5-chloromethyl-2,3-pyridine dicarboxylic acid anhydride | 124523-80-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 5-chloromethyl-2,3-pyridine dicarboxylic acid anhydride
• 英文别名: 5-chloromethyl-2,3-pyridinedicarboxylic acid anhydride；5-chloromethyl-pyridine-2,3-carboxylic acid anhydride；3-(chloromethyl)-Furo[3,4-b]pyridine-5,7-dione；3-(chloromethyl)furo[3,4-b]pyridine-5,7-dione
• CAS: 124523-80-4
• 化学式: C₈H₄ClNO₃
• 分子量: 197.578
• InChiKey: JLJSCLYUDCQETH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  56.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-chloromethyl-2,3-pyridine dicarboxylic acid anhydride 在 sodium methylate 、 三乙胺 作用下， 以 甲醇 、 乙腈 为溶剂， 生成 5-methoxymethyl-2-(4-isopropyl-4-methyl-5-oxo-2-imidazolin-2 yl)nicotinic acid, triethylamine salt
  参考文献：
  名称：

  5 (and/or 6) substituted 2-(2-imidazolin-2-yl)nicotinic acids, esters

  摘要：

  提供了新型的5(和/或6)取代的2-(2-咪唑啉-2-基)和2-(2-咪唑啉基)烟酸、酯和盐，它们可用作除草剂。同时还提供了新型的取代吡咯吡啶乙腈、吡咯吡啶乙酰胺、咪唑吡咯吡啶二酮和氨基甲酰烟酸酯，它们可用作上述除草剂的中间体。

  公开号：

  US05334576A1
• 作为产物：
  描述：

  5-methylpyridine-2,3-dicarboxylic anhydride 在 磺酰氯 、 偶氮二异丁腈 作用下， 以 邻二氯苯 为溶剂， 反应 2.25h， 以61%的产率得到5-chloromethyl-2,3-pyridine dicarboxylic acid anhydride
  参考文献：
  名称：

  [EN] PROCESS FOR MANUFACTURING 5-CHLOROMETHYL-2,3-PYRIDINE DICARBOXYLIC ACID ANHYDRIDES
  [FR] PROCEDE DE FABRICATION DE 5-CHLOROMETHYL-2,3-PYRIDINE D'ANHYDRIDES D'ACIDE DICARBOXYLIQUE

  摘要：

  一种制造5-氯甲基-2,3-吡啶二甲酸酐（I）的方法，其中Z是氢或卤素; Z1是氢，卤素，氰基或硝基; 包括以下步骤：（i）将式（II）的化合物与氯化剂反应，其中符号具有式（I）中给出的含义，可选地在卤代烃溶剂中，在自由基引发剂的存在下，（ii）从氯苯，1,2-二氯苯，1,3-二氯苯，1,4-二氯苯，二氯乙烷，三氯甲烷，二氯甲烷，甲苯，二甲苯，乙酸乙酯，甲基叔丁基醚和其混合物中选择的溶剂中结晶化步骤（i）中形成的化合物（I）。化合物（I）是合成除草剂咪唑烷酮的有用中间体。

  公开号：

  WO2010054954A1

文献信息

• [EN] 2-[(1-CYANOPROPYL)CARBAMOYL]-5-CHLOROMETHYL NICOTINIC ACIDS AND THE USE THEREOF IN MANUFACTURING HERBICIDAL IMIDAZOLINONES<br/>[FR] ACIDES 2-[(1-CYANOPROPYL)CARBAMOYL]-5-CHLOROMÉTHYLNICOTINIQUES ET LEUR UTILISATION DANS LA FABRICATION D'IMIDAZOLINONES HERBICIDES
  申请人：BASF SE

  公开号：WO2010054952A1

  公开（公告）日：2010-05-20

  2-[(1-cyanopropyl)carbamoyl]-5-chloromethyl nicotinic acids of formula (I) where Z is hydrogen or halogen; Z1 is hydrogen, halogen, cyano or nitro; R1 is C1-C4 alkyl; R2 is C1-C4 alkyl, C3-C6 cycloalkyl or R1 and R2, when taken together with the atom to which they are attached, represent a C3-C6 cycloalkyl group optionally substituted with methyl, and R3 is hydrogen or a cation preferably selected from the group consisting of alkali metals, alkaline earth metals, manganese, copper, iron, zinc, cobalt, lead, silver, nickel, ammonium and organic ammonium; are useful intermediates for the synthesis of herbicidal imidazolinones.

