furan-2-carbothioic acid-(4-chloro-anilide) | 64078-18-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: furan-2-carbothioic acid-(4-chloro-anilide)
• 英文别名: Furan-2-thiocarbonsaeure-(4-chlor-anilid)；Thiobrenzschleimsaeure-(4-chlor-anilid)；Thiobrenzschleimsaeure-p-chloranilid；N-(4-Chlorophenyl)-2-furancarbothioamide；N-(4-chlorophenyl)furan-2-carbothioamide
• CAS: 64078-18-8
• 化学式: C₁₁H₈ClNOS
• 分子量: 237.71
• InChiKey: UBMQWFJVDCFKTA-UHFFFAOYSA-N

物化性质

• 熔点：
  105-106 °C(Solv: ethanol (64-17-5))
• 沸点：
  335.4±48.0 °C(Predicted)
• 密度：
  1.390±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  57.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  furan-2-carbothioic acid-(4-chloro-anilide) 在 baker's yeast 、 三氯氧磷 作用下， 反应 2.0h， 生成 5-(6-chlorobenzothiazol-2-yl)furan-2-carbaldehyde
  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-(2-furylmethylene)-p-chloraniline 在 吡啶 、 sulfur 作用下， 生成 furan-2-carbothioic acid-(4-chloro-anilide)
  参考文献：
  名称：

  Farcasan; Makkay, Academia Republicii Populare Romine, Filiala Cluj, Studii si Cercetari de Chimie, 1959, vol. 10, p. 145,148

  摘要：

  DOI：

文献信息

• Jagodzinski, Tadeusz S.; Dziembowska, Teresa M.; Szczodrowska, Barbara, Bulletin des Societes Chimiques Belges, 1989, vol. 98, # 5, p. 327 - 338
  作者：Jagodzinski, Tadeusz S.、Dziembowska, Teresa M.、Szczodrowska, Barbara

  DOI：——

  日期：——
• 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.
• Aminolysis of aryl dithio-2-thiophenates and dithio-2-furoates in acetonitrile
  作者：Hyuck Keun Oh、So Young Woo、Chul Ho Shin、Ikchoon Lee

  DOI：10.1002/(sici)1097-4601(1998)30:11<849::aid-kin7>3.0.co;2-v

  日期：——

  The aminolyses of the title substrates with anilines and benzylamines are investigated in acetonitrile. A clean second-order kinetics is obtained with a first-order rate law in the amine concentration, which is uncomplicated by the fast proton transfer step. The large magnitude of rho(z) (rho(1g)) as well as rho(x) (rho(nuc)) together with relatively large positive p(xz) values is consistent with a stepwise mechanism in which thiophenolate ion expulsion from the intermediate is rate limiting. For the reactions of aryl dithio-2-thiophenates with benzylamines the magnitude of rho(x) and rho(z) values is relatively smaller suggesting that both the addition and expulsion of thiophenolate are partially rate determining. Relatively large secondary kinetic isotope effects, k(H)/k(D) greater than or equal to 1.7, with deuterated nucleophiles, support involvement a concurrent proton transfer to the departing thiophenolate ion in the transition state. (C) 1998 John Wiley & Sons, Inc.
• 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.
• Stojanac; Hahn, Croatica Chemica Acta, 1962, vol. 34, p. 237,239
  作者：Stojanac、Hahn

  DOI：——

  日期：——