2-methyl-2-phenyl-1,3-oxathiolan-5-one | 797799-58-7

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫代缩醛
• 英文名称: 2-methyl-2-phenyl-1,3-oxathiolan-5-one
• CAS: 797799-58-7
• 化学式: C₁₀H₁₀O₂S
• 分子量: 194.254
• InChiKey: QUSUPJHYLRUCHR-UHFFFAOYSA-N

物化性质

• 沸点：
  96-99 °C
• 密度：
  1.226±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  51.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-methyl-2-phenyl-1,3-oxathiolan-5-one 生成 2,2’-((1-phenylethane-1,1-diyl)bis(sulfanediyl))diacetic acid
  参考文献：
  名称：

  Holmberg, Arkiv foer Kemi, 1950, vol. 2, p. 567,572

  摘要：

  DOI：
• 作为产物：
  描述：

  2,2’-((1-phenylethane-1,1-diyl)bis(sulfanediyl))diacetic acid 生成 2-methyl-2-phenyl-1,3-oxathiolan-5-one
  参考文献：
  名称：

  Holmberg, Arkiv foer Kemi, 1950, vol. 2, p. 567,572

  摘要：

  DOI：

文献信息

• An unprecedented synthesis of γ-lactams via mercaptoacetylation of aziridines in water
  作者：Vijai K. Rai、Prashant Kumar Rai、Swati Bajaj、Anil Kumar

  DOI：10.1039/c0gc00899k

  日期：——

  A highly green and expeditious route to α-mercapto-γ-lactams from masked mercapto acids viz. 2-phenyl-2-methyl-1,3-oxathiolan-5-ones, and tosyl aziridines in an excellent yield (82–93%) is reported. The synthetic protocol involves regioselective opening of the terminal aziridine ring and mercaptoacetylative cyclisation cascades in a one-pot procedure wherein water acts as both a catalyst as well as a solvent. These reactions were carried out in aqueous media as well as under solvent-free conditions, however, under solvent-free conditions, lower yields are obtained.

  报道了一种从掩蔽巯基酸（即2-苯基-2-甲基-1,3-氧硫杂环戊烷-5-酮）和甲苯磺酰基氮杂环丙烷高效合成高度绿色、快捷的α-巯基-γ-内酰胺（产率为82-93%）的路线。合成方案涉及区域选择性的末端氮杂环丙烷环的开启和巯基乙酰化环化级联反应，采用一锅法操作，其中水既作为催化剂又作为溶剂。这些反应在水中进行或无溶剂条件下进行，但在无溶剂条件下，产率较低。
• Masked mercapto acid-driven MCR in task-specific ionic liquid: a new sterocontrolled entry into bicyclic 1,3-thiazines
  作者：Vijai K. Rai、Prashant Kumar Rai、Yogita Thakur

  DOI：10.1016/j.tetlet.2013.09.068

  日期：2013.11

  reaction for the synthesis of thiosugar-annulated 1,3-thiazines is reported. The envisaged synthetic strategy involves the reaction of d-glucose/d-xylose and 2-methyl-2-phenyl-1,3-oxathiolan-5-one with AcONH4/RNH2 in task specific ionic liquid (TSIL), [bmim]SCN which afforded thiosugar annulated 1,3-thiazines in excellent yields (83–93%). The reaction is effected via ionic liquid promoted Michael addition

  据报道，用于合成硫糖修饰的1，3-噻嗪的空前的多组分反应。设想的合成策略涉及任务特定离子液体（TSIL）中d-葡萄糖/ d-木糖和2-甲基-2-苯基-1,3-氧杂噻喃-5-酮与AcONH 4 / RNH 2的反应，[bmim ] SCN以优异的收率（83–93％）提供了硫糖使1，3-噻嗪环化。该反应通过一锅法中通过离子液体促进的迈克尔加成，然后巯基乙酰化环转化而进行，并且该离子液体可以容易地循环使用[bmim] OH，而不会损失任何效率，并且可以用于合成[ bmim] SCN，从而可以回收TSIL以便进一步使用。
• First iodine/IL-catalyzed carbohydrate activation as aldehyde equivalent for [C+2C+N] construction of β-lactam ring
  作者：Vijai K. Rai、Bhaskar Sharma、Vidya R. Sharoff、Ankita Rai

