benzo[d]thiazol-2-yl(3,4-dimethoxyphenyl)methanone | 115727-07-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: benzo[d]thiazol-2-yl(3,4-dimethoxyphenyl)methanone
• 英文别名: 1,3-Benzothiazol-2-yl-(3,4-dimethoxyphenyl)methanone
• CAS: 115727-07-6
• 化学式: C₁₆H₁₃NO₃S
• 分子量: 299.35
• InChiKey: SXZUIRYIVXBIRE-UHFFFAOYSA-N

物化性质

• 沸点：
  480.9±55.0 °C(Predicted)
• 密度：
  1.288±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  76.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-(3,4-dimethoxybenzyl)-benzo[d]-thiazole 在 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺-d7 为溶剂， 反应 20.0h， 以88%的产率得到benzo[d]thiazol-2-yl(3,4-dimethoxyphenyl)methanone
  参考文献：
  名称：

  苯并唑衍生物的无金属需氧氧化†

  摘要：

  2-苄基苯并噻唑和苯并咪唑在空气和碱性条件下容易氧化，以高收率得到相应的酮。指某东西的用途醋酸钯 作为催化剂，收效甚微，甚至在某些情况下收率低得多。

  DOI：

  10.1039/c3ob27404g

文献信息

• One-pot synthesis of 2-acylbenzothiazoles from 2-aminobenzenethiols and arylacetonitriles via cyclization and sequential oxidation
  作者：Shanshan Zhang、Shiwei Wang、Yuting Leng、Yangjie Wu

  DOI：10.1016/j.tetlet.2021.153300

  日期：2021.8

  via AlCl3-mediated cyclization reaction and I2-promoted sequential oxidation reaction of 2-aminobenzenethiols with arylacetonitriles was developed. This reaction proceeds smoothly with a wide range of arylacetonitriles containing different functional groups to give the corresponding products in moderate to good yields under mild conditions. Moreover, this reaction was conveniently conducted on a gram

  开发了一种有效的一锅法，通过AlCl 3介导的环化反应和 I 2促进的 2-氨基苯硫醇与芳基乙腈的顺序氧化反应获得 2-酰基苯并噻唑。该反应与各种含有不同官能团的芳基乙腈一起顺利进行，在温和的条件下以中等至良好的收率得到相应的产物。此外，该反应方便地以克规模进行，产率仍高达68%。
• A convenient synthesis of 2-acyl benzothiazoles/thiazoles from benzothiazole/thiazole and N,N'-carbonyldiimidazole activated carboxylic acids
  作者：Tonghui Huang、Xin Wu、Yongbo Yu、Lin An、Xiaoxing Yin

  DOI：10.1016/j.tetlet.2019.05.043

  日期：2019.6

  A convenient and efficient strategy for the synthesis of 2-acyl benzothiazoles/thiazoles has been developed. The treatment of benzothiazole/thiazole with allylic Grignard reagents readily generates the corresponding 2-Grignard reagents, which is followed by a reaction with N,N'-carbonyldiimidazole activated carboxylic acids to afford various 2-acyl benzothiazoles/thiazoles products. The synthetic method

  已经开发了一种方便有效的合成2-酰基苯并噻唑/噻唑的策略。用烯丙基格利雅试剂处理苯并噻唑/噻唑容易产生相应的2-格利雅试剂，然后与N，N′-羰基二咪唑活化的羧酸反应，得到各种2-酰基苯并噻唑/噻唑产物。该合成方法适用于多种羧酸，并且在温和的反应条件下，可以很容易地获得2-酰基苯并噻唑/噻唑。
• An Efficient Copper-Mediated Route for the Synthesis of 2-Substituted Benzothiazoles from Dithioesters and Investigation of Their Antibacterial Activities
  作者：Maralinganadoddi P. Sadashiva、Kodipura P. Sukrutha、Kuppalli R. Kiran、Kodagahally T. Gunashree、Shivakumar Divyashree、Prerana Purusotham、Marikunte Y. Sreenivasa

  DOI：10.1055/a-2193-5436

  日期：2024.2

  one-pot synthesis of 2-aryl/2-aroylbenzothiazoles through copper-mediated condensation of 2-chloroanilines with dithioesters has been developed. The method provides good isolated yields and exhibits broad functional group tolerance, accommodating both electron-donating and electron-withdrawing groups on the substrates. A series of synthesized compounds was evaluated for their antibacterial activity against

  通过铜介导的 2-氯苯胺与二硫酯的缩合，开发出了一种有效的一锅法合成 2-芳基/2-芳酰基苯并噻唑的方法。该方法提供了良好的分离产率，并表现出广泛的官能团耐受性，可容纳底物上的给电子基团和吸电子基团。评估了一系列合成化合物对肺炎克雷伯菌、铜绿假单胞菌和副伤寒沙门氏菌的抗菌活性。在该系列中，三种化合物对所测试的病原体表现出显着的抑制作用，其中一种还在琼脂井扩散测定和肉汤微量稀释测定中显示出作为有效化合物的潜力。此外，在结晶紫测定和MTT测定中，这三种化合物在浓度为10 mM时对病原体生物膜的形成表现出强烈的抑制作用。这些发现凸显了这些化合物具有前景的抗菌和抗生物膜特性，表明它们作为针对所测试病原体的潜在治疗剂进行进一步研究的潜力。
• Chemoselective Copper-Catalyzed Acylation of Benzothiazoles with Aryl Methyl Ketones
  作者：Qiang Feng、Qiuling Song

  DOI：10.1002/adsc.201400240

  日期：2014.8.11

  AbstractA copper(I) iodide‐catalyzed, highly efficient acylation of benzothiazoles with aryl methyl ketones as carbonyl sources under a nitrogen atmosphere was developed. This is an unprecedented protocol and an extremely efficient method for the selective synthesis of 2‐acylbenzothiazoles from commercially available, cheap starting materials with excellent chemoselectivity, good functional group tolerability and high turnover numbers (up to 14,200); also scaling up to 160 mmol without loss of the efficiency is possible. A variety of 2‐acylbenzothiazoles was smoothly prepared in good to excellent yields from aryl methyl ketones and benzothiazoles by a one‐pot domino protocol of combined sp3 CH oxidation, ring opening, and condensation.magnified image
• Metal-free aerobic oxidation of benzazole derivatives
  作者：Aurélie Dos Santos、Laurent El Kaïm、Laurence Grimaud

  DOI：10.1039/c3ob27404g

  日期：——

  2-Benzyl benzothiazoles and benzimidazoles are easily oxidized under air and basic conditions to give the corresponding ketones in good yields. The use of palladium acetate as a catalyst has little effect and even gives, in some cases, much lower yields.

  2-苄基苯并噻唑和苯并咪唑在空气和碱性条件下容易氧化，以高收率得到相应的酮。指某东西的用途醋酸钯 作为催化剂，收效甚微，甚至在某些情况下收率低得多。