3-chloro-2-(2-nitrobenzoyl)-1,3-cyclohexadien-1-ol | 157034-90-7

• 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: 3-chloro-2-(2-nitrobenzoyl)-1,3-cyclohexadien-1-ol
• 英文别名: 3-Chloro-2-(2-nitro-benzoyl)-cyclohex-2-enone；3-chloro-2-(2-nitrobenzoyl)cyclohex-2-en-1-one
• CAS: 157034-90-7
• 化学式: C₁₃H₁₀ClNO₄
• 分子量: 279.68
• InChiKey: YFYHNUIHCYELLM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  80
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-chloro-2-(2-nitrobenzoyl)-1,3-cyclohexadien-1-ol 在 air 作用下， 生成 3-hydroxy-2-(2-nitrobenzoyl)cyclohex-2-en-1-one
  参考文献：
  名称：

  衍生自2-酰基-1,3-环己二酮的烯醇酯的异构化：机理和驱动力

  摘要：

  制备了一系列的2-酰基-1,3-环己二酮，并研究了相应的烯醇酯的异构化机理。这种迁移的驱动力可能是2-酰基氧原子和两个1,3-二酮氧之间的固有静电排斥力导致烯醇酯因平面度而变形，并导致其对烯醇化和随后的异构化的高度敏感性。

  DOI：

  10.1016/s0040-4039(03)00554-9
• 作为产物：
  描述：

  3-hydroxy-2-(2-nitrobenzoyl)cyclohex-2-en-1-one 在 草酰氯 作用下， 反应 3.0h， 以100%的产率得到3-chloro-2-(2-nitrobenzoyl)-1,3-cyclohexadien-1-ol
  参考文献：
  名称：

  Mode of Action of 4-Hydroxyphenylpyruvate Dioxygenase Inhibition by Triketone-type Inhibitors

  摘要：

  A series of 2-(2-nitrobenzoyl)cyclohexane-1,3-dione analogues (1-9) were designed, synthesized, and evaluated for inhibition of 4-hydroxyphenylpyruvate dioxygenase (4-HPPD), a key enzyme involved in the catabolism of tyrosine which catalyzes the conversion of 4-hydroxyphenylpyruvate to homogentisate. The correlations between the results of enzyme inhibition, ferric chloride tests, and the conformational analysis suggested that the tight binding between triketone-type inhibitors and 4-HPPD is likely due to chelation of the enzyme-bound ferric iron with the enol tautomer of 1,3-diketone moiety of the triketones. The presence of a 2-carbonyl group in the triketone is an essential structural feature for potent 4-HPPD inhibition. Modification of the 3-carbonyl group of triketone moiety to other functionality will reduce the overall planarity and thus prevent keto-enol tautomerization, resulting in a decrease or lack. of inhibition activity.

  DOI：

  10.1021/jm010568y

文献信息

• BENZOCYCLOHEXENONE, VERFAHREN ZU IHRER HERSTELLUNG UND IHRE VERWENDUNG ALS HERBIZIDE UND PFLANZENWACHSTUMGSREGULATOREN
  申请人：Hoechst Schering AgrEvo GmbH

  公开号：EP0673359A1

  公开（公告）日：1995-09-27
• [DE] BENZOCYCLOHEXENONE, VERFAHREN ZU IHRER HERSTELLUNG UND IHRE VERWENDUNG ALS HERBIZIDE UND PFLANZENWACHSTUMGSREGULATOREN<br/>[EN] BENZOYLCYCLOHEXENONES, METHODS OF PREPARING THEM AND THEIR USE AS HERBICIDES AND PLANT-GROWTH REGULATORS<br/>[FR] BENZOYLCYCLOHEXENONES, LEUR PROCEDE DE PREPARATION ET LEUR UTILISATION COMME HERBICIDES ET REGULATEURS DE CROISSANCE DES VEGETAUX
  申请人：——

  公开号：WO1994013619A1

  公开（公告）日：1994-06-23

  [EN] The invention concerns compounds of formula (I) in which n is 0 to 6; X represents halogen, CN, OCN, SCN, C2-C4 alkinyl or CHR<5>R<6>, R<5> and R<6>, independently of each other, being CN, NO2, formyl, optionally halo-substituted (C1-C4 alkyl)carbonyl, optionally halo-substituted (C1-C4 alkoxy)carbonyl or optionally substituted phenylcarbonyl; R<1> is optionally halo-substituted C1-C4 alkyl, optionally halo-substituted C3-C6 cycloalkyl or optionally substituted phenyl; R<2> represents halogen, CN, NO2, C1-C3 alkyl, C1-C3 alkoxy, C1-C3 haloalkyl, C1-C3 haloalkoxy or R<7>SOm-, R<7> being C1-C3 alkyl and m being 0, 1 or 2; R<3> represents H, halogen, OH, C1-C3 alkyl, C1-C3 alkoxy, C1-C3 haloalkyl, C1-C3 haloalkoxy or (C1-C3 alkoxy)carbonyl and R<4> represents H, CN, NO2, halogen, C1-C3 haloalkyl, C1-C3 haloalkoxy or R<8>S(O)p-, R<8> being C1-C3 alkyl and p being 0, 1 or 2. Such compounds are suitable for use as selective herbicides or plant-growth regulators. With the exception of compounds of formula (I) in which X = Cl, the compounds are also per se novel. They can be prepared from 2-benzoyl-1,3-cyclohexanediones by various methods.
  [FR] L'invention concerne les composés de la formule (I) qui s'utilisent comme herbicides sélectifs ou régulateurs de croissance des végétaux, dans laquelle n vaut entre 0 et 6, X désigne halogène, CN, OCN, SCN, alkynile C2-C4 ou CHR5R6, R5 et R6 désignant indépendamment l'un de l'autre CN, NO2, formyle, carbonyle (alkyle C1-C4) (halosubst.) ou carbonyle (alcoxy C1-C4) (halosubst.) ou phénylcarbonyle (subst.), R1 désigne alkyle C1-C4 (halosubst.), cycloalkyle C3-C6 (halosubst.) ou phényle (subst.), R2 désigne halogène, CN, NO2, alkyle C1-C3, alcoxy C1-C3, halogénure d'alcoyle C1-C3, halogénure d'alcoxy C1-C3 ou R7S(O)m, R7 désignant alkyle C1-C3 et m valant 0, 1 ou 2, R3 désigne H, halogène, OH, alkyle C1-C3, alcoxy C1-C3, halogénure d'alkyle C1-C3, halogénure d'alcoxy C1-C3 ou carbonyle (alcoxy C1-C3) et R4 désigne H, CN, NO2, halogène, halogénure d'alkyle C1-C3, halogénure d'alcoxy C1-C3 ou R8S(O)p-, R8 désignant alkyle C1-C3 et p valant 0, 1 ou 2. Abstraction faite des composés de la formule (I), où X = Cl, ces composés sont nouveaux en tant que tels. Il existe plusieurs manières de préparer des 2-benzoyl-1,3-cyclohexanediones.