5-Chloro-3-cyano-2-(1,1-dipropoxymethylenamino)thiophene | 272108-75-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 英文名称: 5-Chloro-3-cyano-2-(1,1-dipropoxymethylenamino)thiophene
• 英文别名: 5-chloro-2-(dipropoxymethylideneamino)thiophene-3-carbonitrile
• CAS: 272108-75-5
• 化学式: C₁₂H₁₅ClN₂O₂S
• 分子量: 286.782
• InChiKey: QJOCLDIRCAZKFV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  82.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  3-Cyano-2-(1,1-dipropoxymethylenamino) thiophene 在 吡啶 、 N-氯代丁二酰亚胺 作用下， 以 正己烷 、 水 、 乙酸乙酯 为溶剂， 生成 5-Chloro-3-cyano-2-(1,1-dipropoxymethylenamino)thiophene
  参考文献：
  名称：

  Novel pyrimidin-4-enamine as fungicide

  摘要：

  该专利涉及一种新型嘧啶衍生物，其化学式为I1，其中A是一个5-或6-成员环，可以是饱和或不饱和的，芳香或非芳香的，可以不含杂原子或含有1-3个杂原子O，S和/或N，每个原子可以是自由形式或盐形式；R1，R2和R3各自独立地是氢，卤素，C1-C8烷基，C2-C8烯基或C2-C8炔基，可以是未取代或单-三取代的C3-C6环烷基，卤素，C1-C6烷氧基，C1-C6烷硫基或C1-C6卤代烷氧基；O-C1-C6烷基，O-C2-C6烯基，O-C2-C6炔基，S-C1-C6烷基，S-C2-C6烯基或S-C2-C6炔基，可以是未取代或单-三取代的C3-C6环烷基，卤素，C1-C6烷氧基或C1-C6卤代烷氧基；氰基；硝基；或三甲基硅基；但是R1，R2和R3不能同时是氢；R4是C1-C8烷基，C2-C8烯基或C2-C8炔基，可以是未取代或单-三取代的C3-C6环烷基，卤素，氰基，硝基，CO-C1-C4烷基，COO-C1-C4烷基，CO-芳基，COO-芳基，C1-C6烷氧基或C1-C6卤代烷氧基；未取代或单-三取代的C3-C6环烷基，可以是C1-C6烷基，C1-C6卤代烷基，卤素，氰基，C1-C6烷氧基或C1-C6卤代烷氧基；苯基或苄基，其中苯基可以是未取代或单-五取代的卤素，氰基，硝基，C1-C8烷基，C2-C8烯基，C2-C8炔基，C1-C6烷氧基，C1-C6卤代烷氧基或C1-C6卤代烷基；NHR7；SR7或OR7；R5是C1-C8烷基，C2-C8烯基或C2-C8炔基，可以是未取代或单-三取代的C3-C6环烷基，卤素，氰基，硝基，CO-C1-C4烷基，COO-C1-C4烷基，CO-芳基，COO-芳基，C1-C6烷氧基，C1-C6烷硫基或C1-C6卤代烷氧基；未取代或单-三取代的C3-C6环烷基，可以是C1-C6烷基，卤素，氰基，C1-C6烷氧基，C1-C6卤代烷基或C1-C6卤代烷氧基；R6是氢，C1-C8烷基，C2-C8烯基或C2-C8炔基，可以是未取代或单-三取代的C3-C6环烷基，卤素，氰基，硝基，CO-C1-C4烷基，COO-C1-C4烷基，CO-芳基，COO-芳基，C1-C6烷氧基，C1-C6烷硫基或C1-C6卤代烷氧基；未取代或单-三取代的C3-C6环烷基，可以是C1-C6烷基，卤素，氰基，C1-C6烷氧基，C1-C6卤代烷基或C1-C6卤代烷氧基；O-C1-C6烷基，O-C2-C6烯基，O-C2-C6炔基，S-C1-C6烷基，S-C2-C6烯基或S-C2-C6炔基，可以是未取代或单-三取代的C3-C6环烷基，氰基，卤素，C1-C6烷氧基或C1-C6卤代烷氧基；芳基或杂芳基，可以是未取代或单-三取代的卤素，氰基，硝基，C1-C6烷基，C1-C6卤代烷基，C1-C6烷氧基或C1-C6卤代烷氧基；CO-C1-C6烷基；CO-C1-C6烷基-O-C1-C6烷基；CO-C1-C6卤代烷基；CO-杂芳基；SO2-C1-C6烷基；SO2-芳基；CO-苯基或CO-C1-C6烷基-O-苯基，其中苯基可以是未取代或单-三取代的卤素，氰基，硝基，C1-C6烷基，C1-C6卤代烷基，C1-C6烷氧基或C1-C6卤代烷氧基；COOR8，其中R8是C1-C8烷基，C2-C8烯基，C2-C8炔基，C3-C4环烷基或苯基，可以是未取代或单-三取代的卤素，氰基，硝基，C1-C6烷基，C1-C6卤代烷基，C1-C6烷氧基或C1-C6卤代烷氧基；氰基；硝基；或卤素；R7是C1-C8烷基，C2-C8烯基或C2-C8炔基，可以是未取代或单-三取代的C3-C6环烷基，卤素，氰基，硝基，CO-C1-C4烷基，COO-C1-C4烷基，CO-芳基，COO-芳基，C1-C6烷氧基，C1-C6烷硫基或C1-C6卤代烷氧基；未取代或单-三取代的C3-C6环烷基，可以是C1-C6烷基，C1-C6卤代烷基，卤素，氰基，C1-C6烷氧基或C1-C6卤代烷氧基；苯基或苄基，其中苯基可以是未取代或单-五取代的卤素，氰基，硝基，C1-C8烷基，C2-C8烯基，C2-C8炔基，C1-C6烷氧基，C1-C6卤代烷氧基或C1-C6卤代烷基。这些新化合物具有植物保护性能，适用于保护植物免受植物病原微生物和杀虫攻击的侵害。

