sulfinylcarbamic acid ethyl ester | 5659-92-7

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: sulfinylcarbamic acid ethyl ester
• 英文别名: N-sulfinyl urethane；Carbamic acid, sulfinyl-, ethyl ester；ethyl N-sulfinylcarbamate
• CAS: 5659-92-7
• 化学式: C₃H₅NO₃S
• 分子量: 135.144
• InChiKey: WWKLPECCKCCXBJ-UHFFFAOYSA-N

物化性质

• 沸点：
  30 °C(Press: 0.1 Torr)
• 密度：
  1.262 g/cm3

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  8
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  56.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  sulfinylcarbamic acid ethyl ester 在 吡啶 、 calcium chloride 作用下， 以85%的产率得到N,N'-bis(ethoxycarbonyl) sulfur diimide
  参考文献：
  名称：

  S-Aminosulfeniminopenicillins:  Multimode β-Lactamase Inhibitors and Template Structures for Penicillin-Based β-Lactamase Substrates as Prodrugs

  摘要：

  A series of novel penicillins, bearing an S-aminosulfenimine (R'(R ")NSN=) side chain at the 6-position, have been prepared by direct reaction of a penicillin eater with sulfur diimides. A set of these structures, with the thiazolidine-ring sulfur in the sulfide oxidation state, exhibited a pattern of reactivity not previously encountered in penicillin chemistry, viz., cleavage of the beta-lactam ring resulted in a rapid intramolecular displacement of the S-amino moiety as R'(R ")NH. This was found to be the exclusive reaction occurring consequent on cleavage of the p-lactam ring. The mechanism of this process was delineated in a detailed study in basic methanol. That a similar reactivity pattern held for a penicillin salt in aqueous solution was also verified. Thus the salt 5bm (R' = CH3, R " = p-CH3C6H4SO2) behaved as a moderate substrate for beta-lactamase type I from Bacillus cereus (k(cat)/K-m = 6.26 x 10(5) M-1 min(-1)). On enzyme-catalyzed hydrolysis of this compound, displacement of N-methyl-p-toluenesulfonamide (R'(R ")NH) was directly observed (H-1 NMR) and found to occur faster than displacement of this group from (intact) 5bm in aqueous buffer, by a factor of at least 600. These findings identified the potential of the S-aminosulfeniminopenicillin structure type to be developed as beta-lactamase substrates for use as site-specific-release prodrugs. A degree of enzyme inhibition was also observed with this set of thiazolidinering-sulfide structures with the most potent inhibitor having the most nucleofugic S-amino moiety p-ClC6H4SO2N(CH3), indicating that displacement of this group, at the enzyme active site, played a role in their mode of inhibition. Structures with the thiazolidine-ring sulfur in the sulfone oxidation state were considerably more potent as inhibitors, with the structure 5a(2) being the most active. As this compound bore the least nucleofugic S-amino moiety C2H5OC(O)NH, it indicated that the mode of inhibition of the sulfones was distinct from that of the thiazolidine-ring sulfides; it is probable that the sulfones reacted in a manner similar to that shown by sulbactam viz., rapid scission of the thiazolidine-sulfone ring after cleavage of the beta-lactam ring. Synergy of action was observed with 5a(2) at high concentration (78 mu g/mL) against Escherichia coli when combined 1:1 with penicillin G; no synergy was observed at low concentration (4 mu g/mL) when combined with pipericillin, indicating poor permeation characteristics.

  DOI：

  10.1021/jo970737f
• 作为产物：
  描述：

  diethyl N-chlorocarbonimidate 在 氯化亚砜 作用下， 生成 sulfinylcarbamic acid ethyl ester
  参考文献：
  名称：

  Hoerhold,H.-H.; Eibisch,H., Chemische Berichte, 1968, vol. 101, # 10, p. 3567 - 3578

  摘要：

  DOI：
• 作为试剂：
  描述：

  1,4-萘醌 在 吡啶 、 二氯化二硫 、 氯化亚砜 、 sulfinylcarbamic acid ethyl ester 、 二氯化硫 作用下， 以 苯 为溶剂， 反应 10.0h， 生成 naphtho<2,3-c><1,2,5>thiadiazole-4,9-dione
  参考文献：
  名称：

  Use of Thiazyl Chlorides, Alkyl Carbamates, and Thionyl Chloride To Fuse 1,2,5-Thiadiazoles to Quinones and To Oxidize, Chlorinate, and Aminate Them

  摘要：

  Thiazyl chlorides in a simple one-step procedure fuse 1,2,5-thiadiazole rings to quinones. So do alkyl carbamates mixed with excess thionyl chloride and pyridine. Evidence is put forward to support the hypothesis that NSCl or a related thiazyl derivative is the reactive species that brings about the transformations. Selenoyl chloride mixed with an alkyl carbamate, pyridine, and quinones similarly gives 1,2,5-selenodiazoloquinones. Thionyl chloride in pyridine chlorinates quinones and oxidizes hydroquinones. 2,3-Dichloro-1,4-quinones with S4N4 or. with alkyl N-sulfinylcarbamates give 1,2,5-thiadiazoloquinones. Quinones and their 2 3-dichloro derivatives with TsNSO in pyridine give betaine derivatives of 2,3-diaminoquinones, which pyrrolidine converts into 2-amino-3(tosylamino)quinones. A unified set of mechanisms is presented that accounts for these transformations.

