2,3-二甲基-1-苯并噻吩-7-胺 | 570430-12-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻吩类
• 中文名称: 2,3-二甲基-1-苯并噻吩-7-胺
• 英文名称: 7-amino-2,3-dimethylbenzo[b]thiophene
• 英文别名: Benzo[b]thiophen-7-amine, 2,3-dimethyl-；2,3-dimethyl-1-benzothiophen-7-amine
• CAS: 570430-12-5
• 化学式: C₁₀H₁₁NS
• 分子量: 177.27
• InChiKey: QBQVVDGJEFKDDN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  54.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-氨基吡啶 、 2,3-二甲基-1-苯并噻吩-7-胺 在 palladium diacetate caesium carbonate 、 4,5-双二苯基膦-9,9-二甲基氧杂蒽 作用下， 以 1,4-二氧六环 为溶剂， 反应 5.0h， 以76%的产率得到N-(2,3-Dimethyl-1-benzothiophen-7-yl)pyridin-3-amine
  参考文献：
  名称：

  Synthesis and antioxidant activity evaluation of new 7-aryl or 7-heteroarylamino-2,3-dimethylbenzo[b]thiophenes obtained by Buchwald–Hartwig C–N cross-coupling

  摘要：

  New 7-aryl or 7-heteroarylamino-2,3-dimethylbenzo[b]thiophenes were prepared by palladium-catalyzed Buchwald-Hartwig cross-coupling of 7-bromo or 7-amino-2,3-dimethylbenzo[b]thiophenes, previously prepared by us, with substituted (4-methoxy or 3,4-dimethoxy) anilines and 3-aminopyridine or with substituted (3-methoxy or 4-cyano) bromobenzenes and 2-bromopyridine, respectively, using Pd(OAc)(2), rac-BINAP or Xamphos as ligands, and Cs2CO3 as base. Their antioxidant properties were evaluated by several methods: reducing power, scavenging effect on 2,2-diphenyl-1-picrylhydrazyl (DPPH) radicals, inhibition of erythrocyte hemolysis and inhibition of lipid peroxidation using the beta-carotene linoleate system. EC50 values for all the methods were determined and it was possible to establish some structure-activity relationships (SARs) based on the presence and position of different substituents on the phenyl ring (1 or 2 OMe and C equivalent to N), on the presence of a pyridine ring and on the position of its nitrogen atom relative to the N-H bond. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.11.035
• 作为产物：
  描述：

  7-溴-2,3-二甲基-苯并[b]噻吩 在 盐酸 、 palladium diacetate 、 caesium carbonate 、 R-(+)-1,1'-联萘-2,2'-双二苯膦 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 21.0h， 生成 2,3-二甲基-1-苯并噻吩-7-胺
  参考文献：
  名称：

  含有苯并[b]噻吩部分的新型氨基酸和脱氢氨基酸的合成

  摘要：

  通过迈克尔加成或顺序迈克尔加成和钯催化的 C-C 或 CN 交叉偶联制备了几种含有苯并 [b] 噻吩部分的新型氨基酸和脱氢氨基酸。迈克尔加成的底物是 N,N-双(叔丁氧羰基)脱氢丙氨酸 [Boc2-ΔAla-OMe] 和 N-(4-甲苯磺酰基)-N-(叔丁氧羰基)脱氢丙氨酸 [Tos-ΔAla( N-Boc)-OMe]，亲核试剂是芳香族硫醇和 3-碘苄胺。将巯基苯并[b]噻吩直接添加到 Tos-ΔAla(N-Boc)-OMe 中，立体选择性地以良好的产率得到相应脱氢半胱氨酸的 E-异构体。当苯硫酚和 3-碘苄胺用作亲核试剂时，附加官能团（卤素或胺）的存在允许随后钯催化的与官能化苯并[b]噻吩（硼酸、卤素或胺）的交叉偶联反应。使用这种策略，以良好的收率获得了几种外消旋氨基酸和脱氢氨基酸衍生物，它们通过芳族间隔基连接到苯并 [b] 噻吩部分。(© Wiley-VCH Verlag GmbH &

  DOI：

  10.1002/ejoc.200390212

文献信息

• Sonogashira Cross-Couplings of Dehydroamino Acid Derivatives and Phenylacetylenes
  作者：Ana S. Abreu、Paula M. T. Ferreira、Maria-João R. P. Queiroz、Emanuela Gatto、Mariano Venanzi

  DOI：10.1002/ejoc.200400145

  日期：2004.10

  some extent. The Sonogashira products obtained from the 4-bromophenylacetylene were allowed to react with functionalized benzo[b]thiophenes under C−C or C−N palladium-catalyzed cross-coupling conditions. Preliminary fluorescence studies were performed for mono- and disubstituted (4-aminophenyl)acetylenic dehydroamino acids and for the benzo[b]thiophene derivatives. The results showed that some of the

