6-methoxy-N-(4-nitrobenzylidene)benzo[d]thiazol-2-amine | 16779-15-0

• 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-nitrobenzylidene)benzo[d]thiazol-2-amine
• 英文别名: N-(6-methoxy-1,3-benzothiazol-2-yl)-1-(4-nitrophenyl)methanimine
• CAS: 16779-15-0
• 化学式: C₁₅H₁₁N₃O₃S
• 分子量: 313.337
• InChiKey: IECILIDMVAQLCG-UHFFFAOYSA-N

物化性质

• 熔点：
  250-253 °C
• 沸点：
  508.7±56.0 °C(Predicted)
• 密度：
  1.40±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  109
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  6-methoxy-N-(4-nitrobenzylidene)benzo[d]thiazol-2-amine 、 苯氧乙酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 8.0h， 以41%的产率得到1-(6-methoxybenzo[d]thiazol-2-yl)-4-(4-nitrophenyl)-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：

  1-Methoxy-3-rhodan-4-amino-benzol 在 溴 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 12.5h， 生成 6-methoxy-N-(4-nitrobenzylidene)benzo[d]thiazol-2-amine
  参考文献：
  名称：

  设计，合成，表征和对某些细菌菌株的6-甲氧基-2-氨基苯甲硫酸酯衍生物的生物学评估。

  摘要：

  当前的工作报告了对6-甲氧基-2-氨基苯并噻唑（A1）的合成和生物学评估，该合成是通过对氨基苯甲酸与硫氰酸铵反应，然后将所得硫脲与催化量的溴进行氧化闭环而制得的，在碱性介质中。所得化合物（A1）与各种醛进行缩合反应，生成Hy（A3a-d）。在浓HCl和乙二醇溶液存在下，通过化合物（A1）与99.9％水合肼的反应，制得6-甲氧基2-肼基苯并噻唑（A2）。之后，使化合物（A2）与乙酰乙酸乙酯在醇中反应，得到相应的吡唑-6-甲氧基苯并噻唑（A4）。而且，使化合物（A2）与4-取代的芳族醛在无水乙醇中反应，生成Hy（A5a-d）。研究了合成的化合物对五种微生物的抗菌活性：（革兰氏阳性：枯草芽孢杆菌和金黄色葡萄球菌）。（革兰氏阴性：铜绿假单胞菌和肠杆菌）

  DOI：

  10.21608/ejchem.2020.24849.2474

文献信息

• Preparation and Characterization of some new Benzothiazole-Heterocyclic Derivatives
  作者：Radhiya Aldujaili、Ahmed Alhasan

  DOI：10.21608/ejchem.2021.73818.3650

  日期：2021.6.1

  In this work new different hetero cyclic derivatives were synthesized that which including β-Lactam, teterazole and also thiazole rings.The starting material is 2-amino-6-methoxy-Benzothiazole. All these reactions follow by (TLC) and Measurement melting points for some of these derivatives. The compounds identified by FT-IR and some of them by 1H-NMR and 13C-NMR spectra., The prepared benzothiazole derivatives in this study gave good results through appearance of new bands and disapearance of other bands in formatted compounds that gave first data to formation benzothiazole derivative , while second technique represented by resonance spectra that gave also good results for formatted benzothiazole derivative.m in addition to flowing of all reactions by paper chromatography.

  这项工作合成了新的不同杂环衍生物，其中包括 β-内酰胺、特拉唑和噻唑环。所有这些反应都是通过（TLC）和测量其中一些衍生物的熔点进行的。本研究中制备的苯并噻唑衍生物通过在格式化的化合物中出现新的条带和其他条带的消失获得了良好的结果，这为苯并噻唑衍生物的形成提供了第一手数据，而以共振光谱为代表的第二项技术也为格式化的苯并噻唑衍生物提供了良好的结果。
• Chiral Phosphoric Acid‐Catalyzed Enantioselective Formal [4+2] Cycloaddition Between Dienecarbamates and 2‐Benzothioazolimines
  作者：Wei‐Yang Ma、Emeric Montinho‐Inacio、Bogdan I. Iorga、Pascal Retailleau、Xavier Moreau、Luc Neuville、Géraldine Masson

  DOI：10.1002/adsc.202200161

  日期：2022.5.17

  cycloaddition between 2-benzothiazolimines and N-H-1,3-dienecarbamates is described. A divergence in reaction pathways was observed depending on the dienes employed. The reaction performed with 4-substituted dienes produced benzothiazolopyrimidines as major product in yields ranging from 42 to 67%, as single diastereoisomer and with enantioselectivity between 93 and 99%. The same reaction performed with

  描述了 2-苯并噻唑亚胺和N -H-1,3-二烯氨基甲酸酯之间的对映选择性手性磷酸催化的形式 [4+2] 环加成。根据所使用的二烯，观察到反应途径的分歧。用 4-取代二烯进行的反应产生苯并噻唑并嘧啶作为主要产物，产率范围为 42% 至 67%，为单一非对映异构体，对映选择性在 93% 至 99% 之间。然而，用 3-取代二烯进行的相同反应得到高度对映体富集的 1,2,3,4-四氢喹啉作为主要产物，尽管具有中等的非对映选择性。
• Squaramide-catalysed enantionselective Mannich reaction of imines bearing a heterocycle with malonates
  作者：Hai-Xiao He、Da-Ming Du

  DOI：10.1039/c3ra43260b

  日期：——

  An efficient enantioselective Mannich reaction of imines bearing a heterocycle with malonates catalysed by a cinchona-based squaramide organocatalyst has been developed. This catalytic asymmetric reaction afforded the β-amino ester derivatives containing a heterocycle moiety in high yields (up to 99%) and excellent enantioselectivities (up to 98%) in most cases. The imines with an electron-withdrawing

  已经开发了一种有效的对映选择性曼尼奇反应，该亚胺带有一个由金鸡纳基方酸酰胺有机催化剂催化的丙二酸酯。该催化不对称反应在大多数情况下以高产率（高达99％）和优异的对映选择性（高达98％）提供了含有杂环部分的β-氨基酯衍生物。在该反应中，具有吸电子基团的亚胺比带有电子给体基团的亚胺具有更好的收率。
• 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.