  DOI：10.1016/j.tetlet.2016.06.017

  日期：2016.7

  annulated β-lactams in excellent yield (86–94%) and high cis diastereoselectivity (96–99%). The envisaged method involves reaction of unprotected d-glucose/d-xylose as 1C, masked amino/-mercapto acid as 2C, and aromatic amines as N source in the present three-component synthesis. The reaction is effected via intramolecular aza-Michael addition followed by amino/-mercaptoacetylative cyclization in a one-pot

  我们公开了一种高效的分子I 2 / [bmim] OH催化的碳水化合物活化（醛当量），可合成亚氨基/硫糖糖环化的β-内酰胺，产率高（86-94％），顺式非对映选择性高（96-99％） 。设想的方法涉及未保护的d-葡萄糖/ d的反应在本三组分合成中，以-木糖为1C，以掩蔽的氨基/巯基酸为2C，以芳香胺为氮源。该反应通过分子内的氮杂-迈克尔加成反应，然后以一锅法进行氨基/巯基乙酰化环化反应来进行。用于β-内酰胺合成的已开发方法具有操作简单，环境反应条件和离子液体[bmim] OH易于回收再利用的优点，而不会降低效率。
• Peculiar reaction behavior of 1,3-oxathiolan-5-one toward various reagents: Molecular modeling studies and in vitro antioxidant and cytotoxicity evaluation
  作者：Wafaa S. Hamama、Mona E. Ibrahim、Eslam A. Ghaith、Hanafi H. Zoorob

  DOI：10.1080/00397911.2016.1276190

  日期：2017.3.19

  ABSTRACT Chemical reactivity of 2-methyl-2-phenyl-1,3-oxathiolan-5-one (1) toward various reagents such as hydroxyaldehyde, ketone, α,β unsaturated carbonyl compounds, heterocyclic amine, hydrazine, and hydrazide to give unpredicative opened and fused heterocyclic systems was investigated. Moreover, treatment of compound 1 with bromoester to afford the respective fused system, 2-methyl-2-phenylfuro[3,2-d][1

  摘要 2-methyl-2-phenyl-1,3-oxathiolan-5-one (1) 对各种试剂的化学反应性，如羟基醛、酮、α,β 不饱和羰基化合物、杂环胺、肼和酰肼，给出不可预测的研究了开环和稠合杂环系统。此外，用溴酯处理化合物1以提供各自的稠合系统2-甲基-2-苯基呋喃[3,2-d][1,3]氧硫醇-5(6H)-一(6)。此外，1H-1H核overhauser效应光谱被用于完全确认化合物19。此外，讨论了密度泛函理论模型研究结果，并评估了所有新合成的化合物作为抗氧化剂和抗肝细胞癌细胞系的细胞毒性试验. 图形概要
• One-pot <i>cis</i>-selective route to sugar-fused thiazines via a masking–unmasking strategy in basic ionic liquid
  作者：Vijai K. Rai、Rahul K. Kosta

  DOI：10.1139/cjc-2016-0155

  日期：2016.10

  A novel sequential Knoevenagel condensation, thia-Michael, and amino/mercaptoacetylative ring transformation reaction cascade for cis-selective synthesis of sugar-fused 1,3-thiazine is reported. The expeditious one-pot multicomponent annulation was performed using masked amino acid viz. 2-phenyl-1,3-oxazol-5-one or masked mercaptoacid viz. 2-methyl-2-phenyl-1,3-oxathiolan-5-one, d-xylose/d-glucose, and N-aryldithiocarbamic acid in ionic liquid [bmim]OH. The acetophenone obtained as a by-product and [bmim]OH itself could be easily recycled for further use without loss of efficiency. The envisaged method is operationally simple, high yielding, and excellent diastereoselective in favor of the cis-isomer of fused thiazines.

  报道了一种新颖的顺序Knoevenagel缩合、硫醇Michael反应和氨基/巯基乙酰化环转化反应级联，用于选择性合成糖融合的1,3-噻嗪的顺式异构体。快速的一锅多组分环化反应使用掩蔽氨基酸即2-苯基-1,3-噁唑-5-酮或掩蔽巯基酸即2-甲基-2-苯基-1,3-噁硫杂环戊烷-5-酮，d-木糖/d-葡萄糖和N-芳基二硫代氨基甲酸盐在离子液体[bmim]OH中进行。产生的苯乙酮作为副产物和[bmim]OH本身可以轻松回收再利用，而不会损失效率。所设想的方法操作简单，产率高，并对于融合噻嗪的顺式异构体具有出色的对映选择性。