N-甲基-N-(氯硫代)对甲苯磺酰胺 | 52913-45-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: N-甲基-N-(氯硫代)对甲苯磺酰胺
• 英文名称: N-chlorothio-N-methyl-4-toluenesulphonamide
• 英文别名: N-chlorothio-N-methyl-p-toluenesulfonamide；S-chloro-N-methyl-N-(toluene-4-sulfonyl)-thiohydroxylamine；methyl-(toluene-4-sulfonyl)-amidosulfenyl chloride；(p-Toluol-sulfonsaeure-methylamido)-N-sulfonsaeurechlorid；Amidosulfenyl chloride, methyl((4-methylphenyl)sulfonyl)-；[methyl-(4-methylphenyl)sulfonylamino] thiohypochlorite
• CAS: 52913-45-8
• 化学式: C₈H₁₀ClNO₂S₂
• 分子量: 251.758
• InChiKey: NAWQKWLDGDPPJR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 海关编码：
  2935009090

反应信息

• 作为反应物：
  描述：

  N-甲基-N-(氯硫代)对甲苯磺酰胺 在 magnesium bromide 作用下， 以 二氯甲烷 、 氯仿 、 水 为溶剂， 反应 4.5h， 生成 benzhydryl (6R,7Z)-3-(acetyloxymethyl)-7-[methyl-(4-methylphenyl)sulfonylamino]sulfanylimino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
  参考文献：
  名称：

  Toward the Development of a Cephalosporin-Based Dual-Release Prodrug for Use in ADEPT

  摘要：

  In previous work we have shown that a cephalosporin structure bearing an S-aminosulfenimine at the 7-position behaved as a beta-lactamase-dependent dual-release prodrug. Scission of the beta-lactam ring of such a structure led to the rapid loss of the sulfur-attached side chain moiety via an intramolecular displacement, while the T-group was lost via the well-established elimination process at that position. In the present work we report on an evaluation of the scope and limitations of exploiting the S-aminosulfenimine functionality to generate a cephalosporin-based prodrug incorporating two biologically active components. Starting from 7-ACA, a viable synthetic cycle was put in place that avoided formation of the Delta(2) isomer throughout and that allowed incorporation of aminoglutethimide at the 3'-position and of a tosyl S-aminosulfenimine at the 7-position. The direct incorporation of a biologically active sulfonamide (ethoxzolamide) or a sulfamate (coumate) at this latter position was not achieved as a result of the difficulty of generating the corresponding sulfur diimides. An indirect route for the formation of an S-aminosulfenimine was put in place, as was a general method of alkylation (Mitsunobu reaction) of the tosyl S-ammosulfenimine following its incorporation.

  DOI：

  10.1021/jo048970i
• 作为产物：
  描述：

  N-甲基对甲苯磺酰胺 在 二氯化硫 作用下， 以 氯仿 为溶剂， 生成 N-甲基-N-(氯硫代)对甲苯磺酰胺
  参考文献：
  名称：

  Toward the Development of a Cephalosporin-Based Dual-Release Prodrug for Use in ADEPT

  摘要：

  In previous work we have shown that a cephalosporin structure bearing an S-aminosulfenimine at the 7-position behaved as a beta-lactamase-dependent dual-release prodrug. Scission of the beta-lactam ring of such a structure led to the rapid loss of the sulfur-attached side chain moiety via an intramolecular displacement, while the T-group was lost via the well-established elimination process at that position. In the present work we report on an evaluation of the scope and limitations of exploiting the S-aminosulfenimine functionality to generate a cephalosporin-based prodrug incorporating two biologically active components. Starting from 7-ACA, a viable synthetic cycle was put in place that avoided formation of the Delta(2) isomer throughout and that allowed incorporation of aminoglutethimide at the 3'-position and of a tosyl S-aminosulfenimine at the 7-position. The direct incorporation of a biologically active sulfonamide (ethoxzolamide) or a sulfamate (coumate) at this latter position was not achieved as a result of the difficulty of generating the corresponding sulfur diimides. An indirect route for the formation of an S-aminosulfenimine was put in place, as was a general method of alkylation (Mitsunobu reaction) of the tosyl S-ammosulfenimine following its incorporation.

