(5-chlorobenzo[d]thiazol-2-yl)(4-methoxyphenyl)methanone | 1394973-47-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (5-chlorobenzo[d]thiazol-2-yl)(4-methoxyphenyl)methanone
• 英文别名: (5-Chloro-1,3-benzothiazol-2-yl)-(4-methoxyphenyl)methanone；(5-chloro-1,3-benzothiazol-2-yl)-(4-methoxyphenyl)methanone
• CAS: 1394973-47-7
• 化学式: C₁₅H₁₀ClNO₂S
• 分子量: 303.769
• InChiKey: GUUYUTSLNNTRJF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  20
• 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

• 作为产物：
  描述：

  4-甲氧基苯乙烯 在 碘 、 2-碘酰基苯甲酸 作用下， 以 二甲基亚砜 为溶剂， 生成 (5-chlorobenzo[d]thiazol-2-yl)(4-methoxyphenyl)methanone
  参考文献：
  名称：

  多路径耦合多米诺骨牌策略：无金属氧化环化，从多形式底物一锅合成2-酰基苯并噻唑

  摘要：

  已经开发了一种多途径偶联多米诺骨牌策略，用于通过多种不同的途径从多种形式的底物芳烃，芳基乙炔，2-羟基-芳族酮和甲醇中高效合成2-酰基苯并噻唑。通过逻辑耦合的氧化/杂环多米诺工艺，可以在一锅中合成多种不含金属的2-酰基苯并噻唑。

  DOI：

  10.1021/ol301921t

文献信息

• Microwave-assisted controllable synthesis of 2-acylbenzothiazoles and bibenzo[b][1,4]thiazines from aryl methyl ketones and disulfanediyldianilines
  作者：Yuquan Qi、Xiaoyu Gu、Xianqiang Huang、Guodong Shen、Bingchuan Yang、Qingpeng He、Zechun Xue、Mengcheng Du、Lilong Shi、Bing Yu

  DOI：10.1016/j.cclet.2021.05.069

  日期：2021.11

  A condition-controlled strategy for selectively synthesis of 2-acylbenzothiazoles and bibenzo[b][1,4]thiazines from aryl methyl ketones and disulfanediyldianilines was realized using I2/DMSO or I2/MeCN systems, respectively. The desired products were synthesized in only 15 min with moderate to excellent yields (50%-90%) under microwave-assisted, metal-free conditions. The strategy provides a great

  分别使用 I 2 /DMSO 或 I 2 /MeCN 系统实现了从芳基甲基酮和二硫烷二基二苯胺选择性合成 2-酰基苯并噻唑和联苯[ b ][1,4]噻嗪的条件控制策略。在微波辅助、无金属条件下，所需产物仅在 15 分钟内合成，产率中等至极好（50%-90%）。该策略为苯并噻唑和双苯并噻嗪杂环化合物的有效合成中的选择性合成应用提供了巨大优势。
• I2 promoted domino oxidative cyclization for one-pot synthesis of 2-acylbenzothiazoles via metal-free sp3 C–H functionalization
  作者：Yan-Ping Zhu、Mi Lian、Feng-Cheng Jia、Mei-Cai Liu、Jing-Jing Yuan、Qing-He Gao、An-Xin Wu

  DOI：10.1039/c2cc34561g

  日期：——

  An I(2) promoted domino protocol was developed to construct 2-acylbenzothiazoles from simple and readily available aromatic ketones/unsaturated methyl ketones and o-aminobenzenethiols. The reaction proceeded smoothly under metal-free and peroxide-free conditions.

  一个I（2）促进多米诺协议被开发，构建从简单的2 acylbenzothiazoles和容易获得的芳族酮/不饱和的甲基酮和邻 - aminobenzenethiols。该反应的金属和无过氧化物的条件下顺利进行。
• Ball-milling synthesized hydrotalcite supported Cu–Mn mixed oxide under solvent-free conditions: an active catalyst for aerobic oxidative synthesis of 2-acylbenzothiazoles and quinoxalines
  作者：Xu Meng、Xiuru Bi、Chaoying Yu、Gexin Chen、Baohua Chen、Zhenqiang Jing、Peiqing Zhao

  DOI：10.1039/c8gc01816b

  日期：——

  Ball-milling results in excellent catalytic performance of bimetallic supported catalyst Cu–Mn/HT.

  球磨法制备的双金属负载催化剂Cu-Mn/HT表现出优异的催化性能。
• New synthesis of 2-aroylbenzothiazoles <i>via</i> metal-free domino transformations of anilines, acetophenones, and elemental sulfur
  作者：Tien V. Huynh、Khang V. Doan、Ngoc T. K. Luong、Duyen T. P. Nguyen、Son H. Doan、Tung T. Nguyen、Nam T. S. Phan

  DOI：10.1039/d0ra01750g

  日期：——

  A new synthesis of 2-aroylbenzothiazoles via iodine-promoted domino transformations of anilines, acetophenones, and elemental sulfur was demonstrated. The highlights of this tandem synthesis are (1) easily available anilines and acetophenones as feedstock; (2) transition metal-free conditions; (3) inexpensive, nontoxic, easy handling, and abundant elemental sulfur as a building block. This synthetic

  展示了通过碘促进的苯胺、苯乙酮和元素硫的多米诺转变合成 2-芳酰基苯并噻唑的新方法。这种串联合成的亮点是（1）容易获得的苯胺和苯乙酮作为原料；(2)无过渡金属条件；(3)廉价、无毒、易处理、丰富的单质硫作为砌块。这种合成策略将补充这种重要的杂环支架合成中的现有方法。据我们所知，以前的文献中没有报道过从简单的苯胺、苯乙酮和元素硫形成 2-芳酰基苯并噻唑。
• 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.