Methyl 5,5-dichloro-3-oxo-4-pentenoate | 85839-23-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 酮酸及其衍生物
• 英文名称: Methyl 5,5-dichloro-3-oxo-4-pentenoate
• 英文别名: methyl 5,5-dichloro-3-oxopent-4-enoate
• CAS: 85839-23-2
• 化学式: C₆H₆Cl₂O₃
• 分子量: 197.01
• InChiKey: GPCRARQCGUBRIQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  11
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

文献信息

• Production of 5,5-disubstituted 3-oxo-pent-4-enoic acids, their halides, esters, thioesters and amides; and their use in antifungal and antibacterial compositions
  申请人：CIBA-GEIGY AG

  公开号：EP0067124A1

  公开（公告）日：1982-12-15

  A process is described for the production of a compound having the formula: R2R2C=CHCOCH2COZ I wherein R2 is fluorine, chlorine, or. bromine; R3 is hydrogen, fluorine, chlorine or bromine, or a group of formula -CR4R5R6 wherein R4, R5 and R6 are fluorine, chlorine or bromine; and Z is -AY or X1 wherein A is -O-, -S- or -NR7 wherein R7 is hydrogen, C1-10- straight - or branch chain alkyl or C3-4 straight or branch chain alkenyl, Y is hydrogen, C 1-18-straight or branch chain alkyl optionally interrrupted by one to five oxygen atoms and optionally substituted by one to five chlorine or bromine atoms, or by a group having the formula -OR8 or the formula -CO2R9 wherein R8 is hydrogen, C3-12-cycloalkyl, straight- or branch chain C3-18- alkenyl, C6-10-aryl or C7-13-aralkyl and R9 is hydrogen, C1-18- straight- or branch chain alkyl or straight- or branch chain C3-18- alkenyl, or Y is C3-18 straight or branch chain alkenyl, C3-18 straight- or branch chain alkynyl, C3-12-cycloalkyl, C7-13-aralkyl, or C6-10- aryl which is optionally substituted by one to three C1-9 straigth- or branch chain alkyl, halogen, nitro, CF3, or SO3H, or groups -OR10 wherein R10 is hydrogen or C1-4 straight or branch chain alkyl, provided that the total number of carbon atoms in the group -AY is from 0 to 20; or R7 and Y together may form a C2-7 polymethylene chain optionally substituted by one or two C1-4 alkyl groups and optionally interrupted by -0-, -S- or NR11 groups wherein R11 is C1-4 straight or branch chain alkyl; and X1 is C1 or Br; comprising (a) reacting, optionally in the presence of a solvent and an inorganic or organic acid - binding agent, a compound having the formula II: wherein R2 and R3 have their previous significance; R1 is fluorine, chlorine or bromine; and X is chlorine, bromine or iodine with the proviso that, when X is chlorine, none of R1, R2, R3, R4, R5 and R6 can be bromine; with a compound of formula H-Z III wherein Z has its previous significance; and (b) when Z is -AY and -AY is -OH, the product of step a) is optionally reacted with a compound IV capable of converting a carboxyl group into the corresponding carboxylic acid chloride or -bromide, thereby producing a compound of formula I wherein Z is- X1 as well as the use of the compounds of formula I in antifungal and antibacterial compositions.

  描述了一种具有以下式子的化合物的生产工艺：R2R2C=CHCOCH2COZ I 其中 R2 是氟、氯或溴；R3 是氢、氟、氯或溴，或式溴；R3 是氢、氟、氯或溴，或式 -CR4R5R6 的基团，其中 R4、R5 和 R6 是氟、氯或溴；Z是-AY或X1，其中A是-O-、-S-或-NR7，其中R7是氢、C1-10-直链或支链烷基或C3-4直链或支链烯基；Y是氢、C 1-18-直链或支链烷基，可选择被1-5个氧原子间断，并可选择被1-5个氯或溴原子取代、或具有式 -OR8 或式 -CO2R9 的基团，其中 R8 为氢、C3-12-环烷基、C3-18-直链或支链烯基、C6-10-芳基或 C7-13- 芳基，R9 为氢、C1-18 直链或支链烷基或 C3-18 直链或支链烯基，或 Y 是 C3-18 直链或支链烯基、C3-18 直链或支链炔基、C3-12-环烷基、C7-13-芳基、或 C6-10- 芳基，其任选被一至三个 C1-9 直链或支链烷基、卤素、硝基、CF3 或 SO3H 或基团 -OR10 取代，其中 R10 为氢或 C1-4 直链或支链烷基，条件是基团 -AY 中的碳原子总数为 0 至 20；或 R7 和 Y 一起可形成 C2-7 聚亚甲基链，该链可任选被一个或两个 C1-4 烷基取代，并可任选被-0-、-S-或 NR11 基团间断，其中 R11 为 C1-4 直链或支链烷基；以及 X1 为 C1 或 Br；包括 (a) 任选在溶剂和无机或有机酸结合剂存在下，使具有式 II： 其中 R2 和 R3 具有前述意义；R1 是氟、氯或溴；X 是氯、溴或碘，但当 X 是氯时，R1、R2、R3、R4、R5 和 R6 中不能有溴；(b) 当 Z 为-AY 且-AY 为-OH 时，步骤 a)的产物可选择与能将羧基转化为相应的羧酸氯化物或溴化物的化合物 IV 反应，从而生成式 I 化合物（其中 Z 为-X1）以及式 I 化合物在抗真菌和抗菌组合物中的用途。