  式(I)中，Z是氢或卤素；Z1是氢、卤素、氰基或硝基；R1是C1-C4烷基；R2是C1-C4烷基、C3-C6环烷基或R1和R2，当它们与它们所连接的原子一起取代时，表示可选地用甲基取代的C3-C6环烷基；R3是氢或阳离子，优选从含有碱金属、碱土金属、锰、铜、铁、锌、钴、铅、银、镍、铵和有机铵的群中选择；这些化合物是合成除草剂咪唑烷酮的有用中间体。
• 2-[1-Cyanopropyl)Carbamoyl]-5-Chloromethyl Nicotinic Acids and the Use Thereof in Manufacturing Herbicidal Imidazolinones
  申请人：Menges Frederik

  公开号：US20110218340A1

  公开（公告）日：2011-09-08

  2-[(1-cyanopropyl)carbamoyl]-5-chloromethyl nicotinic acids of formula (I) where Z is hydrogen or halogen; Z 1 is hydrogen, halogen, cyano or nitro; R 1 is C 1 -C 4 alkyl; R 2 is C 1 -C 4 alkyl, C 3 -C 6 cycloalkyl or R 1 and R 2 , when taken together with the atom to which they are attached, represent a C 3 -C 6 cycloalkyl group optionally substituted with methyl, and R 3 is hydrogen or a cation preferably selected from the group consisting of alkali metals, alkaline earth metals, manganese, copper, iron, zinc, cobalt, lead, silver, nickel, ammonium and organic ammonium; are useful intermediates for the synthesis of herbicidal imidazolinones.

  式(I)中，Z为氢或卤素；Z1为氢、卤素、氰或硝基；R1为C1-C4烷基；R2为C1-C4烷基、C3-C6环烷基或R1和R2，当它们与它们附着的原子一起取时，表示可选地用甲基取代的C3-C6环烷基；R3为氢或阳离子，优选从选自碱金属、碱土金属、锰、铜、铁、锌、钴、铅、银、镍、铵和有机铵的群中选择；是制备除草剂咪唑烷酮的有用中间体。
• Process for Manufacturing 5-Chloromethyl-2,3-Pyridine Dicarboxylic Acid Anhydrides
  申请人：Menges Frederik

  公开号：US20110224439A1

  公开（公告）日：2011-09-15

  A process for manufacturing 5-chloromethyl-2,3-pyridine dicarboxylic acid anhydrides (I) wherein Z is hydrogen or halogen; Z 1 is hydrogen, halogen, cyano or nitro; comprising the steps of (i) reacting a compound of formula (II), wherein the symbols have the meaning given in formula (I), with a chlorinating agent, optionally in the presence of a radical initiator in a solvent selected from halogenated hydrocarbons, and (ii) crystallizing the compound (I) formed in step (i) from a solvent selected from chlorobenzene, 1,2-dichlorobenzene, 1,3-dichlorobenzene, 1,4-dichlorobenzene, dichloroethane, trichloromethane, dichloromethane, toluene, xylenes, ethyl acetate, methyl tert.-butyl ether, and mixtures thereof. Compounds (I) are useful intermediates in the synthesis of herbicidal imidazolinones.

