4-Chlorophenoxysulphonyl isocyanate | 14793-41-0

• 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: 4-Chlorophenoxysulphonyl isocyanate
• 英文别名: p-chlorophenoxysulfonyl isocyanate；isocyanate de chloro-4 phenoxysulfonyle；4-Chlor-phenoxy-sulfonyl-isocyanat；4-Chlorophenoxysulphonylisocyanate；(4-chlorophenyl) N-(oxomethylidene)sulfamate
• CAS: 14793-41-0
• 化学式: C₇H₄ClNO₄S
• 分子量: 233.632
• InChiKey: ATDQVLZAIRTYNX-UHFFFAOYSA-N

物化性质

• 沸点：
  91-95 °C(Press: 1 Torr)
• 密度：
  1.50±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  81.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-Chlorophenoxysulphonyl isocyanate 在 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 氯苯 为溶剂， 反应 4.0h， 生成 3-(p-chlorophenoxysulfonyl)-4-hydroxymethyl-1,3-oxazolidin-2-one
  参考文献：
  名称：

  Preparation and Antimicrobial Studies of Acyclic Sulfamates.

  摘要：

  A series of acyclic sulfamates have been prepared and tested for antimicrobial activity. Thus, the oxysulfonyl isocyanates, ROSO2NCO (1a, R = 4-methoxyphenyl; 1b, R = phenyl; 1c, R = 4-chlorophenyl and 1d, R = 2,2,2-trifluoroethyl) have been prepared in 76-91% yield from chlorosulfonyl isocyanate. Treatment of lad with glycidol gave the glycidyl carbamates 2a-d. Internal cyclisation afforded the corresponding 3-hydroxymethyl-2-oxazolidinones 3a d, which in turn were hydrolysed to give the free amino alcohols 4a-d. The yields were in the range 39-85%. A preliminary agar diffusion test of 2a-d, 3a d, 4a d indicated 2a-d and 3e to be possible antimicrobial agents. A more thorough analysis of these compounds revealed a minimum inhibition concentration (MIC) of 128 and 64 mg 1(-1) for glycidyl p-methoxyphenoxysulfonylcarbamate (2a) and glycidyl phenoxysulfonylcarbamate (2b) respectively, against Branhamella catarrhalis.

  DOI：

  10.3891/acta.chem.scand.53-0446
• 作为产物：
  描述：

  氯磺酰异氰酸酯 、 对氯苯酚 以 氯苯 为溶剂， 以72%的产率得到4-Chlorophenoxysulphonyl isocyanate
  参考文献：
  名称：

  Preparation and Antimicrobial Studies of Acyclic Sulfamates.

  摘要：

  A series of acyclic sulfamates have been prepared and tested for antimicrobial activity. Thus, the oxysulfonyl isocyanates, ROSO2NCO (1a, R = 4-methoxyphenyl; 1b, R = phenyl; 1c, R = 4-chlorophenyl and 1d, R = 2,2,2-trifluoroethyl) have been prepared in 76-91% yield from chlorosulfonyl isocyanate. Treatment of lad with glycidol gave the glycidyl carbamates 2a-d. Internal cyclisation afforded the corresponding 3-hydroxymethyl-2-oxazolidinones 3a d, which in turn were hydrolysed to give the free amino alcohols 4a-d. The yields were in the range 39-85%. A preliminary agar diffusion test of 2a-d, 3a d, 4a d indicated 2a-d and 3e to be possible antimicrobial agents. A more thorough analysis of these compounds revealed a minimum inhibition concentration (MIC) of 128 and 64 mg 1(-1) for glycidyl p-methoxyphenoxysulfonylcarbamate (2a) and glycidyl phenoxysulfonylcarbamate (2b) respectively, against Branhamella catarrhalis.

  DOI：

  10.3891/acta.chem.scand.53-0446
• 作为试剂：
  描述：

  乙醇 、 8-Methyl-4-oxo-3-propyl-1,4-dihydro-quinoline-2-carboxylic acid ethyl ester 在 盐酸 、 4-Chlorophenoxysulphonyl isocyanate 作用下， 生成 4-Amino-8-methyl-3-propyl-quinoline-2-carboxylic acid ethyl ester; compound with sulfuric acid monoethyl ester
  参考文献：
  名称：

  A Simple One-Pot Conversion of Alkyl 4-Oxo-1,4-dihydroquinoline-2-carboxylates to 4-Aminoquinoline-2-carboxylates using Reactive Isocyanates

  摘要：

  DOI：

  10.1055/s-1984-31080

文献信息

• Addition of various unsaturated alcohols to sulfonylisocyanate derivatives: Synthesis of new unsaturated N-sulfonyl carbamates
  作者：Ahlem Radhouani、Mohamed Beji

  DOI：10.1080/10426507.2015.1072186

  日期：2016.5.3

  GRAPHICAL ABSTRACT Abstract The synthesis of new unsaturated N-sulfonylcarbamates by the addition of unsaturated alcohols to aroxy(alkoxy)sulfonylisocyanates is reported. The reaction is carried out at room temperature in the presence or absence of solvent, depending on the nature of the starting alcohol. The products were obtained in good yields and characterized with IR, 1H, and 13C NMR and HRMS