  公开号：

  US20030040521A1

文献信息

• Pyrimidin-4-enamine as fungicide
  申请人：Syngenta Participations AG

  公开号：US06617330B2

  公开（公告）日：2003-09-09

  Novel pyrimidine derivatives of formula I as well as possible isomers and mixtures of isomers thereof. The novel compounds have plant-protective properties and are suitable for protecting plants against infestations by phytopathogenic microorganisms and insecticidal attack.

  化合物I的新型嘧啶衍生物及其可能的异构体和异构体混合物。这些新型化合物具有植物保护性能，适用于保护植物免受植物病原微生物和杀虫攻击的侵害。
• PYRIMIDIN-4-ENAMINE AS FUNGICIDE
  申请人：Syngenta Participations AG

  公开号：EP1124830A1

  公开（公告）日：2001-08-22
• US6617330B2
  申请人：——

  公开号：US6617330B2

  公开（公告）日：2003-09-09
• [EN] PYRIMIDIN-4-ENAMINE AS FUNGICIDE<br/>[FR] PYRIMIDIN-4-ENAMINE UTILISEE COMME FONGICIDE
  申请人：NOVARTIS AG

  公开号：WO2000031082A1

  公开（公告）日：2000-06-02

  Novel pyrimidine derivatives of formula (I), as well as possible isomers and mixtures of isomers thereof. The novel compounds have plant-protective properties and are suitable for protecting plants against infestations by phytopathogenic microorganisms and insecticidal attack.
• Novel pyrimidin-4-enamine as fungicide
  申请人：——

