1,3-二噻戊环-2-羧酸 | 5616-65-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二硫杂环戊烷
• 中文名称: 1,3-二噻戊环-2-羧酸
• 英文名称: 1,3-dithiolane-2-carboxylic acid
• 英文别名: [1,3]dithiolane-2-carboxylic acid；[1,3]Dithiolan-2-carbonsaeure；1.3-dithiolane-2-carboxylic acid
• CAS: 5616-65-9
• 化学式: C₄H₆O₂S₂
• mdl: MFCD16876613
• 分子量: 150.222
• InChiKey: DSOVOUOPKYLGID-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  8
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  87.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,3-二噻戊环-2-羧酸 在 1-氯-N,N,2-三甲基丙烯胺 作用下， 以 氘代氯仿 为溶剂， 以100%的产率得到1,3-二噻戊环-2-甲酰氯
  参考文献：
  名称：

  用卤素取代羟基的温和方法。1.范围和化学选择性

  摘要：

  由相应的异丁酰胺容易制备的α-氯胺，溴胺和碘烯胺已被发现是将多种醇或羧酸转化为相应卤化物的极佳试剂。产率高并且条件非常温和，因此允许存在敏感的官能团。试剂易于调节，因此可以选择性地对多羟基化分子进行单卤代反应。研究了反应的范围和化学选择性，并提出了反应机理。

  DOI：

  10.1016/j.tet.2015.11.060
• 作为产物：
  描述：

  1,3-二硫烷-2-甲酸乙酯 在 三丁基氧化锡 作用下， 以 甲苯 为溶剂， 反应 10.0h， 以52%的产率得到1,3-二噻戊环-2-羧酸
  参考文献：
  名称：

  Scope and Mechanism of Deprotection of Carboxylic Esters by Bis(tributyltin) Oxide

  摘要：

  Methyl and ethyl esters of aliphatic and aromatic carboxylic acids as well as benzyl carboxylates, thiol esters and double esters such as (pivaloyloxy)methyl carboxylates have been successfully cleaved with bis(tributyltin) oxide to give the free carboxylic acids in good yields. The reaction is carried out in aprotic solvents under essentially neutral conditions and thus this method can serve as an ideal procedure for the cleavages of esters with other functional groups and/or protecting groups acid and/or base sensitive. We demonstrated that the reaction displays a high level of chemoselectivity between methyl and ethyl esters versus tert-butyl esters and gamma-lactones. Bis(tributyltin) oxide is also a highly efficient reagent for the cleavage of acetates of primary and secondary alcohols and phenols. The limitations we found in the use of this reagent include the lack. of cleavage of esters sterically hindered around the carboxyl carbon and the carbinol group (i.e., esters of tertiary alcohols) and in carboxylic esters that contain a fluoroalkyl substituent. A resonable mechanistic explanation is discussed to account for the reaction pathway of the acyloxygen cleavage of(-)-(1R)-menthyl acetate.

  DOI：

  10.1021/jo00103a016

文献信息

• 4-substituted azetidinones as precursors to 2-substituted-3-carboxy
  申请人：American Cyanamid Company

  公开号：US05371215A1

  公开（公告）日：1994-12-06

  New 4-substituted azetidinones having the formulae I and II: ##STR1## wherein X is oxygen, sulfur or a moiety of the formula NR.sup.6 where R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5 and R.sup.6 are defined hereafter, which are intermediates for the preparation of carbapenem and carbacephem antibacterials and processes for producing such antibacterials through the utilization of an acid mediated ring closure reaction.

  具有以下结构式I和II的新4-取代氮杂环丁酮：其中X为氧、硫或具有结构式NR.sup.6的基团，其中R.sup.1、R.sup.2、R.sup.3、R.sup.4、R.sup.5和R.sup.6如下所定义，这些化合物是制备碳青霉烯和碳头霉素抗菌药物的中间体，并通过酸介导的环闭合反应制备此类抗菌药物的过程。
• Triazolinone Biphenylsulfonamide Derivatives as Orally Active Angiotensin II Antagonists with Potent AT1 Receptor Affinity and Enhanced AT2 Affinity
  作者：Wallace T. Ashton、Linda L. Chang、Kelly L. Flanagan、Steven M. Hutchins、Elizabeth M. Naylor、Prasun K. Chakravarty、Arthur A. Patchett、William J. Greenlee、Tsing-Bau Chen

  DOI：10.1021/jm00043a020

  日期：1994.8

  cycloalkylcarbonyl derivatives. Certain other acidic sulfonamides, such as sulfonylcarbamates and disulfimides also displayed high affinity for the AT1 receptor. In addition, AT2 binding for some of these compounds was increased by as much as 1000-fold over the corresponding tetrazole (e.g., AT2 IC50 17 nM for the tert-butyl sulfonylcarbamate 92). When evaluated for inhibition of the AII pressor response, the benchmark

