methyl 3-isocyanato-2-thiophenecarboxylate | 25712-16-7

• 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: methyl 3-isocyanato-2-thiophenecarboxylate
• 英文别名: Methyl 3-isocyanatothiophene-2-carboxylate
• CAS: 25712-16-7
• 化学式: C₇H₅NO₃S
• mdl: MFCD09971934
• 分子量: 183.188
• InChiKey: SKYDNLJVNFYBGY-UHFFFAOYSA-N

物化性质

• 熔点：
  54-56 °C
• 沸点：
  105-110 °C(Press: 3 Torr)
• 密度：
  1.34±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.142
• 拓扑面积：
  84
• 氢给体数：
  0
• 氢受体数：
  5

安全信息

• 海关编码：
  2934999090

反应信息

• 作为反应物：
  描述：

  methyl 3-isocyanato-2-thiophenecarboxylate 、 Propan-2-yl 2-amino-4,5,6,7,8,9-hexahydrocycloocta[b]thiophene-3-carboxylate 在 吡啶 作用下， 反应 18.0h， 以21%的产率得到
  参考文献：
  名称：

  A new class of small molecule RNA polymerase inhibitors with activity against Rifampicin-resistant Staphylococcus aureus1

  摘要：

  The RNA polymerase holoenzyme is a proven target for antibacterial agents. A high-throughput screening program based on this enzyme from Staphylococcus aureus had previously identified a 2-ureidothiophene-3-carboxylate as a low micromolar inhibitor. An investigation of the relationships between the structures of this class of compounds and their inhibitory- and antibacterial activities is described here, leading to a set of potent RNA polymerase inhibitors with antibacterial activity. Characterization of this bioactivity, including studies of the mechanism of action, is provided, highlighting the power of the reverse chemical genetics approach in providing tools to inhibit the bacterial RNA polymerase. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.05.035
• 作为产物：
  描述：

  3-氨基-2-噻吩甲酸甲酯 在 三乙胺 作用下， 以 甲苯 为溶剂， 反应 2.0h， 生成 methyl 3-isocyanato-2-thiophenecarboxylate
  参考文献：
  名称：

  Organosilicon synthesis of isocyanates: I. Synthesis of isocyanates of the furan, thiophene, and mono-and polyfluorophenyl series

  摘要：

  A convenient synthesis of known and unknown isocyanates of the furan, thiophene, and mono- and polyfluorophenyl series, involving silylation of starting amines with hexamethyldisilazane or chlorotrimethylsilane, followed by phosgenation of the resulting N-silyl-substituted amines. An unusual high-temperature rearrangement of 3-(methoxycarbonyl)-4,5-dimethylthiophene-2-yl isocyanate into its 5-ethyl isomer. ortho-Fluorine substituent in anilines decreases the yield of isocyanates, whereas 2,3,5,6-tetrafluorophenyl isocyanate exists for only a short time as a 5% toluene solution.

  DOI：

  10.1134/s1070363206010208

文献信息

• Heterocyclic dihydrazole compounds and their use for controlling fungal
  申请人：E. I. du Pont de Nemours and Company

  公开号：US06096895A1

  公开（公告）日：2000-08-01

  Compounds of Formula I, and their N-oxides and agriculturally suitable salts, are disclosed which are useful as fungicides ##STR1## In said formula, E is a ring system selected from certain 5- to 12-membered monocyclic and fused bicyclic aromatic heterocyclic ring systems, or an optionally substituted naphthalene ring as defined in the disclosure; A is O; S; N; NR.sup.5 ; or CR.sup.14 ; G is C or N; provided that when G is C, then A is O, S or NR.sup.5 and the floating double bond is attached to G; and when G is N, then A is N or CR.sup.14 and the floating double bond is attached to A; W is O; S; NH; N(C.sub.1 -C.sub.6 alkyl); or NO(C.sub.1 -C.sub.6 alkyl); X is OR.sup.1 ; S(O).sub.m R.sup.1 ; or halogen; R.sup.1 is C.sub.1 -C.sub.6 alkyl; C.sub.1 -C.sub.6 haloalkyl; C.sub.2 -C.sub.6 alkenyl; C.sub.2 -C.sub.6 haloalkenyl; C.sub.2 -C.sub.6 alkynyl; C.sub.2 -C.sub.6 haloalkynyl; C.sub.3 -C.sub.6 cycloalkyl; C.sub.2 -C.sub.4 alkylcarbonyl; or C.sub.2 -C.sub.4 alkoxycarbonyl; R.sup.2 is H; C.sub.1 -C.sub.6 alkyl; C.sub.1 -C.sub.6 haloalkyl; C.sub.2 -C.sub.6 alkenyl; C.sub.2 -C.sub.6 haloalkenyl; C.sub.2 -C.sub.6 alkynyl; C.sub.2 -C.sub.6 haloalkynyl; C.sub.3 -C.sub.6 cycloalkyl; C.sub.2 -C.sub.4 alkylcarbonyl; C.sub.2 -C.sub.4 alkoxycarbonyl; hydroxy; C.sub.1 -C.sub.2 alkoxy; or acetyloxy; R.sup.5 is H; C.sub.1 -C.sub.6 alkyl; C.sub.1 -C.sub.6 haloalkyl; C.sub.2 -C.sub.6 alkenyl; C.sub.2 -C.sub.6 haloalkenyl; C.sub.2 -C.sub.6 alkynyl; C.sub.2 -C.sub.6 haloalkynyl; C.sub.3 -C.sub.6 cycloalkyl; C.sub.2 -C.sub.4 alkylcarbonyl; or C.sub.2 -C.sub.4 alkoxycarbonyl; and Y, Z, R.sup.14 and m are as defined in the disclosure. Also disclosed are compositions containing the compounds of Formula I and a method for controlling plant diseases caused by fungal plant pathogens which involves applying an effective amount of a compound of Formula I.

