N-thienyl-3 formamide | 59445-90-8

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N-thienyl-3 formamide
• 英文别名: N-(Thienyl-3)-formamid；3-Formylaminothiophen；N-(thiophen-3-yl)formamide；3-Formylamino-thiophene；N-thiophen-3-ylformamide
• CAS: 59445-90-8
• 化学式: C₅H₅NOS
• 分子量: 127.167
• InChiKey: VFVKYXLBGMFNMB-UHFFFAOYSA-N

物化性质

• 沸点：
  293.8±13.0 °C(Predicted)
• 密度：
  1.328±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  8
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  57.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-thienyl-3 formamide 在 aluminum oxide 、 potassium fluoride 、 lithium aluminium tetrahydride 作用下， 以 乙醚 、 乙腈 为溶剂， 反应 4.0h， 生成 N,N-dimethyl thienyl-3 amine
  参考文献：
  名称：

  Outurquin, Francis; Lerouge, Patrice; Paulmier, Claude, Bulletin de la Societe Chimique de France, 1986, # 2, p. 259 - 266

  摘要：

  DOI：
• 作为产物：
  描述：

  3-氨基噻吩 、 甲酸乙酯 在 sodium hydride 作用下， 以 四氢呋喃 、 mineral oil 为溶剂， 反应 24.0h， 以97%的产率得到N-thienyl-3 formamide
  参考文献：
  名称：

  Reactions of ortho-Lithiophenyl (-Hetaryl) Isocyanides with Carbonyl Compounds: Rearrangements of 2-Metalated 4H-3,1-Benzoxazines

  摘要：

  ortho-Lithiophenyl (-hetaryl) isocyanides react with aldehydes and ketones providing isocyanoalcohols 8 (36-89%, nine examples), 4H-3,1-benzoxazines 9 (45-78%, six examples) or, after two types of rearrangements, isobenzofuran-1(3H)-imines (iminophthalanes) 18 (52-75%, four examples), or indolin-2-ones 19 (42-79%, two. examples), depending on the reaction conditions and substitution patterns. Isocyanoalcohols 8, in turn, were converted to 9 or 18 under Cu(I) catalysis (66-86%, eight examples). 4H-3, 1-Benzoxazin-4-ones 39-Nu and isatoic anhydride 40 were obtained by the reaction of 2 with carbon dioxide followed by trapping of the lithiated intermediate with iodine and subsequent reactions with nucleophiles (45-60%, three examples).

  DOI：

  10.1021/jo9004734

文献信息

• 3-Carbonylaminothiophenes and their use as fungicides
  申请人：Ehrenfreund Josef

  公开号：US20060276434A1

  公开（公告）日：2006-12-07

  The invention also relates to novel compounds of formula (I) where Het is a 5- or 6-membered heterocyclic ring containing one to three heteroatoms, each independently selected from oxygen, nitrogen and sulphur, the ring being substituted by one to three groups R 4 ; R 1 is hydrogen, optionally substituted (C 1-4 )alkyl, formyl, optionally substituted (C 1-4 )alkylC(═O), optionally substituted (C 1-4 )alkylC(═O)O, optionally substituted (C 1-4 )alkoxy(C 1-4 )alkyl, optionally substituted allyl, optionally substituted propargyl or optionally substituted allenyl; each R 2 is, independently, halogen, optionally substitute (C 1-4 )alkyl, optionally substituted (C 1-4 )alkoxy or optionally substituted (C 1-4 )alkoxy(C 1-4 )alkyl; R 3 is either position 2 or at position 4 of the thiophene ring and is an organic group containing three to thirteen carbon atoms and al least one silicon atom and, optionally, one to three heteroatoms, each independently selected from oxygen, nitrogen and sulphur, and is optionally substituted by one to four independently selected halogen atoms; each R 4 is, independently, halogen, C 1-3 alkyl, C 1-3 haloalkyl, C 1-3 alkoxy(C 1-3 )alkyl or cyano; r is 0, 1 or 2; and X is O or S; or an N-oxide thereof, to novel intermediates used in the preparation of these compounds, to agrochemical compositions which comprise at least one of the novel compounds as an active ingredient and to the use of the active ingredients or compositions in agriculture or horticulture for controlling or preventing infestation of plants by phytopathogenic microorganisms, preferably fungi.

