benzo[d]thiazol-2-yl(2-methoxyphenyl)methanone | 445298-04-4

• 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(2-methoxyphenyl)methanone
• 英文别名: 1,3-Benzothiazol-2-yl-(2-methoxyphenyl)methanone
• CAS: 445298-04-4
• 化学式: C₁₅H₁₁NO₂S
• 分子量: 269.324
• InChiKey: MBFTVGLEBWJQHL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  19
• 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：
  67.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  benzo[d]thiazol-2-yl(2-methoxyphenyl)methanone 在 盐酸羟胺 、 sodium acetate 作用下， 以80 %的产率得到
  参考文献：
  名称：

  一种杂环肟类化合物及其制备方法和应用、组合物

  摘要：

  本发明属于农药技术领域，具体涉及一种杂环肟类化合物及其制备方法和应用、组合物。本发明提供了一种杂环肟类化合物，具有式1所示结构。本发明提供的杂环肟类化合物以杂环二芳肟结构作为骨架结构，且与肟基相连的一个杂芳基为取代或为取代的苯并噻唑基，由此得到的苯并噻唑肟类化合物通过骨架结构上的肟基与杂环基共同作用，能够对植物真菌病害有良好的抑制作用，对新农药的创制有积极意义。#imgabs0#

  公开号：

  CN116987047A
• 作为产物：
  描述：

  1,1-dibromo-2-(2-methoxyphenyl)ethene 、 双(2-氨基苯基)二硫 在 copper(II) bis(trifluoromethanesulfonate) 、 caesium carbonate 作用下， 以 二甲基亚砜 为溶剂， 以39%的产率得到benzo[d]thiazol-2-yl(2-methoxyphenyl)methanone
  参考文献：
  名称：

  Synthesis of 2-Acylbenzothiazoles via the Cu(OTf)2-Catalyzed Tandem Reaction of β,β-Dihalidestyrenes with 2,2′-Disulfanediyldianilines

  摘要：

  A new method has been developed for the one-pot construction of 2-acylbenzothiazoles via the Cu(OTf)(2)-catalyzed tandem reaction of ,-dihalidestyrenes with 2,2-disulfane-diyldianilines. A variety of different dihalidestyrenes and diphenyldisulfanes were efficiently converted into the corresponding 2-acylbenzothiszole derivatives in the presence of Cu(OTf)(2). Most importantly, this protocol allowed for the long chain 1,1-dibromohept-1-ene to be converted into the corresponding 2-hexylbenzo[d]thiazole in moderate yield.

  DOI：

  10.1055/s-0033-1340288
• 作为试剂：
  描述：

  2,2,6,6-四甲基哌啶氧化物 、 双(2-氨基苯基)二硫 在 benzo[d]thiazol-2-yl(2-methoxyphenyl)methanone 、 2-溴苯乙酮 作用下， 生成
  参考文献：
  名称：

  离子液体与微波辐射协同可持续制备2-酰基苯并噻唑

  摘要：

  微波辐射（MW）和离子液体（IL）是制备增值化学品的两种最有前途的相对绿色合成方法。在此，首次以市售α-溴苯乙酮和二硫烷-二基-二苯胺为原料，在无金属和额外添加剂的条件下，通过离子液体和微波辐射的配合合成了一系列2-酰基苯并噻唑衍生物。已经提出了一种涉及连续 IL 诱导烯醇化的合理机制。

  DOI：

  10.1039/d4ob00315b

文献信息

• Oxidant/Solvent-Controlled I₂-Catalyzed Domino Annulation for Selective Synthesis of 2-Aroylbenzothiazoles and 2-Arylbenzothiazoles under Metal-Free Conditions
  作者：Renchao Ma、Yuxin Ding、Rener Chen、Zhiming Wang、Lei Wang、Yongmin Ma

  DOI：10.1021/acs.joc.0c02095

  日期：2021.1.1

  A simple and practical domino protocol for the selective synthesis of 2-aroylbenzothiazoles and 2-aryl benzothiazoles catalyzed by I2 is developed under metal-free conditions. The reaction outcomes are exclusively controlled by the reaction oxidant/medium. With DMSO employed as both the solvent and the oxidant, an oxidation of aromatic methyl ketones takes precedence over the condensation with 2-aminobenzenethiols

  在无金属条件下开发了一种简单实用的多米诺协议，该协议可选择性合成I 2催化的2-芳酰基苯并噻唑和2-芳基苯并噻唑。反应结果完全由反应氧化剂/介质控制。在同时使用DMSO作为溶剂和氧化剂的情况下，芳族甲基酮的氧化作用优先于与2-氨基苯硫醇的缩合反应。另一方面，当反应在PhNO 2或含PhNO 2的1,4-二恶烷中进行时，芳族甲基酮与2-氨基苯硫醇的缩合反应优先形成亚胺，随后甲基被氧化由酮得到2-芳基苯并噻唑的唯一产物。PhNO 2 / I2首次提出共催化体系。
• Regioselectivity in the Addition of Grignard Reagents to Bis(2-benzothiazolyl) Ketone: C- vs. O-Alkylation Using Aryl Grignard Reagents
  作者：Carla Boga、Gabriele Micheletti

  DOI：10.1002/ejoc.201000764

  日期：2010.10

  The reaction between bis(2-benzothiazolyl) ketone (1) and a series of ring-substituted phenyl Grignard reagents gives, in considerable amount, the unexpected O-alkylation product derived from the attack of the Grignard reagent to the carbonyl oxygen atom, thus extending the range of rarely reported cases in which O-alkylation can occur. The expected classic 1,2-addition product and that derived from

  双（2-苯并噻唑基）酮（1）与一系列环取代的苯基格氏试剂反应，得到大量意想不到的O-烷基化产物，来源于格氏试剂对羰基氧原子的攻击，因此扩大了很少报道的可能发生 O-烷基化的情况的范围。预期的经典 1,2-加成产物和衍生自 O-烷基化的产物以依赖于苯环上的取代基的相对摩尔比获得。双（2-苯并噻唑基）芳基甲醇是 1 羰基的经典 1,2-加成产物，通过替代合成路线以高产率获得，该路线允许 O-与 C-烷基化竞争施加的限制为克服。
• 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
• Ink composition, ink jet recording method, printed material, method of producing planographic printing plate, and planographic printing plate
  申请人：FUJIFILM Corporation

  公开号：EP1688466B1

  公开（公告）日：2008-11-26
• Synthesis of 2-Acylbenzothiazoles via the Cu(OTf)2-Catalyzed Tandem Reaction of β,β-Dihalidestyrenes with 2,2′-Disulfanediyldianilines
  作者：Chen-Liang Deng、Zeng-Le Zhou、Tao Fang、Ri-Yuan Tang、Xing-Guo Zhang

  DOI：10.1055/s-0033-1340288

  日期：——

  A new method has been developed for the one-pot construction of 2-acylbenzothiazoles via the Cu(OTf)(2)-catalyzed tandem reaction of ,-dihalidestyrenes with 2,2-disulfane-diyldianilines. A variety of different dihalidestyrenes and diphenyldisulfanes were efficiently converted into the corresponding 2-acylbenzothiszole derivatives in the presence of Cu(OTf)(2). Most importantly, this protocol allowed for the long chain 1,1-dibromohept-1-ene to be converted into the corresponding 2-hexylbenzo[d]thiazole in moderate yield.