6-chloro-2-(furan-2-yl)benzo[d]thiazole | 1568-21-4

• 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-chloro-2-(furan-2-yl)benzo[d]thiazole
• 英文别名: 6-Chlor-2-furyl-(2)-benzthiazol；6-chloro-2-furan-2-yl-benzothiazole；Benzothiazole,6-chloro-2-(2-furanyl)-；6-chloro-2-(furan-2-yl)-1,3-benzothiazole
• CAS: 1568-21-4
• 化学式: C₁₁H₆ClNOS
• 分子量: 235.694
• InChiKey: IOULGGRTUIAEGP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  54.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-chloro-2-(furan-2-yl)benzo[d]thiazole 在 盐酸 、 4-二甲氨基吡啶 、 三乙胺 、 zinc(II) iodide 、 三氯氧磷 作用下， 以 吡啶 、 二氯甲烷 、 乙腈 为溶剂， 反应 2.25h， 生成 5-(6-chlorobenzothiazol-2-yl)furan-2-ylcyanomethyl acetate
  参考文献：
  名称：

  Candida antarctica lipase A in the dynamic resolution of novel furylbenzotiazol-based cyanohydrin acetates

  摘要：

  A series of novel (R)-furylbenzotiazol-based cyanohydrin acetates were prepared in over 90% isolated yields from the corresponding furancarbaldehydes. The one-pot method combines a basic resin to produce hydrogen cyanide from acetone cyanohydrin, an equilibrium between the formation and decomposition of furylbenzotiazol-based cyanohydrins and the unique enantioselectivity of Candida antarctica lipase A, allowing the acylation of (R)-cyanohydrins in the presence of vinyl acetate in anhydrous acetonitrile. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00025-9
• 作为产物：
  描述：

  N-(4-chlorophenyl)furan-2-carboxamide 在 劳森试剂 、 4-硝基碘苯 、 Oxone 、 三氟甲磺酸 作用下， 反应 8.0h， 生成 6-chloro-2-(furan-2-yl)benzo[d]thiazole
  参考文献：
  名称：

  Organocatalytic Syntheses of Benzoxazoles and Benzothiazoles using Aryl Iodide and Oxone via C–H Functionalization and C–O/S Bond Formation

  摘要：

  An organocatalytic protocol for the syntheses of 2-substituted benzoxazoles and benzothiazoles is described from alkyl-/arylanilides and alkyl-/arylthioanilides using 1-iodo-4-nitrobenzene as catalyst and oxone as an inexpensive and environmentally safe terminal oxidant at room temperature in air via oxidative C-H functionalization and C-O/S bond formation. The procedure is simple and general and provides an effective route for the construction of functionalized 2-alkyl-/arylbenzoxazoles and 2-alkyl-/arylbenzothiazoles with moderate to high yields. The synthetic and mechanistic aspects have been described.

  DOI：

  10.1021/jo501216h

文献信息

• CaL-B a highly selective biocatalyst for the kinetic resolution of furylbenzthiazole-2-yl-ethanols and acetates
  作者：László Csaba Bencze、Csaba Paizs、Monica Ioana Toşa、Maria Trif、Florin Dan Irimie

  DOI：10.1016/j.tetasy.2010.06.010

  日期：2010.8

  A highly stereoselective enzymatic kinetic resolution of novel various substituted racemic furylbenzthiazole-2-yl-ethanols and their acetates has been developed. Both processes, the enzymatic acylation of the racemic alcohols and the enzymatic methanolysis of racemic acetates yielded highly enantiomerically enriched (ee >98%) resolution product, when CaL-B was used as a biocatalyst in acetonitrile. The absolute configuration of the obtained (R)-(+)-1-(5-(4-chlorobenzo[d]thiazol-2-yl)furan-2-y1)ethanol was determined by a detailed H-1 NMR study of rac- and (+)-1-(5-(4-chlorobenzo[d]thiazol-2-yl)furan-2-yl)ethanol Mosher derivatives. (C) 2010 Elsevier Ltd. All rights reserved.
• FISER-JAKIC, L.;JAKOPCIC, K., CROAT. CHEM. ACTA, 1981, 54, N 2, 245-248
  作者：FISER-JAKIC, L.、JAKOPCIC, K.

  DOI：——

  日期：——
• Candida antarctica lipase A in the dynamic resolution of novel furylbenzotiazol-based cyanohydrin acetates
  作者：Csaba Paizs、Monica Toşa、Cornelia Majdik、Petri Tähtinen、Florin Dan Irimie、Liisa T. Kanerva

  DOI：10.1016/s0957-4166(03)00025-9

  日期：2003.3

  A series of novel (R)-furylbenzotiazol-based cyanohydrin acetates were prepared in over 90% isolated yields from the corresponding furancarbaldehydes. The one-pot method combines a basic resin to produce hydrogen cyanide from acetone cyanohydrin, an equilibrium between the formation and decomposition of furylbenzotiazol-based cyanohydrins and the unique enantioselectivity of Candida antarctica lipase A, allowing the acylation of (R)-cyanohydrins in the presence of vinyl acetate in anhydrous acetonitrile. (C) 2003 Elsevier Science Ltd. All rights reserved.
• Organocatalytic Syntheses of Benzoxazoles and Benzothiazoles using Aryl Iodide and Oxone via C–H Functionalization and C–O/S Bond Formation
  作者：Santhosh Kumar Alla、Pradeep Sadhu、Tharmalingam Punniyamurthy

  DOI：10.1021/jo501216h

  日期：2014.8.15

  An organocatalytic protocol for the syntheses of 2-substituted benzoxazoles and benzothiazoles is described from alkyl-/arylanilides and alkyl-/arylthioanilides using 1-iodo-4-nitrobenzene as catalyst and oxone as an inexpensive and environmentally safe terminal oxidant at room temperature in air via oxidative C-H functionalization and C-O/S bond formation. The procedure is simple and general and provides an effective route for the construction of functionalized 2-alkyl-/arylbenzoxazoles and 2-alkyl-/arylbenzothiazoles with moderate to high yields. The synthetic and mechanistic aspects have been described.