  本发明涉及式（I）的新化合物，其中Het是一个含有1-3个杂原子的5-或6元杂环，每个杂原子可以独立地选择氧、氮和硫，该环被1-3个R4基团取代；R1是氢、可选取代的（C1-4）烷基、甲酰基、可选取代的（C1-4）烷基C（═O）、可选取代的（C1-4）烷基C（═O）O、可选取代的（C1-4）烷氧基（C1-4）烷基、可选取代的烯丙基、可选取代的丙炔基或可选取代的芳烃基；每个R2独立地是卤素、可选取代的（C1-4）烷基、可选取代的（C1-4）烷氧基或可选取代的（C1-4）烷氧基（C1-4）烷基；R3在噻吩环的2位或4位，是一个有机基团，含有3-13个碳原子和至少一个硅原子，还可以含有1-3个杂原子，每个杂原子可以独立地选择氧、氮和硫，可以被1-4个独立选择的卤素基团取代；每个R4独立地是卤素、C1-3烷基、C1-3卤代烷基、C1-3烷氧基（C1-3）烷基或氰基；r为0、1或2；X为O或S；或其N-氧化物。本发明还涉及用于制备这些化合物的新中间体，以及至少包含一种新化合物作为活性成分的农药组合物，以及在农业或园艺中控制或预防植物被植物病原微生物，特别是真菌侵染的活性成分或组合物的使用。
• 3-carbonylaminothiophenes and their use as fungicides
  申请人：Syngenta Crop Protection, Inc.

  公开号：US07582589B2

  公开（公告）日：2009-09-01

  The invention also relates to novel compounds of formula (1) where Het is a 5- or 6-membered heterocyclic ring containing one to three heteroatoms, each independently selected from oxygen, nitrogen and sulphur, the ring being substituted by one to three groups R4; R1 is hydrogen, optionally substituted (C1-4)alkyl, formyl, optionally substituted (C1-4)alkylC(═O), optionally substituted (C1-4)alkylC(═O)O, optionally substituted (C1-4)alkoxy(C1-4)alkyl, optionally substituted allyl, optionally substituted propargyl or optionally substituted allenyl; each R2 is, independently, halogen, optionally substituted (C1-4)alkyl, optionally substituted (C1-4)alkoxy or optionally substituted (C1-4)alkoxy(C1-4)alkyl; R3 is either at position 2 or at position 4 of the thiophene ring and is an organic group containing three to thirteen carbon atoms and at least one silicon atom and, optionally, one to three heteroatoms, each independently selected from oxygen, nitrogen and sulphur, and is optionally substituted by one to four independently selected halogen atoms; each R4 is, independently, halogen, C1-3 alkyl, C1-3 haloalkyl, C1-3alkoxy(C1-3)alkyl or cyano; r is 0, 1 or 2; and X is 0 or S; or an N-oxide thereof, to novel intermediates used in the preparation of these compounds, to agrochemical compositions which comprise at least one of the novel compounds as an active ingredient and to the use of the active ingredients or compositions in agriculture or horticulture for controlling or preventing infestation of plants by phytopathogenic microorganisms, preferably fungi.

  该发明涉及式（1）的新化合物，其中Het是一个含有1-3个杂原子的5-或6元杂环，杂原子独立地选自氧、氮和硫，该环被1-3个R4基取代；R1是氢、可选取代（C1-4）烷基、甲酰基、可选取代（C1-4）烷基C（═O）、可选取代（C1-4）烷基C（═O）O、可选取代（C1-4）烷氧（C1-4）烷基、可选取代烯丙基、可选取代丙炔基或可选取代烯基基；每个R2是独立的卤素、可选取代（C1-4）烷基、可选取代（C1-4）烷氧基或可选取代（C1-4）烷氧基（C1-4）烷基；R3位于噻吩环的2或4位置，是一个有机基团，含有3-13个碳原子和至少一个硅原子，还可以选自氧、氮和硫的1-3个杂原子，可以被1-4个独立选择的卤素原子取代；每个R4是独立的卤素、C1-3烷基、C1-3卤代烷基、C1-3烷氧基（C1-3）烷基或氰基；r为0、1或2；X为0或S；或其N-氧化物，以及用于制备这些化合物的新中间体，包括至少一种新化合物作为活性成分的农药组合物，以及在农业或园艺中控制或预防植物受植物病原微生物，特别是真菌侵袭的活性成分或组合物的用途。
• Ligand-Enabled Ni–Al Bimetallic Catalysis for Nonchelated Dual C–H Annulation of Arylformamides and Alkynes
  作者：Yin-Xia Wang、Feng-Ping Zhang、Yu-Xin Luan、Mengchun Ye

  DOI：10.1021/acs.orglett.0c00432

  日期：2020.3.20

  A bifunctional secondary phosphine oxide (SPO) ligand-controlled method was developed for Ni-Al-catalyzed nonchelated dual C-H annulation of arylformamides with alkynes, providing a series of substituted amide-containing heterocycles in <= 97% yield. The SPO-bound bimetallic catalysis proved to be critical to the reaction efficiency.
• PAULMIER C., BULL. SOC. CHIM. FRANCE, 1979, PART 2, NO 11-12, 592-598
  作者：PAULMIER C.

  DOI：——

  日期：——
• OUTURQUIN, F.;LEROUGE, P.;PAULMIER, C., BULL. SOC. CHIM. FR., 1986, N 2, 259-266
  作者：OUTURQUIN, F.、LEROUGE, P.、PAULMIER, C.

  DOI：——

  日期：——