6-methoxy-N-(4-methoxybenzylidene)benzo[d]thiazol-2-amine | 62724-91-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻唑类
• 英文名称: 6-methoxy-N-(4-methoxybenzylidene)benzo[d]thiazol-2-amine
• 英文别名: (6-methoxy-benzothiazol-2-yl)-(4-methoxy-benzylidene)-amine；N-(6-methoxy-1,3-benzothiazol-2-yl)-1-(4-methoxyphenyl)methanimine
• CAS: 62724-91-8
• 化学式: C₁₆H₁₄N₂O₂S
• 分子量: 298.365
• InChiKey: IJYNFOFJCFTPNR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.06
• 重原子数：
  21.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  43.71
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  苯氧乙酰氯 、 6-methoxy-N-(4-methoxybenzylidene)benzo[d]thiazol-2-amine 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 8.0h， 以74%的产率得到1-(6-methoxybenzo[d]thiazol-2-yl)-4-(4-methoxyphenyl)-3-phenoxyazetidin-2-one
  参考文献：
  名称：

  Synthesis and Characterization of Some 2-Azetidinones and Unexpected Azet-2(1H)-ones

  摘要：

  2-Azetidinone (2b-e) and some unexpected azet-2(1H)-one derivatives (3b-f) were synthesized in two steps from the substitution of 2-aminobenzothiazole and different substituted aromatic aldehydes. Firstly, the Schiff bases were prepared via reaction of different 2-aminobenzothiazoles with different aromatic aldehydes. Second step was the formation of corresponding 2-azetidinone and some unexpected azet-2(1H)-one analogues by cyclocondensation of the Schiff bases with chloroacetyl chloride and phenoxy acetyl chloride in the presence of triethylamine. The chemical structures of the newly synthesized compounds were confirmed by FTIR, H-1 NMR, C-13 NMR, HMQC, elemental analysis and mass spectroscopic analysis.

  DOI：

  10.5562/cca3386
• 作为产物：
  描述：

  2-氨基-6-甲氧基苯并噻唑 、 4-甲氧基苯甲醛 在 硫酸 作用下， 以 甲苯 为溶剂， 反应 48.0h， 以85%的产率得到6-methoxy-N-(4-methoxybenzylidene)benzo[d]thiazol-2-amine
  参考文献：
  名称：

  Synthesis and Characterization of Some 2-Azetidinones and Unexpected Azet-2(1H)-ones

  摘要：

  2-Azetidinone (2b-e) and some unexpected azet-2(1H)-one derivatives (3b-f) were synthesized in two steps from the substitution of 2-aminobenzothiazole and different substituted aromatic aldehydes. Firstly, the Schiff bases were prepared via reaction of different 2-aminobenzothiazoles with different aromatic aldehydes. Second step was the formation of corresponding 2-azetidinone and some unexpected azet-2(1H)-one analogues by cyclocondensation of the Schiff bases with chloroacetyl chloride and phenoxy acetyl chloride in the presence of triethylamine. The chemical structures of the newly synthesized compounds were confirmed by FTIR, H-1 NMR, C-13 NMR, HMQC, elemental analysis and mass spectroscopic analysis.

  DOI：

  10.5562/cca3386

文献信息

• Highly enantioselective Mannich reactions of imines with tert-butyl acetoacetate catalyzed by squaramide organocatalyst
  作者：Hai-Xiao He、Da-Ming Du

  DOI：10.1016/j.tetasy.2014.03.010

  日期：2014.4

  Highly enantioselective Mannich reactions of imines bearing a benzothiazole moiety with tert-butyl acetoacetate, catalyzed by a cinchona-based squaramide organocatalyst have been developed. The corresponding benzothiazole β-keto ester derivatives were obtained in high yields (up to 99%) and with excellent enantioselectivities (up to 98% ee).