  几个系列的2,4-二氢-2,4,5-三取代的3H-1,2,4-三唑-3-酮在联苯-4-基甲基的2'-位上被四唑的酸性磺酰胺取代制备N4链并作为血管紧张素II（AII）拮抗剂进行测试。三唑啉酮环上的优选取代基是在C5处的正丁基和在N2处的2-（三氟甲基）苯基。对于多种酰基磺酰胺，包括芳酰基，杂芳酰基和环烷基羰基衍生物，观察到AT1受体亚型的亚纳摩尔IC50值。某些其他酸性磺酰胺，如磺酰氨基甲酸酯和二硫化亚胺也对AT1受体表现出高亲和力。另外，这些化合物中某些化合物的AT2结合量比相应的四唑增加了1000倍（例如，叔丁基磺酰基氨基甲酸酯92的AT2 IC50 17 nM）。当评估抑制AII升压反应时，基准苯甲酰磺酰胺9（L-159,913）在几种物种中均有效，在有意识的恒河猴中优于氯沙坦（1a）。随后的几种类似物，包括2-氯苯甲酰基（18），（3-氯噻吩-2-基）羰基（51），（（S）-2,2
• Synthetic Equivalents Based on Weinreb Amide Functionality for Convenient Access to Monoprotected α-Diketones
  作者：Indrapal Aidhen、Sivaraman Balasubramaniam

  DOI：10.1055/s-2007-973882

  日期：2007.4

  A convenient new strategy for the synthesis of monoprotected α-diketones has been achieved. The strategy is based on the use of hitherto unreported N-methoxy- N-methyl-1,3-dithiolane-2-carboxamide and N-methoxy- N-methyl-1,3-dithiane-2-carboxamide as synthetic equivalent for an α-dicarbonyl unit with opposing polarity. Nucleophilic addition on the amide functionality followed by alkylation furnished

  已经实现了合成单保护α-二酮的便捷新策略。该策略基于使用迄今未报道的 N-甲氧基-N-甲基-1,3-二硫烷-2-甲酰胺和 N-甲氧基-N-甲基-1,3-二噻烷-2-甲酰胺作为合成等价物具有相反极性的α-二羰基单元。酰胺官能团上的亲核加成然后烷基化以中等至良好的产率提供目标单保护的α-二酮。
• Investigation of an onsite wastewater treatment system in sandy soil: Sorption and biodegradation of linear alkylbenzene sulfonate
  作者：Jon Doi、Kay H. Marks、Alvaro J. Decarvalho、Drew C. McAvoy、Allen M. Nielsen、Louis Kravetz、Manuel L. Cano

  DOI：10.1002/etc.5620211213

  日期：2002.12

  sulfonate (LAS) in a soil below a Florida, USA, septic system drainfield. Three distinct soil samples were collected from the septic system drainfield study site. These soils were used in laboratory sorption and biodegradation studies. Different concentrations of LAS were added, in radiolabeled and unlabeled forms, to a series of test vessels that contained upgradient groundwater and the soils collected from

  这项工作的目的是确定直链烷基苯磺酸盐 (LAS) 在美国佛罗里达州化粪池系统排水场下方土壤中的吸附和生物降解特性。从化粪池系统排水场研究地点收集了三个不同的土壤样本。这些土壤用于实验室吸附和生物降解研究。将放射性标记和未标记形式的不同浓度的 LAS 添加到一系列测试容器中，这些容器包含升级地下水和从研究地点收集的土壤。吸附测试旨在确定 LAS 在每个样品中地下水和土壤之间的分配。结果表明，吸附分布系数（Kd）从4.02下降到0.43 L/kg，最终生物降解速率（一级速率常数，k1）从2.17下降到0。08/d 随着距排水场的距离增加（垂直低于地面 [BGS] 0.7-1.2 m 和水平 0 至 6.1 m）。在 45 天或 59 天的测试期间，这三种土壤显示出 49.8% 至 83.4% 的 LAS 矿化（理论 CO2 的百分比）。这些结果表明，该系统中的地下土壤具有吸附和生物降解 LAS
• 3-(1,3-Dithian-2-yl)-4-cyclo-pentene-2-carboxylic acids, esters and
  申请人：Recherche et Industrie Therapeutiques (R.I.T.)

  公开号：US03947469A1

  公开（公告）日：1976-03-30

  The invention relates to the stereoisomers of novel cyclopentene derivatives and to the preparation thereof. The cyclopentene derivatives are obtained by cycloaddition reaction between cyclopentadiene and a mono-or bis-thioalkyl (or aryl) ketene and reaction between the obtained product and a nucleophile agent. The compounds of the invention are intermediate products valuable for the preparation of different compounds, among which compounds of the prostaglandin type.

  该发明涉及新型环戊烯衍生物的立体异构体以及其制备方法。环戊烯衍生物是通过环戊二烯和单酰基或双硫烷基（或芳基）酮烯之间的环加成反应以及所得产物与亲核试剂的反应来获得的。该发明的化合物是用于制备不同化合物的中间产物，其中包括前列腺素类化合物。