2-amino-4-n-butyl-thiazole | 53181-04-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-amino-4-n-butyl-thiazole
• 英文别名: 4-butyl-thiazol-2-ylamine；4-Butyl-thiazol-2-ylamin；2-Amino-4-butyl-thiazol；2-Amino-4-butylthiazol；4-Butyl-1,3-thiazol-2-amine
• CAS: 53181-04-7
• 化学式: C₇H₁₂N₂S
• 分子量: 156.252
• InChiKey: CMDRVSNHYRLGBQ-UHFFFAOYSA-N

物化性质

• 沸点：
  270.8±9.0 °C(Predicted)
• 密度：
  1.114±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  10
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  67.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-amino-4-n-butyl-thiazole 在 ammonium hydroxide 、 硫酸 、 硝酸 作用下， 反应 5.25h， 生成 (E)-N-(6-butyl-2H-thiazolo[3,2-b][1,2,4]thiadiazol-2-ylidene)nitramide
  参考文献：
  名称：

  Products of the nitration of 2-thiazolylureas and 2-thiazolylthioureas.

  摘要：

  报道了2-噻唑基脲和2-噻唑基硫脲衍生物在浓硫酸中与发烟硝酸的硝化产物。研究的脲衍生物为3-(4-甲基-2-噻唑基)脲和硫脲(7)及其1-甲基(分别为1和2)和1,1-二甲基类似物。产物是噻唑部分的5-位发生硝化的化合物。当硝酸过量时，从1得到1-甲基-3-(4-甲基-5-硝基-2-噻唑基)-1-硝基脲，而从2得到相应的1-亚硝基脲。硝化7得到一种淡黄色化合物。与其他硝化硫脲不同，它不形成有色Cu(II)螯合物，且对酸、碱和热稳定。根据其物理化学性质、化学反应和X射线晶体学结果，推断为6-甲基-2-硝亚氨基噻唑并[3,2-b][1,2,4]噻二唑。从其他N-(4-烷基-2-噻唑基)硫脲也得到了相应的化合物。

  DOI：

  10.1248/cpb.32.3483
• 作为产物：
  描述：

  正戊酰溴 在 乙醚 作用下， 生成 2-amino-4-n-butyl-thiazole
  参考文献：
  名称：

  537.消除反应。第一部分：酸催化的酮的烯化和取代反应

  摘要：

  DOI：

  10.1039/jr9510002430

文献信息

• NOVEL GLUCOKINASE ACTIVATORS AND METHODS OF USING SAME
  申请人：Ryono Denis E.

  公开号：US20080009465A1

  公开（公告）日：2008-01-10

  Compounds are provided which are phosphonate and phosphinate activators and thus are useful in treating diabetes and related diseases and have the structure wherein is a heteroaryl ring; R 4 is —(CH 2 ) n -Z-(CH 2 ) m —PO(OR 7 )(OR 8 ), —(CH 2 ) n Z-(CH 2 ) m —PO(OR 7 )R g , —(CH 2 ) n -Z-(CH 2 ) m —OPO(OR 7 )R g , —(CH 2 ) n Z—(CH 2 ) m —OPO(R 9 )(R 10 ), or —(CH 2 ) n Z—(CH 2 ) m —PO(R 9 )(R 10 ); R 5 and R 6 are independently selected from H, alkyl and halogen; Y is R 7 (CH 2 ) s or is absent; and X, n, Z, m, R 4 , R 5 , R 6 , R 7 , and s are as defined herein; or a pharmaceutically acceptable salt thereof. A method for treating diabetes and related diseases employing the above compounds is also provided.

  提供了磷酸酯和磷酸酯激活剂，因此在治疗糖尿病和相关疾病方面非常有用，并具有以下结构： 其中 是杂环芳基环； R 4 为—(CH 2 ) n -Z-(CH 2 ) m —PO(OR 7 )(OR 8 )、—(CH 2 ) n Z-(CH 2 ) m —PO(OR 7 )R g 、—(CH 2 ) n -Z-(CH 2 ) m —OPO(OR 7 )R g 、—(CH 2 ) n Z—(CH 2 ) m —OPO(R 9 )(R 10) 或—(CH 2 ) n Z—(CH 2 ) m —PO(R 9 )(R 10) ； R 5 和R 6 分别选择自H、烷基和卤素； Y为R 7 (CH 2 ) s 或不存在；以及 X、n、Z、m、R 4 、R 5 、R 6 、R 7 和s如本文所定义；或其药用盐。 还提供了一种利用上述化合物治疗糖尿病和相关疾病的方法。
• Studies on Acetylenic Compounds. XXII. Ring Closure. (4). New Synthesis of Thiazoles and Imidazole.
  作者：Yasuo Yura

  DOI：10.1248/cpb.10.376

  日期：——

  It was found that the compounds having the general formula RCH(X)-C≡C-R'gave thiazole derivatives by reaction with thiourea. The relationship between the structure of thiazoles and substituent groups was clarified as follows : (1) When R=R'=Ph, 2-amino-4-benzyl-5-phenylthiazole (IId) is obtained, (2) When R=alkyl, R'=H, two kinds of thiazoles are obtained ; and (3) when R=R'=alkyl, thiazole derivative is not obtained. Similarly, propargyl bromide and phenylpropargyl bromide, when reacted with ammonium dithiocarbamate, afforded 2-mercapto-4-methylthiazole (XX) and 2-mercapto-4-benzylthiazole (XXIII), respectively. Further, 2-amino-4-methylimidazole (XXV) was obtained from guanidine and propargyl bromide.