  一种制造5-氯甲基-2,3-吡啶二羧酸酐（I）的过程，其中Z为氢或卤素；Z1为氢，卤素，氰基或硝基；包括以下步骤：（i）将式（II）的化合物与氯化剂反应，其中符号具有式（I）中给出的含义，可选地在卤代烃溶剂中加入自由基引发剂，以及（ii）从氯苯，1,2-二氯苯，1,3-二氯苯，1,4-二氯苯，二氯乙烷，三氯甲烷，二氯甲烷，甲苯，二甲苯，乙酸乙酯，甲基叔丁基醚和其混合物中选择的溶剂中结晶化步骤（i）中形成的化合物（I）。化合物（I）在杂草除草剂咪唑烷酮的合成中是有用的中间体。
• Process for Manufacturing 5-Formyl-Pyridine-2,3-Dicarboxylic Acid Esters
  申请人：Rack Michael

  公开号：US20110245505A1

  公开（公告）日：2011-10-06

  A process for manufacturing a 5-formyl-pyridine-2,3-dicarboxylic acid ester (I) wherein Z is hydrogen or halogen; Z 1 is hydrogen, halogen, cyano or nitro and R 1 , R 2 are independently C 1 -C 10 -alkyl, comprising the steps of (i) reacting a compound of formula (II), wherein the symbols are as in formula (I), with a nitrosation agent (III) R 3 —O—N═O (III) wherein R 3 is C 1 -C 8 -alkyl, in the presence of an alkali metal or alkaline earth metal alcoholates or carbonates in a polar aprotic solvent at a temperature of from −45 to 40° C., to obtain an oxime compound (IV) where Z, Z 1 , R 1 and R 2 are as in formula (I), and (ii) reacting oxime compound (IV) with an aliphatic C 1 -C 10 -aldehyde in the presence of a Lewis acid at a temperature in the range of from 0 to 100° C. The compounds of formula (I) are useful intermediates in the synthesis of herbicidal imidazolinones, like imazamox.

  一种制造5-甲酰基吡啶-2,3-二羧酸酯（I）的过程，其中Z为氢或卤素; Z1为氢，卤素，氰或硝基，R1，R2独立地为C1-C10烷基，包括以下步骤：（i）在极性无水溶剂中，在-45至40℃的温度下，将式（II）的化合物与亚硝酰化试剂（III）R3-O-N═O（III）反应，其中符号如式（I）中所示，存在碱金属或碱土金属醇盐或碳酸盐，以获得肟化合物（IV），其中Z，Z1，R1和R2如式（I）中所示，（ii）在0至100℃的温度下，在路易斯酸的存在下，将肟化合物（IV）与脂肪族C1-C10醛反应。式（I）的化合物是合成除草剂咪唑烷酮（如咪唑草胺）的有用中间体。
• 2-[1-cyanopropyl)carbamoyl]-5-chloromethyl nicotinic acids and the use thereof in manufacturing herbicidal imidazolinones
  申请人：Menges Frederik

  公开号：US08563734B2

  公开（公告）日：2013-10-22

  2-[(1-cyanopropyl)carbamoyl]-5-chloromethyl nicotinic acids of formula (I) where Z is hydrogen or halogen; Z1 is hydrogen, halogen, cyano or nitro; R1 is C1-C4 alkyl; R2 is C1-C4 alkyl, C3-C6 cycloalkyl or R1 and R2, when taken together with the atom to which they are attached, represent a C3-C6 cycloalkyl group optionally substituted with methyl, and R3 is hydrogen or a cation preferably selected from the group consisting of alkali metals, alkaline earth metals, manganese, copper, iron, zinc, cobalt, lead, silver, nickel, ammonium and organic ammonium; are useful intermediates for the synthesis of herbicidal imidazolinones.

  式(I)中，Z为氢或卤素；Z1为氢，卤素，氰或硝基；R1为C1-C4烷基；R2为C1-C4烷基，C3-C6环烷基或当它们与它们连接的原子一起取时，表示一个C3-C6环烷基，可选地用甲基取代；R3为氢或阳离子，优选为从碱金属，碱土金属，锰，铜，铁，锌，钴，铅，银，镍，铵和有机铵组成的群中选择的阳离子。这些化合物是除草剂咪唑烷酮的合成中间体。