tert-Butyl (4-amino-3-thienyl)carbamate | 194350-10-2

• 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: tert-Butyl (4-amino-3-thienyl)carbamate
• 英文别名: t-butyl (4-aminothien-3-yl)carbamate；3-amino-4-t-butoxycarbonylaminothiophene；tert-butyl N-(4-aminothiophen-3-yl)carbamate
• CAS: 194350-10-2
• 化学式: C₉H₁₄N₂O₂S
• 分子量: 214.288
• InChiKey: JIAMDKAPNVGERK-UHFFFAOYSA-N

物化性质

• 沸点：
  309.2±27.0 °C(Predicted)
• 密度：
  1.258±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  92.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  tert-Butyl (4-amino-3-thienyl)carbamate 在 溶剂黄146 作用下， 反应 1.0h， 以89%的产率得到di-t-butyl (amino-3,4-thienylidene)dicarbamate
  参考文献：
  名称：

  （4-氨基噻吩-3-基）氨基甲酸酯烷基酯的合成与反应性

  摘要：

  由3，4-二氨基噻吩1制备单氨基甲酸酯2，并在酸催化下使用醛和硒酚在噻吩核上烷基化。该反应已经允许访问2-烷基-3,4- diaminothiophenes 9，3,5- diaminodithieno并[3,2-B：2'，3'-E]吡啶10和1-烷基噻吩并[3,4-d ]咪唑酮13。

  DOI：

  10.1016/s0040-4020(97)00681-9
• 作为产物：
  描述：

  二碳酸二叔丁酯 、 3,4-diaminothiophene dihydrochloride 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 以58%的产率得到tert-Butyl (4-amino-3-thienyl)carbamate
  参考文献：
  名称：

  NOVEL THIOPHENEDIAMINE DERIVATIVE HAVING UREA STRUCTURE

  摘要：

  公开号：

  EP2292611B1

文献信息

• Studies on the reactivity of N-(3-thienyl)carbamates
  作者：Delphine Brugier、Francis Outurquin、Claude Paulmier

  DOI：10.1039/b003580g

  日期：——

  tert-Butyl 2-allyl- and N-allyl-3-thienylcarbamates were used as substrates for the preparation of thieno[3,2-b]pyrroles 9 and 5,6-dihydrothieno[3,2-b]pyrroles 10. Pd-catalyzed cyclization of N-allyl-(2-bromo-3-thienyl)carbamates 12 has allowed access to thienopyrroles 9. The radical route has led to the formation of a dihydrothienopyrrole 10 or a tetrahydrothienopyridine 19 according to the β-substitution of the allyl substituent. The nucleophilic participation of the tert-butoxycarbonyl group occurred during the selenium or iodine-induced cyclization of tert-butyl 2-allyl- or N-allyl-3-thienylcarbamates. The formation of the thienooxazepinone 25 and N-(3-thienyl)oxazolidinones 28 and 29 was observed.

  叔丁基2-烯丙基和N-烯丙基-3-噻吩基氨基甲酸酯被用作底物，以制备噻吩[3,2-b]吡咯9和5,6-二氢噻吩[3,2-b]吡咯10。钯催化的环化反应中，N-烯丙基-(2-溴-3-噻吩基)氨基甲酸酯12使得噻吩吡咯9的合成成为可能。自由基途径则根据烯丙基取代基的β-取代，引导形成二氢噻吩吡咯10或四氢噻吩吡啶19。叔丁氧羰基基团在硒或碘诱导的叔丁基2-烯丙基或N-烯丙基-3-噻吩基氨基甲酸酯的环化过程中发生了亲核参与。观察到了噻吩并噁唑啉酮25和N-(3-噻吩基)噁唑烷酮28和29的形成。
• α-Substitution of β-Thienylcarbamates: Alkylation, Vinylation and Pd-Catalyzed Coupling Reactions
  作者：Delphine Brugier、Francis Outurquin、Claude Paulmier

  DOI：10.1016/s0040-4020(00)00173-3

  日期：2000.5

  Acid catalyzed α-alkylation of 4, using α-branched or functionalized aldehydes, has allowed the synthesis of divinylthiophenes 13 and thieno[3,2–b]pyridines 14–16, respectively. Pd-catalyzed coupling reactions involving halo- or dihalothienylcarbamates 10, 17, 18 were studied. One or two alkenyl, alkynyl, aryl groups were introduced on the thiophene nucleus.