  轴承用的苯并噻唑基部分亚胺的对映选择性高度曼尼希反应叔丁基乙酰乙酸酯，由基于金鸡纳-squaramide有机催化剂催化的已被开发。获得了相应的苯并噻唑β-酮酯衍生物，收率高（高达99％），对映选择性极好（ee高达98％）。
• Chiral phosphoric acid-catalyzed enantioselective construction of structurally diverse benzothiazolopyrimidines
  作者：Lucie Jarrige、Danijel Glavač、Guillaume Levitre、Pascal Retailleau、Guillaume Bernadat、Luc Neuville、Géraldine Masson

  DOI：10.1039/c8sc05581e

  日期：——

  A highly efficient catalytic enantioselective [4+2] cycloaddition was developed between 2-benzothiazolimines and enecarbamates. A wide range of benzothiazolopyrimidines bearing three contiguous stereogenic centers was obtained in high to excellent yields and with excellent diastereo- and enantioselectivities (d.r. > 98 : 2 and up to >99% ee). Furthermore, this chiral phosphoric acid-catalyzed strategy

  在2-苯并噻唑亚胺和烯氨基甲酸酯之间开发了一种高效催化对映选择性[4+2]环加成反应。以高至优异的收率获得了多种带有三个连续立体中心的苯并噻唑并嘧啶，并具有优异的非对映和对映选择性（dr > 98 : 2 和高达 > 99% ee）。此外，这种手性磷酸催化策略具有可扩展性，并且能够获得一类新型光学纯路易斯碱异硫脲衍生物。
• Organocatalytic Enantioselective Strecker Reaction of Imines Containing a Thiazole Moiety by Using a Cinchona-Based Squaramide Catalyst
  作者：Hai-Xiao He、Da-Ming Du

  DOI：10.1002/ejoc.201402764

  日期：2014.10

  organocatalytic enantioselective Strecker reaction was developed for the synthesis of α-amino nitriles that contain a thiazole moiety by using a cinchona-based squaramide catalyst. The corresponding products were obtained in good to excellent yields (up to 99 %) with excellent enantioselectivities (up to 98 % ee) by starting from aromatic-substituted imines. In addition, two trifunctional squaramides

  开发了一种有机催化对映选择性 Strecker 反应，用于通过使用基于金鸡纳的方酸酰胺催化剂合成含有噻唑部分的 α-氨基腈。通过从芳族取代的亚胺开始，以良好到极好的产率（高达 99%）和极好的对映选择性（高达 98% ee）获得了相应的产品。此外，合成了两种具有氨基酸残基的三官能方酸酰胺，当它们用于模型反应时，实现了良好的对映选择性（高达 89% ee）。
• Benzothiazole Schiff-bases as potential imaging agents for β-amyloid plaques in Alzheimer’s disease
  作者：Changsheng Gan、Lin Zhou、Zhenzhen Zhao、Haoshu Wang

  DOI：10.1007/s00044-012-0416-0

  日期：2013.9

  A series of benzothiazole Schiff-bases as potential diagnostic imaging agents targeting beta-amyloid (A beta) plaques in Alzheimer's disease (AD) were synthesized and evaluated. When in vitro binding studies using AD homogenate with [I-125] 6-iodo-2-(4'-dimethyl- amino)-phenyl-imidazo[1,2-alpha]pyridine ([I-125]IMPY) as the reference ligand were carried out with the derivatives, the compounds showed high to low binding affinities for AD homogenate at the K (i) values ranged from 4.38 to 514.65 nM, depending on the substitution on the phenyl ring. Fluorescent staining in vitro showed that one compound with a N,N-dimethylamino group intensely stained A beta plaques within brain sections of postmortem AD patients. The results strongly suggest that these derivatives are worthy of further study and may be a useful amyloid imaging agents for early detection of amyloid plaques in the brain of AD.
• Synthesis and Characterization of Some 2-Azetidinones and Unexpected Azet-2(1H)-ones
  作者：Handan Can Sakarya、Merve Yandımoğlu

  DOI：10.5562/cca3386

  日期：——

  2-Azetidinone (2b-e) and some unexpected azet-2(1H)-one derivatives (3b-f) were synthesized in two steps from the substitution of 2-aminobenzothiazole and different substituted aromatic aldehydes. Firstly, the Schiff bases were prepared via reaction of different 2-aminobenzothiazoles with different aromatic aldehydes. Second step was the formation of corresponding 2-azetidinone and some unexpected azet-2(1H)-one analogues by cyclocondensation of the Schiff bases with chloroacetyl chloride and phenoxy acetyl chloride in the presence of triethylamine. The chemical structures of the newly synthesized compounds were confirmed by FTIR, H-1 NMR, C-13 NMR, HMQC, elemental analysis and mass spectroscopic analysis.