  公开号：US20030040521A1

  公开（公告）日：2003-02-27

  Novel pyrimidine derivatives of formula I 1 as well as possible isomers and mixtures of isomers thereof, wherein A is a 5- or 6-membered ring which may be saturated or unsaturated, aromatic or non-aromatic and which may contain no hetero atoms or 1-3 hetero atoms O, S and/or N, each in the free form or in salt form; R 1 , R 2 and R 3 are each independently of the other hydrogen; halogen; C 1 -C 8 alkyl, C 2 -C 8 alkenyl or C 2 -C 8 alkinyl which are unsubstituted or mono- to tri-substituted by C 3 -C 6 cycloalkyl, halogen, C 1 -C 6 alkoxy, C 1 -C 6 alkylthio or C 1 -C 6 haloalkoxy; O—C 1 -C 6 alkyl, O—C 2 -C 6 alkenyl, O—C 2 -C 6 alkynyl, S—C 1 -C 6 alkyl, S—C 2 -C 6 alkenyl or S—C 2 -C 6 alkynyl, which are unsubstituted or mono- to tri-substituted by C 3 -C 6 cycloalkyl, halogen, C 1 -C 6 alkoxy or C 1 -C 6 haloalkoxy; cyano; nitro; or trimethylsilyl; provided that R 1 , R 2 and R 3 are not hydrogen at the same time; R 4 is C 1 -C 8 alkyl, C 2 -C 8 alkenyl or C 2 -C 8 alkinyl which are unsubstituted or mono- to tri-substituted by C 3 -C 6 cycloalkyl, halogen, cyano, nitro, CO—C 1 -C 4 alkyl, COO—C 1 -C 4 alkyl, CO-aryl, COO-aryl, C 1 -C 6 alkoxy or C 1 -C 6 haloalkoxy; C 3 -C 6 cycloalkyl which is unsubstituted or mono- to tri-substituted by C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, halogen, cyano, C 1 -C 6 alkoxy or C 1 -C 6 haloalkoxy; phenyl or benzyl, in which the phenyl group is unsubstituted or mono- to pentasubstituted by halogen, cyano, nitro, C 1 -C 8 alkyl, C 2 -C 8 alkenyl, C 2 -C 8 alkinyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy or C 1 -C 6 haloalkyl; NHR 7 ; SR 7 or OR 7 ; R 5 is C 1 -C 8 alkyl, C 2 -C 8 alkenyl or C 2 -C 8 alkinyl which are unsubstituted or mono- to tri-substituted by C 3 -C 6 cycloalkyl, halogen, cyano, nitro, CO—C 1 -C 4 alkyl, COO—C 1 -C 4 alkyl, CO-aryl, COO-aryl, C 1 -C 6 alkoxy, C 1 -C 6 alkylthio or C 1 -C 6 haloalkoxy; C 3 -C 6 cycloalkyl which is unsubstituted or mono- to tri-substituted by C 1 -C 6 alkyl, halogen, cyano, C 1 -C 6 alkoxy, C 1 -C 6 haloalkyl or C 1 -C 6 haloalkoxy; R 6 is hydrogen; C 1 -C 8 alkyl, C 2 -C 8 alkenyl or C 2 -C 8 alkinyl which are unsubstituted or mono- to tri-substituted by C 3 -C 6 cycloalkyl, halogen, cyano, nitro, CO—C 1 -C 4 alkyl, COO—C 1 -C 4 alkyl, CO-aryl, COO-aryl, C 1 -C 6 alkoxy, C 1 -C 6 alkylthio or C 1 -C 6 haloalkoxy; C 3 -C 6 cycloalkyl which is unsubstituted or mono- to tri-substituted by C 1 -C 6 alkyl, halogen, cyano, C 1 -C 6 alkoxy, C 1 -C 6 haloalkyl or C 1 -C 6 haloalkoxy; O—C 1 -C 6 alkyl, O—C 2 -C 6 alkenyl, O—C 2 -C 6 alkynyl, S—C 1 -C 6 alkyl, S—C 2 -C 6 alkenyl or S—C 2 -C 6 alkynyl, which are unsubstituted or mono- to tri-substituted by C 3 -C 6 cycloalkyl, cyano, halogen, C 1 -C 6 alkoxy or C 1 -C 6 haloalkoxy; aryl or heteroaryl which are unsubstituted or mono- to tri-substituted by halogen, cyano, nitro, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy or C 1 -C 6 haloalkoxy; CO—C 1 -C 6 alkyl; CO—C 1 -C 6 alkyl-O—C 1 -C 6 alkyl; CO—C 1 -C 6 haloalkyl; CO-heteroaryl; SO 2 —C 1 -C 6 alkyl; SO 2 -aryl; CO-phenyl or CO—C 1 -C 6 alkyl-O-phenyl in which phenyl is unsubstituted or mono- to tri-substituted by halogen, cyano, nitro, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy or C 1 -C 6 haloalkoxy; COOR 8 wherein R 8 is C 1 -C 8 alkyl, C 2 -C 8 alkenyl, C 2 -C 8 alkinyl, C 3 -C 4 cycloalkyl or phenyl which is unsubstituted or mono- to tri-substituted by halogen, cyano, nitro, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy or C 1 -C 6 haloalkoxy; cyano; nitro; or halogen; and R 7 is C 1 -C 8 alkyl, C 2 -C 8 alkenyl or C 2 -C 8 alkinyl which are unsubstituted or mono- to tri-substituted by C 3 -C 6 cycloalkyl, halogen, cyano, nitro, CO—C 1 -C 4 alkyl, COO—C 1 -C 4 alkyl, CO-aryl, COO-aryl, C 1 -C 6 alkoxy, C 1 -C 6 alkylthio or C 1 -C 6 haloalkoxy; C 3 -C 6 cycloalkyl which is unsubstituted or mono- to tri-substituted by C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, halogen, cyano, C 1 -C 6 alkoxy or C 1 -C 6 haloalkoxy; phenyl or benzyl, in which the phenyl group is unsubstituted or mono- to pentasubstituted by halogen, cyano, nitro, C 1 -C 8 alkyl, C 2 -C 8 alkenyl, C 2 -C 8 alkinyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy or C 1 -C 6 haloalkyl. The novel compounds have plant-protective properties and are suitable for protecting plants against infestations by phytopathogenic microorganisms and insecticidal attack.