  DOI：

  10.1021/jo00110a036

文献信息

• Neue 17-Spirosteroide, III. Synthese von Steroid-17-spiro-5′-(1′,2′,3′-oxathiazolidin)-2′-oxiden
  作者：Sándor Sólyom、Katalin Szilágyi、Lajos Toldy

  DOI：10.1002/jlac.198319830613

  日期：1983.6.15

  Aus den 17β-Hydroxy-17α-Hydroxy-17α-(methylaminomethyl)steroiden 1 wurden mit Thionylchlorid, N-Sulfinylamiden 3 und N,N′-Sulfinyldiaminen 6 die Steroid-17-spiro-5′-(1′,2′,3′-oxathiazolidin)-2′-oxide 2, eine neue Klasse des 17-Spirosteroide, hergestellt. Die neuen Spiroverbindungen entstehen als diastereomere Gemische. Je nach dem verwendeten Typ des Ringschlußreagenzes wurden verschiedene Diasteromeren-Verhältnisse

  从17β-羟基-17α-羟基17α-（甲基氨基甲基）甾体1与亚硫酰氯，N-亚磺酰胺3和N，N'-亚磺酰二胺6混合，甾体17-spiro-5'-（1'，2 '，3'-oxathiazolidine）-2'-oxide 2，这是一类新的17-螺类固醇。新的螺环化合物以非对映异构体混合物的形式出现。根据所使用的闭环试剂的类型，发现了不同的非对映异构体比率。借助1 H-NMR光谱确定异构体的结构。
• Steroid-spiro-oxathiazolidine derivatives and a process for the
  申请人：Richter Gedeon Vegyeszeti Gyar RT

  公开号：US04342754A1

  公开（公告）日：1982-08-03

  New steroid-spiro-oxathiazolidine derivatives pharmaceutical compositions containing the same, and to a process for the preparation thereof are disclosed. The new compounds have antimineral corticoide effects and have the following formula (I), ##STR1## wherein R.sub.1 is a C.sub.1-3 alkyl or a C.sub.2-4 alkenyl group, and Z is a group of the formulae (II) to (VI), ##STR2## wherein R.sub.2 is methyl or ethyl, R.sub.3 is hydrogen or methyl R.sub.4 is hydrogen, a C.sub.1-3 alkyl group, a di-(C.sub.1-4 alkyl)-amino-C.sub.1-4 alkyl group, a C.sub.2-4 alkylcarbonyl group, a C.sub.2-4 alkoxycarbonyl group or a C.sub.3-6 carboxyalkylcarbonyl group, and the dotted lines may represent additional valence bonds, with the proviso that if Z is a group of the formula (VI), a double bond exists between the carbon atoms in positions 4 and 5 or 5 and 6, and if R.sub.4 is a di-(C.sub.1-4 alkyl)-amino-C.sub.1-4 alkyl group or a C.sub.3-6 carboxyalkylcarbonyl group, the compounds may also be formed as their salts.

  本文揭示了新的类固醇-螺-氧噻唑啉衍生物药物组合物及其制备方法。这些新化合物具有抗矿物质皮质激素作用，其化学式如下（I）：##STR1## 其中，R.sub.1是C.sub.1-3烷基或C.sub.2-4烯基基团，而Z是式（II）至（VI）的基团：##STR2## 其中，R.sub.2是甲基或乙基，R.sub.3是氢或甲基，R.sub.4是氢、C.sub.1-3烷基、二（C.sub.1-4烷基）-氨基-C.sub.1-4烷基、C.sub.2-4烷基羰基、C.sub.2-4烷氧基羰基或C.sub.3-6羧基烷基羰基，虚线可以表示额外的价键。但如果Z是式（VI）的基团，则碳4和5或5和6位置之间存在双键。如果R.sub.4是二（C.sub.1-4烷基）-氨基-C.sub.1-4烷基或C.sub.3-6羧基烷基羰基，则这些化合物也可以形成它们的盐。
• Bussas, Reinhard; Kresze, Guenter, Liebigs Annalen der Chemie, 1982, # 3, p. 545 - 563
  作者：Bussas, Reinhard、Kresze, Guenter

  DOI：——

  日期：——
• Alkoxycarbonyl-isocyanate durch thermolytische spaltung von n-alkoxycarbonyl-substituierten schwefelimiden
  作者：H.-J. Niclas、D. Habisch、D. Martin

  DOI：10.1016/s0040-4020(01)93749-4

  日期：1979.1
• 5,6-Dihydro-2<i>H</i>-1,2,3,6-thiatriazin-1-oxide durch Cycloadditionen von Azoalkenen an<i>N</i>-Sulfinyl-Verbindungen¹
  作者：Sven SOMMER

  DOI：10.1055/s-1977-24368

  日期：——