5-(6-甲基-1,3-苯并噻唑-2-基)呋喃-2-甲醛 | 63400-69-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻唑类
• 中文名称: 5-(6-甲基-1,3-苯并噻唑-2-基)呋喃-2-甲醛
• 英文名称: 5-(6-methylbenzothiazol-2-yl)furan-2-carbaldehyde
• 英文别名: 5-(6-Methyl-1,3-benzothiazol-2-yl)furan-2-carbaldehyde
• CAS: 63400-69-1
• 化学式: C₁₃H₉NO₂S
• 分子量: 243.286
• InChiKey: VTNRYZXDGQWZOC-UHFFFAOYSA-N

物化性质

• 熔点：
  168 °C
• 沸点：
  441.9±55.0 °C(Predicted)
• 密度：
  1.334±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  71.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-(6-甲基-1,3-苯并噻唑-2-基)呋喃-2-甲醛 在 盐酸 、 4-二甲氨基吡啶 、 三乙胺 、 zinc(II) iodide 作用下， 以 吡啶 、 二氯甲烷 、 乙腈 为溶剂， 反应 0.25h， 生成 5-(6-methylbenzothiazol-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-(p-tolyl)furan-2-carboxamide 在 baker's yeast 、 tetraphosphorus decasulfide 、 三氯氧磷 作用下， 以 吡啶 为溶剂， 反应 2.0h， 生成 5-(6-甲基-1,3-苯并噻唑-2-基)呋喃-2-甲醛
  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

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.
• BIOORGANIC SYNTHESIS OF SOME (5-BENZOTHIAZOL-2-YL -FURAN-2-YL)- METHANOLS IN CELL CATALYSIS USING SACCHAROMYCES CEREVISIAE
  作者：Florin-Dan Irimie、Csaba Paizs、Cornelia Majdik、Monica Toşa

  DOI：10.1515/hc.2002.8.5.489

  日期：2002.1
• FARCASAN V.; PAIN F.; INSAN C., STUD. UNIV. BABES-BOLYAI, SER. CHEM. <SUBC-AB>, 1977, 22, 15-18
  作者：FARCASAN V.、 PAIN F.、 INSAN C.

  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.