  公式I的化合物及其N-氧化物和农业适用的盐被披露，可用作杀菌剂。在上述公式中，E是从某些5-至12-成员单环和融合的双环芳香杂环环系统中选择的环系统，或者是如披露中定义的可选择取代的萘环；A是O；S；N；NR^5；或CR^14；G是C或N；但要求当G为C时，A为O、S或NR^5且浮动双键连接到G；当G为N时，A为N或CR^14且浮动双键连接到A；W是O；S；NH；N(C_1-C_6烷基)；或NO(C_1-C_6烷基)；X是OR^1；S(O)_mR^1；或卤素；R^1是C_1-C_6烷基；C_1-C_6卤代烷基；C_2-C_6烯基；C_2-C_6卤代烯基；C_2-C_6炔基；C_2-C_6卤代炔基；C_3-C_6环烷基；C_2-C_4烷基羰基；或C_2-C_4烷氧羰基；R^2是H；C_1-C_6烷基；C_1-C_6卤代烷基；C_2-C_6烯基；C_2-C_6卤代烯基；C_2-C_6炔基；C_2-C_6卤代炔基；C_3-C_6环烷基；C_2-C_4烷基羰基；C_2-C_4烷氧羰基；羟基；C_1-C_2烷氧基；或乙酰氧基；R^5是H；C_1-C_6烷基；C_1-C_6卤代烷基；C_2-C_6烯基；C_2-C_6卤代烯基；C_2-C_6炔基；C_2-C_6卤代炔基；C_3-C_6环烷基；C_2-C_4烷基羰基；或C_2-C_4烷氧羰基；Y、Z、R^14和m如披露中所定义。还披露了含有公式I化合物的组合物以及一种用于控制由真菌植物病原体引起的植物疾病的方法，该方法涉及施用公式I的化合物的有效量。
• Leistungsfördernde Mittel
  申请人：BAYER AG

  公开号：EP0202538A1

  公开（公告）日：1986-11-26

  Die vorliegende Erfindung betrifft leistungsfördernde Mittel für Tiere, die durch einen Gehalt an Thienylharnstoffen oder -isoharnstoffen der formel I in welcher A für die Reste la und Ib steht R3 für die Reste CN, COOR7, CONR8R9, COR10 steht, gekennzeichnet sind.

  本发明涉及用于提高动物性能的组合物，其特征是含有式 I 的噻吩基脲或异脲类化合物。 其中 A 代表基团 la 和 Ib R3 代表自由基 CN、COOR7、CONR8R9、COR10。
• N-(2-Amino-phenyl)-4-(heteroarylmethyl)-benzamides as new histone deacetylase inhibitors
  作者：Arkadii Vaisburg、Isabelle Paquin、Naomy Bernstein、Sylvie Frechette、Frederic Gaudette、Silvana Leit、Oscar Moradei、Stephane Raeppel、Nancy Zhou、Giliane Bouchain、Soon Hyung Woo、Zhiyun Jin、Jeff Gillespie、James Wang、Marielle Fournel、Pu Theresa Yan、Marie-Claude Trachy-Bourget、Marie-France Robert、Aihua Lu、Jimmy Yuk、Jubrail Rahil、A. Robert MacLeod、Jeffrey M. Besterman、Zuomei Li、Daniel Delorme

  DOI：10.1016/j.bmcl.2007.10.050

  日期：2007.12

  A variety of N-(2-amino-phenyl)-4-(heteroarylmethyl)-benzamides were designed and synthesized. These compounds were shown to inhibit recombinant human HDAC I with IC50 values in the sub-micromolar range. In human cancer cells growing in culture these compounds induced hyperacetylation of histones, induced the expression of the tumor suppressor protein p21(WAF1/Cip1), and inhibited cellular proliferation. Certain compounds of this class also showed in vivo activity in various human tumor xenograft models in mice. (c) 2007 Elsevier Ltd. All rights reserved.
• FUNGICIDAL CYCLIC AMIDES
  申请人：E.I. DU PONT DE NEMOURS AND COMPANY

  公开号：EP0825992A1

  公开（公告）日：1998-03-04
• US3940246A
  申请人：——

  公开号：US3940246A

  公开（公告）日：1976-02-24