  研究发现，具有通式RCH(X)-C≡C-R'的化合物在反应中与硫脲作用生成噻唑衍生物。噻唑结构和取代基之间的关系阐明如下：(1) 当R=R'=Ph时，获得2-氨基-4-苄基-5-苯基噻唑(IId)；(2) 当R=烷基，R'=H时，获得两种噻唑；(3) 当R=R'=烷基时，不生成噻唑衍生物。同样地，炔丙基溴和苯基炔丙基溴与氨荒酸盐反应，分别得到2-巯基-4-甲基噻唑(XX)和2-巯基-4-苄基噻唑(XXIII)。进一步地，从胍和炔丙基溴获得2-氨基-4-甲基咪唑(XXV)。
• INHIBITION OF BACTERIAL BIOFILMS WITH IMIDAZOLE DERIVATIVES
  申请人：Melander Christian

  公开号：US20080181923A1

  公开（公告）日：2008-07-31

  Disclosure is provided for imidazole derivative compounds that prevent, remove and/or inhibit the formation of biofilms, compositions comprising these compounds, devices comprising these compounds, and methods of using the same.

  提供了关于咪唑衍生物化合物的披露，这些化合物可以预防、去除和/或抑制生物膜的形成，包括这些化合物的组合物、包含这些化合物的设备，以及使用它们的方法。
• INHIBITION OF BIOFILMS IN PLANTS WITH IMIDAZOLE DERIVATIVES
  申请人：Melander Christian

  公开号：US20090143230A1

  公开（公告）日：2009-06-04

  Disclosure is provided for methods of preventing, removing or inhibiting microbial biofilm formation or microbial infection in a plant or plant part thereof, including applying thereto a treatment effective amount of an active compound as described herein, or an agriculturally acceptable salt thereof. Methods of enhancing a microbicide (e.g., including a copper, antibiotic, bacteriophage, etc.) and/or plant defense activator are also provided, including applying an active compound as described herein. Compositions comprising an active compound as described herein in an agriculturally acceptable carrier are also provided, and in some embodiments the compositions further include a microbicide (e.g., including copper, antibiotic, bacteriophage, etc.) and/or plant defense activator.

  本公开提供了一种防止、去除或抑制植物或其部分中微生物生物膜形成或微生物感染的方法，包括向其施加本文所述的活性化合物的有效量或其农业可接受的盐。还提供了增强微生物杀灭剂（例如，包括铜、抗生素、噬菌体等）和/或植物防御激活剂的方法，包括施加本文所述的活性化合物。还提供了包含本文所述的活性化合物在农业可接受载体中的组合物，并在某些实施例中，这些组合物进一步包括微生物杀灭剂（例如，包括铜、抗生素、噬菌体等）和/或植物防御激活剂。
• Facile Preparation of Thiazoles from 1<i>H</i>-1-(1′-Alkynyl)-5-methyl-1,2,3-benziodoxathiole 3,3-Dioxide with Thioamides
  作者：Hideo Togo、Yoshihide Ishiwata

  DOI：10.1055/s-0028-1083439

  日期：——

  Thiazoles were obtained in high yields by the reaction of 1H-1-(1′-alkynyl)-5-methyl-1,2,3-benziodoxathiole 3,3-dioxides, which were easily prepared from the reaction of 1H-1-hydroxy-5-methyl-1,2,3-benziodoxathiole 3,3-dioxide and 1-alkynes, with thioamides. Here, the co-product, potassium 2-iodo-5-methylbenzenesulfonate, was recovered quantitatively by simple filtration of the reaction mixture, and was regenerated to 1H-1-(1′-alkynyl)-5-methyl-1,2,3-benziodoxathiole 3,3-dioxides to be reused for the same preparation of thiazoles, keeping good yields.

  通过1H-1-(1′-炔基)-5-甲基-1,2,3-苯并碘氧硫杂环戊烷3,3-二氧化物与硫酰胺的反应，可以高产率地获得噻唑类化合物。这些1H-1-(1′-炔基)-5-甲基-1,2,3-苯并碘氧硫杂环戊烷3,3-二氧化物很容易通过1H-1-羟基-5-甲基-1,2,3-苯并碘氧硫杂环戊烷3,3-二氧化物与1-炔的反应制备得到。在此过程中，副产物——2-碘-5-甲基苯磺酸钾——通过简单过滤反应混合物即可定量回收，并可再生为1H-1-(1′-炔基)-5-甲基-1,2,3-苯并碘氧硫杂环戊烷3,3-二氧化物，再次用于相同噻唑的制备，保持良好的产率。