1-(benzo[d]thiazol-2-yl)butan-1-one | 41881-84-9

• 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: 1-(benzo[d]thiazol-2-yl)butan-1-one
• 英文别名: 1-Butanone, 1-(2-benzothiazolyl)-；1-(1,3-benzothiazol-2-yl)butan-1-one
• CAS: 41881-84-9
• 化学式: C₁₁H₁₁NOS
• 分子量: 205.28
• InChiKey: AZRWKQJNMVITAR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  58.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1-(1,3-苯并噻唑-2-基)-1-丁醇 在 chromium(VI) oxide 、 溶剂黄146 作用下， 生成 1-(benzo[d]thiazol-2-yl)butan-1-one
  参考文献：
  名称：

  Subarowskii; Rikel'man, Zhurnal Obshchei Khimii, 1951, vol. 21, p. 2205,2207, 2208, 2209

  摘要：

  DOI：

文献信息

• Photoredox-Mediated Direct Cross-Dehydrogenative Coupling of Heteroarenes and Amines
  作者：Jianyang Dong、Qing Xia、Xueli Lv、Changcun Yan、Hongjian Song、Yuxiu Liu、Qingmin Wang

  DOI：10.1021/acs.orglett.8b02389

  日期：2018.9.21

  A photoredox-mediated direct cross-dehydrogenative coupling reaction to accomplish α-aminoalkylation of N-heteroarenes is reported. This mild reaction has a broad substrate scope, offers the first general method for synthesis of aminoalkylated N-heteroarenes without the need for substrate prefunctionalization, and is scalable to the gram level. Furthermore, the reaction was found to be applicable to

  报道了光氧化还原介导的直接交叉脱氢偶联反应以完成N-杂芳烃的α-氨基烷基化。这种温和的反应具有广泛的底物范围，提供了无需进行底物预官能化即可合成氨基烷基化N-杂芳烃的第一种通用方法，并且可扩展至克级。此外，发现该反应除了胺（即，醚，醛，甲酰胺，对二甲苯和烷烃）以外还适用于其他氢供体，因此能够制备带有各种取代基的N-杂芳烃。
• Regulable cross-coupling of alcohols and benzothiazoles <i>via</i> a noble-metal-free photocatalyst under visible light
  作者：Zi-Tong Pan、Xu-Kuan Qi、Qian Xiao、Xi-Wen Liang、Jian-Ji Zhong、Jing-Xin Jian、Qing-Xiao Tong

  DOI：10.1039/d2cc03234a

  日期：——

  This work demonstrated a regulable cross-coupling of alcohols with benzothiazole under visible light. Two kinds of products, alkyl- and acetyl-derived benzothiazoles, are achieved with high yields up to 99% in Ar and 90% in air, respectively.

  这项工作展示了一种可调节的醇与苯并噻唑的交叉偶联反应，在可见光下进行。通过此反应，可以得到两种产物，即烷基和乙酰基衍生的苯并噻唑，分别在气氛和空气中的收率高达99％和90％。
• Self-photocatalyzed regulable alkylation of 2<i>H</i>-benzothiazoles with diverse aliphatic C–H donors
  作者：Jiadi Zhou、Chaodong Wang、Lei Huang、Can Luo、Shilu Ye、Ning Xu、Yunsheng Zhu、Li Liu、Quanlei Ren、Zhi Chen、Shengjie Song、Jianjun Li

  DOI：10.1039/d2gc01225a

  日期：——

  catalysis and hydrogen atom transfer to achieve the alkylation of 2H-benzothiazoles with alcohols, ethers, lactams, amides and alkane, which features broad substrate scope and excellent functional group compatibility. Notably, alcohols can be used not only as hydroxyalkylating reagents, but also as dehydroxyalkylating reagents in this regulable alkylation protocol. The previous elusive self-photocatalytic

  在这里，我们报道了一种温和有效的方法，将自光氧化还原催化和氢原子转移相结合，实现 2 H-苯并噻唑与醇、醚、内酰胺、酰胺和烷烃的烷基化，具有广泛的底物范围和优异的官能团相容性。值得注意的是，醇不仅可以用作羟烷基化试剂，还可以在这种可调节的烷基化方案中用作脱羟烷基化试剂。研究了以前难以捉摸的自光催化机理，并报道了这种催化烷基化的初步结果。
• Ag-catalyzed acylation of N-heterocycles in aqueous solution
  作者：Yingyue Song、Zehui Yu、Wengui Wang、Shoufeng Wang

  DOI：10.1016/j.tet.2023.133518

  日期：2023.7

  A silver-catalyzed Minisci-type acylation reaction is reported here. Acylation of electron-deficient N-heterocycles is achieved in aqueous solution through dehydrogenation cross-coupling of aldehydes and N-heteroarenes in open air without external Brønsted acid. Selectfluor® is used as a mild oxidant. This method has been successfully employed in acylation of a variety of N-heteroarenes with aldehydes

  本文报道了银催化的 Minisci 型酰化反应。缺电子N-杂环的酰化是在水溶液中通过醛和N-杂芳烃在露天中脱氢交叉偶联而实现的，无需外部布朗斯台德酸。Selectflu® 用作温和氧化剂。该方法已成功应用于多种N-杂芳烃与醛的酰化。该策略提供了一种有效且温和的 N-杂芳烃酰化方法。
• Peroxides as “Switches” of Dialkyl <i>H</i>-Phosphonate: Two Mild and Metal-Free Methods for Preparation of 2-Acylbenzothiazoles and Dialkyl Benzothiazol-2-ylphosphonates
  作者：Xiao-Lan Chen、Xu Li、Ling-Bo Qu、Yu-Chun Tang、Wen-Peng Mai、Dong-Hui Wei、Wen-Zhu Bi、Li-Kun Duan、Kai Sun、Jian-Yu Chen、Dian-Dian Ke、Yu-Fen Zhao

  DOI：10.1021/jo501791n

  日期：2014.9.5

  Two mild and metal-free methods for the preparation of two kinds of important benzothiazole derivatives, 2-acylbenzothiazoles and dialkyl benzothiazol-2-ylphosphonates, respectively, were developed. The diallcyl H-phosphonate (RO)(2)P(O)H exists in equilibrium with its tautomer dialkyl phosphite (RO)(2)POH. TBHP triggered alpha-carbon-centered phosphite radical formation, whereas DTBP triggered phosphorus-centered phosphonate radical formation. The two types of radicals led respectively to two different reaction processes, the direct C-2-acylation of benzothiazoles and C-2-phosphonation of benzothiazoles.