  该专利涉及一种新型嘧啶衍生物，其化学式为I1，其中A是一个5-或6-成员环，可以是饱和或不饱和的，芳香或非芳香的，可以不含杂原子或含有1-3个杂原子O，S和/或N，每个原子可以是自由形式或盐形式；R1，R2和R3各自独立地是氢，卤素，C1-C8烷基，C2-C8烯基或C2-C8炔基，可以是未取代或单-三取代的C3-C6环烷基，卤素，C1-C6烷氧基，C1-C6烷硫基或C1-C6卤代烷氧基；O-C1-C6烷基，O-C2-C6烯基，O-C2-C6炔基，S-C1-C6烷基，S-C2-C6烯基或S-C2-C6炔基，可以是未取代或单-三取代的C3-C6环烷基，卤素，C1-C6烷氧基或C1-C6卤代烷氧基；氰基；硝基；或三甲基硅基；但是R1，R2和R3不能同时是氢；R4是C1-C8烷基，C2-C8烯基或C2-C8炔基，可以是未取代或单-三取代的C3-C6环烷基，卤素，氰基，硝基，CO-C1-C4烷基，COO-C1-C4烷基，CO-芳基，COO-芳基，C1-C6烷氧基或C1-C6卤代烷氧基；未取代或单-三取代的C3-C6环烷基，可以是C1-C6烷基，C1-C6卤代烷基，卤素，氰基，C1-C6烷氧基或C1-C6卤代烷氧基；苯基或苄基，其中苯基可以是未取代或单-五取代的卤素，氰基，硝基，C1-C8烷基，C2-C8烯基，C2-C8炔基，C1-C6烷氧基，C1-C6卤代烷氧基或C1-C6卤代烷基；NHR7；SR7或OR7；R5是C1-C8烷基，C2-C8烯基或C2-C8炔基，可以是未取代或单-三取代的C3-C6环烷基，卤素，氰基，硝基，CO-C1-C4烷基，COO-C1-C4烷基，CO-芳基，COO-芳基，C1-C6烷氧基，C1-C6烷硫基或C1-C6卤代烷氧基；未取代或单-三取代的C3-C6环烷基，可以是C1-C6烷基，卤素，氰基，C1-C6烷氧基，C1-C6卤代烷基或C1-C6卤代烷氧基；R6是氢，C1-C8烷基，C2-C8烯基或C2-C8炔基，可以是未取代或单-三取代的C3-C6环烷基，卤素，氰基，硝基，CO-C1-C4烷基，COO-C1-C4烷基，CO-芳基，COO-芳基，C1-C6烷氧基，C1-C6烷硫基或C1-C6卤代烷氧基；未取代或单-三取代的C3-C6环烷基，可以是C1-C6烷基，卤素，氰基，C1-C6烷氧基，C1-C6卤代烷基或C1-C6卤代烷氧基；O-C1-C6烷基，O-C2-C6烯基，O-C2-C6炔基，S-C1-C6烷基，S-C2-C6烯基或S-C2-C6炔基，可以是未取代或单-三取代的C3-C6环烷基，氰基，卤素，C1-C6烷氧基或C1-C6卤代烷氧基；芳基或杂芳基，可以是未取代或单-三取代的卤素，氰基，硝基，C1-C6烷基，C1-C6卤代烷基，C1-C6烷氧基或C1-C6卤代烷氧基；CO-C1-C6烷基；CO-C1-C6烷基-O-C1-C6烷基；CO-C1-C6卤代烷基；CO-杂芳基；SO2-C1-C6烷基；SO2-芳基；CO-苯基或CO-C1-C6烷基-O-苯基，其中苯基可以是未取代或单-三取代的卤素，氰基，硝基，C1-C6烷基，C1-C6卤代烷基，C1-C6烷氧基或C1-C6卤代烷氧基；COOR8，其中R8是C1-C8烷基，C2-C8烯基，C2-C8炔基，C3-C4环烷基或苯基，可以是未取代或单-三取代的卤素，氰基，硝基，C1-C6烷基，C1-C6卤代烷基，C1-C6烷氧基或C1-C6卤代烷氧基；氰基；硝基；或卤素；R7是C1-C8烷基，C2-C8烯基或C2-C8炔基，可以是未取代或单-三取代的C3-C6环烷基，卤素，氰基，硝基，CO-C1-C4烷基，COO-C1-C4烷基，CO-芳基，COO-芳基，C1-C6烷氧基，C1-C6烷硫基或C1-C6卤代烷氧基；未取代或单-三取代的C3-C6环烷基，可以是C1-C6烷基，C1-C6卤代烷基，卤素，氰基，C1-C6烷氧基或C1-C6卤代烷氧基；苯基或苄基，其中苯基可以是未取代或单-五取代的卤素，氰基，硝基，C1-C8烷基，C2-C8烯基，C2-C8炔基，C1-C6烷氧基，C1-C6卤代烷氧基或C1-C6卤代烷基。这些新化合物具有植物保护性能，适用于保护植物免受植物病原微生物和杀虫攻击的侵害。