  几种苯乙炔在 Sonogashira 交叉偶联条件下与 N-（叔丁氧基羰基）-（E）-β-溴-或-β，β-二溴脱氢丙氨酸的甲酯偶联，得到β-取代或β，β-二取代脱氢丙氨酸，分别。在通常的 Sonogashira 条件下（1 当量苯乙炔，1 mol% [Pd(PPh3)4]，2 mol% CuI，18 NEt3 在乙腈中的当量，室温下 24 小时），保留立体化学。反过来，在改良的 Sonogashira 条件下（4 当量的苯乙炔，10 mol% 的 [PdCl2(PPh3)2]，20 mol % CuI，1.4 当量 Cs2CO3 乙腈溶液，回流 2 小时）。在后面的反应中，一些苯乙炔二聚体和单取代偶联产物的（E）异构体也得到了一定程度的分离。在 C-C 或 CN 钯催化的交叉偶联条件下，允许从 4-溴苯基乙炔获得的 Sonogashira 产物与功能化的苯并 [b] 噻吩反应。对单和二取代
• Synthesis and antioxidant activity evaluation of new 7-aryl or 7-heteroarylamino-2,3-dimethylbenzo[b]thiophenes obtained by Buchwald–Hartwig C–N cross-coupling
  作者：Maria-João R.P. Queiroz、Isabel C.F.R. Ferreira、Ricardo C. Calhelha、Letícia M. Estevinho

  DOI：10.1016/j.bmc.2006.11.035

  日期：2007.2

  New 7-aryl or 7-heteroarylamino-2,3-dimethylbenzo[b]thiophenes were prepared by palladium-catalyzed Buchwald-Hartwig cross-coupling of 7-bromo or 7-amino-2,3-dimethylbenzo[b]thiophenes, previously prepared by us, with substituted (4-methoxy or 3,4-dimethoxy) anilines and 3-aminopyridine or with substituted (3-methoxy or 4-cyano) bromobenzenes and 2-bromopyridine, respectively, using Pd(OAc)(2), rac-BINAP or Xamphos as ligands, and Cs2CO3 as base. Their antioxidant properties were evaluated by several methods: reducing power, scavenging effect on 2,2-diphenyl-1-picrylhydrazyl (DPPH) radicals, inhibition of erythrocyte hemolysis and inhibition of lipid peroxidation using the beta-carotene linoleate system. EC50 values for all the methods were determined and it was possible to establish some structure-activity relationships (SARs) based on the presence and position of different substituents on the phenyl ring (1 or 2 OMe and C equivalent to N), on the presence of a pyridine ring and on the position of its nitrogen atom relative to the N-H bond. (c) 2006 Elsevier Ltd. All rights reserved.
• Synthesis of Novel Amino Acids and Dehydroamino Acids Containing the Benzo[b]thiophene Moiety
  作者：Ana S. Abreu、Natália O. Silva、Paula M. T. Ferreira、Maria-João R. P. Queiroz

  DOI：10.1002/ejoc.200390212

  日期：2003.4

  Several novel amino acids and dehydroamino acids containing the benzo[b]thiophene moiety were prepared by Michael addition or sequential Michael addition and palladium-catalyzed C−C or C−N cross couplings. The substrates for Michael addition were the methyl esters of N,N-bis(tert-butyloxycarbonyl)dehydroalanine [Boc2−ΔAla−OMe] and N-(4-toluenesulfonyl)-N-(tert-butyloxycarbonyl)dehydroalanine [Tos−ΔAla(N-Boc)−OMe]

  通过迈克尔加成或顺序迈克尔加成和钯催化的 C-C 或 CN 交叉偶联制备了几种含有苯并 [b] 噻吩部分的新型氨基酸和脱氢氨基酸。迈克尔加成的底物是 N,N-双(叔丁氧羰基)脱氢丙氨酸 [Boc2-ΔAla-OMe] 和 N-(4-甲苯磺酰基)-N-(叔丁氧羰基)脱氢丙氨酸 [Tos-ΔAla( N-Boc)-OMe]，亲核试剂是芳香族硫醇和 3-碘苄胺。将巯基苯并[b]噻吩直接添加到 Tos-ΔAla(N-Boc)-OMe 中，立体选择性地以良好的产率得到相应脱氢半胱氨酸的 E-异构体。当苯硫酚和 3-碘苄胺用作亲核试剂时，附加官能团（卤素或胺）的存在允许随后钯催化的与官能化苯并[b]噻吩（硼酸、卤素或胺）的交叉偶联反应。使用这种策略，以良好的收率获得了几种外消旋氨基酸和脱氢氨基酸衍生物，它们通过芳族间隔基连接到苯并 [b] 噻吩部分。(© Wiley-VCH Verlag GmbH &