLIVER, JAMES E.;WILZER, KENNETH R.;WATERS, ROLLAND M., SYNTHESIS,(1990) N2, C. 1117-1119
  作者：OLIVER, JAMES E.、WILZER, KENNETH R.、WATERS, ROLLAND M.

  DOI：——

  日期：——
• TAMURA, YASUMITSU;INOUE, MINAKO;WADA, AKIMORI;FUJITA, MASANOBU;KITA, YASU+, CHEM. AND PHARM. BULL., 1981, 29, N 11, 3226-3231
  作者：TAMURA, YASUMITSU、INOUE, MINAKO、WADA, AKIMORI、FUJITA, MASANOBU、KITA, YASU+

  DOI：——

  日期：——