  DOI：

  10.1021/jo048970i

文献信息

• Miticidal, insecticidal, ovicidal and fungicidal
  申请人：E. I. Du Pont de Nemours and Company

  公开号：US04309425A1

  公开（公告）日：1982-01-05

  Sulfonamides, such as N-[N-(2-chloro-5-(trifluoromethyl)phenyl]-N-[2,4-dinitro-6-(trifluoromethy l)phenyl]aminothio]-N,4-dimethylbenzenesulfonamide, are useful for control of arthropod pests of plants and animals and fungus disease of plants.

  磺胺类化合物，例如N-[N-(2-氯-5-(三氟甲基)苯基]-N-[2,4-二硝基-6-(三氟甲基)苯基]氨基硫]-N,4-二甲基苯磺酰胺，可用于控制植物和动物的节肢动物害虫和植物真菌病。
• Non-staining vulcanized elastomeric composition and tires having sidewalls comprising said composition
  申请人：THE GOODYEAR TIRE & RUBBER COMPANY

  公开号：EP0240448A2

  公开（公告）日：1987-10-07

  A vulcanizable composition which comprises diene rubber, an EPDM that has been modified to crosslink with the diene rubber, and a polymeric antidegradant, while being substantially free of staining antidegradants. This composition has particular utility in the sidewalls of tires.

  一种可硫化的组合物，包括二烯橡胶、一种经改性可与二烯橡胶交联的三元乙丙橡胶和一种聚合物防降解剂，但基本上不含染色防降解剂。这种组合物特别适用于轮胎侧壁。
• Polymer alloy
  申请人：THE GOODYEAR TIRE & RUBBER COMPANY

  公开号：EP0324312A2

  公开（公告）日：1989-07-19

  The present invention reveals a polymer alloy which is comprised of (a) at least one highly unsaturated rubbery polymer which is covulcanized with at least one N-chlorothio-sulfonamide modified EPDM rubber and (b) at least one thermoplastic resin. A blend of polypropylene with nitrile rubber which has been cocured with an N-chlorothio-sulfonamide modified EPDM rubber is a representative example of such a polymer alloy.

  本发明揭示了一种聚合物合金，它由(a)至少一种高度不饱和橡胶聚合物与至少一种 N-氯硫磺酰胺改性三元乙丙橡胶共硫化和(b)至少一种热塑性树脂组成。聚丙烯与丁腈橡胶的混合物是此类聚合物合金的代表，该混合物已与 N-氯硫磺酰胺改性三元乙丙橡胶共硫化。
• N-halothiosulfonamide modified rubber products and process for preparing the same
  申请人：EXXON CHEMICAL PATENTS INC.

  公开号：EP0430529A2

  公开（公告）日：1991-06-05

  N-halothiosulfonamide-modified rubber products are provided. The modified rubber products are prepared by reaction of a rubber, such as a butyl rubber or a halogenated butyl rubber, with a N-halothiosulfonamide in the absence or in the presence of a catalyst.

  提供了 N-卤代硫磺酰胺改性橡胶制品。改性橡胶制品是通过橡胶（如丁基橡胶或卤化丁基橡胶）在无催化剂或有催化剂的情况下与 N-卤代硫磺酰胺反应制备的。
• N-halothiosulfonamide-modified non-rubbery thermoplastic polyolefins
  申请人：EXXON CHEMICAL PATENTS INC.

  公开号：EP0431788A2

  公开（公告）日：1991-06-12

  N-halothiosulfonamide-modified non-rubbery thermoplastic polyolefins are provided. The modified polyolefin products are prepared by reaction of a non-­rubbery thermoplastic polyolefin polymer with an N-halothiosulfonamide in the absence or, preferably, in the presence of a catalyst. The preferred catalyst for use in the preparation of these products are salts of weak acids of specified metals.

  提供了 N-卤代硫磺酰胺改性非橡胶热塑性聚烯烃。改性聚烯烃产品是在无催化剂或有催化剂的情况下，通过非橡胶热塑性聚烯烃聚合物与 N-卤代硫磺酰胺反应制备的。用于制备这些产品的催化剂最好是特定金属的弱酸盐。