  图形摘要 摘要 报道了通过将不饱和醇加成到芳氧基（烷氧基）磺酰基异氰酸酯上来合成新的不饱和 N-磺酰基氨基甲酸酯。根据起始醇的性质，该反应在室温下在溶剂存在或不存在下进行。产品以良好的收率获得，并通过 IR、1H 和 13C NMR 和 HRMS 分析进行表征。
• Reaction of Acids and Diacids with Aroxy(alcoxy)sulfonyl Isocyanates: Synthesis of <i>N</i>-Acylsulfamates, Disulfamates, and <i>N</i>,<i>N</i>′-Disulfonylureas
  作者：Hassen Sbihi、Mohamed Beji、Ahmed Baklouti

  DOI：10.1080/00397910802219114

  日期：2008.7.24

  Abstract Reaction of carboxylic acids with aroxy(alcoxy)sulfonylisocyanates allowed the preparation of the corresponding aroxy(alcoxy) N-acylsulfamates. With succinic diacid, the same reaction yielded the corresponding N, N′-diacylsulfamates, whereas the N, N′-disulfonylureas were obtained by reaction of maleic or fumaric diacids.

  摘要 羧酸与芳氧基（烷氧基）磺酰基异氰酸酯反应可以制备相应的芳氧基（烷氧基）N-酰基氨基磺酸盐。对于琥珀二酸，同样的反应产生相应的 N, N'-二酰基氨基磺酸盐，而 N, N'-二磺酰脲是通过马来酸或富马酸二酸的反应获得的。
• Certain hydrolysis or reductive cleavage reaction involving
  申请人：Fisons plc

  公开号：US04471119A1

  公开（公告）日：1984-09-11

  There is described a process for the production of a compound of formula I, ##STR1## in which R is hydrogen or alkyl Cl to 6, and R.sub.5 and R.sub.10, which may be the same or different, are each hydrogen or alkyl Cl to 6, or a pharmaceutically acceptable derivative thereof, which comprises removal of an activating group from a compound of formula II, ##STR2## or a suitable derivative thereof, in which R, R.sub.5 and R.sub.10 are as defined above, and X represents an activating group, and if desired or necessary converting the resulting compound of formula I to a pharmaceutically acceptable derivative thereof, or vice versa. There is also described a process for the production of a compound of formula II in which R is hydrogen, or a suitable derivative thereof, which comprises reaction of a compound of formula III, ##STR3## or a suitable derivative thereof, in which R.sub.5 and R.sub.10 are as defined above, with a compound of formula IV, X--N.dbd.C.dbd.O IV in which X is as defined above.

  描述了一种生产化合物I的方法，其中R是氢或烷基Cl至6，而R.sub.5和R.sub.10，可以相同也可以不同，分别是氢或烷基Cl至6，或其药学上可接受的衍生物，该方法包括从化合物II中去除一个活化基团，其中R、R.sub.5和R.sub.10如上所定义，X代表一个活化基团，如有需要，将得到的化合物I转化为其药学上可接受的衍生物，或反之亦然。还描述了一种生产化合物II的方法，其中R是氢，或其适当的衍生物，该方法包括使化合物III与化合物IV反应。
• Synthesis of F-alkyl bis(N-aroxy or alkoxysulfonyl)dicarbamates
  作者：H. Sbihi、M. Beji、A. Baklouti

  DOI：10.1016/s0022-1139(00)00282-7

  日期：2000.7

  The synthesis of F-alkyl bis(N-aroxy or alkoxysulfonyl)dicarbamates has been achieved at room temperature by the action of F-alkyldiols on aroxy or alkoxysulfonyl isocyanates.

  F-烷基双（N-芳氧基或烷氧基磺酰基）二氨基甲酸酯的合成是在室温下通过F-烷基二醇对芳氧基或烷氧基磺酰基异氰酸酯的作用而实现的。
• 6-substituted amino-4H-pyrano(3,2-G)quinoline-2,8-dicarboxylic acid
  申请人：Fisons plc

  公开号：US04614802A1

  公开（公告）日：1986-09-30

  Disclosed are compounds of the formula ##STR1## in which R is hydrogen or alkyl C.sub.1 to C.sub.6 and R.sub.5 and R.sub.10, which may be the same or different, are hydrogen or alkyl C.sub.1 to C.sub.6, X represents a group --AR.sub.6, A is CO or SO.sub.2 and R.sub.6 is halogen, C.sub.1 -C.sub.6 haloalkyl, C.sub.1 -C.sub.6 alkoxy, C.sub.6 -C.sub.9 aryloxy or phenyl optionally substituted by C.sub.1 -C.sub.6 alkyl, and salts, esters, and amides which are intermediates to anti-allergic compounds.

  本发明揭示了化合物的结构公式为##STR1##其中，R是氢原子或C.sub.1到C.sub.6的烷基，R.sub.5和R.sub.10可以相同也可以不同，是氢原子或C.sub.1到C.sub.6的烷基，X代表--AR.sub.6基团，A是CO或SO.sub.2，R.sub.6是卤素，C.sub.1-C.sub.6卤代烷基，C.sub.1-C.sub.6烷氧基，C.sub.6-C.sub.9芳氧基或苯环，可选择用C.sub.1-C.sub.6烷基取代的苯环，以及用于制备抗过敏化合物的盐，酯和酰胺等中间体。