  的trilithio衍生物的反应二-吨-丁基噻吩-3,4- diyldicarbamate 4与烷基卤化物已经导致2- alkylthiophenedicarbamates 9和11和4- alkylthieno [3,4-d]咪唑酮12。酸催化的α-烷基化4，使用α-支化或官能化的醛，已经允许divinylthiophenes的合成13和噻吩并[3,2-B]吡啶14 - 16，分别。Pd催化的偶联涉及卤代反应或dihalothienylcarbamates 10，17，18被研究了。在噻吩核上引入一个或两个烯基，炔基，芳基。
• Thiophenediamine derivative having urea structure
  申请人：Santen Pharmaceutical Co., Ltd.

  公开号：US08288380B2

  公开（公告）日：2012-10-16

  A compound of formula (1): wherein R1 and R2 represent hydrogen, lower alkyl, lower alkenyl, lower alkynyl or R3 represents hydroxyl, lower alkoxy, lower cycloalkyloxy, aryloxy, carboxy, lower alkoxycarbonyl, or NRaRb of the formula R4 and R5 represent halogen, lower alkyl, hydroxyl, or lower alkoxy; R6 represents halogen, lower alkyl, aryl, heterocyclic, hydroxy, lower alkoxy, mercapto, lower alkylthio, lower alkylcarbonyl, amino, nitro or cyano; R7 represents lower alkyl, hydroxyl or lower alkoxy; Ra and Rb represent hydrogen or lower alkyl; ring A represents a cyclic hydrocarbon or a heterocyclic ring; ring B represents a heterocyclic ring; X represents lower alkylene; Z represents a single bond or lower alkylene; Y represents lower alkylene and W1—W2 represents CH—CH, or Y represents a single bond and W1—W2 represents N—CH, CH—N or CH—CH; and 1, m, n and o represent 0, 1, 2, or 3.

  化合物的式子（1）：其中，R1和R2代表氢、低碳基、低烯基、低炔基或R3代表羟基、低烷氧基、低环烷氧基、芳氧基、羧基、低烷氧羰基或公式NRaRb的氮代基；R4和R5代表卤素、低碳基、羟基或低烷氧基；R6代表卤素、低碳基、芳基、杂环基、羟基、低烷氧基、硫巴、低烷硫基、低烷基氧羰基、氨基、硝基或氰基；R7代表低碳基、羟基或低烷氧基；Ra和Rb代表氢或低碳基；环A代表环烃或杂环；环B代表杂环；X代表低碳基亚烷基；Z代表单键或低碳基亚烷基；Y代表低碳基亚烷基，W1—W2代表CH—CH，或Y代表单键，W1—W2代表N—CH、CH—N或CH—CH；1、m、n和o代表0、1、2或3。
• 8-Propyldithieno[3,2-<i>b</i>:2′,3′-<i>e</i>]pyridine-3,5-diamine (DITIPIRAM) Derivatives as Neutral Receptors Tailored for Binding of Carboxylates
  作者：Agnieszka Cholewiak、Agnieszka Tycz、Janusz Jurczak

  DOI：10.1021/acs.orglett.7b01235

  日期：2017.6.2

  The DITIPIRAM (8-propyldithieno[3,2-b:2',3'-e]pyridine-3,5-diamine)-based receptors 11 and 12 were readily synthesized, and their anion-binding properties were studied both in solution and in the solid-state. 1H NMR titrations revealed that receptor 12 equipped with two phenyl-urea groups preferentially binds carboxylates, even in the highly competitive DMSO-d6/CD3OH solvent mixture. X-ray analysis showed that receptor 12 exhibited great complementarity for benzoate, which is cooperatively bound by the means of four highly directional hydrogen bonds from the two urea groups. Comparison with the most effective acyclic receptors based on a structurally related rigid carbazole platform demonstrates that the DITIPIRAM motif provides a better suited geometry in the binding pocket, and consequently stronger anion binding.
• US8198271B2
  申请人：——

  公开号：US8198271B2

  公开（公告）日：2012-06-12