2-methyl-1,3-oxathiolane-2-acetic acid ethyl ester | 33868-62-1

• 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-1,3-oxathiolane-2-acetic acid ethyl ester
• 英文别名: ethyl2-(2-methyl-1,3-oxathiolan-2-yl)acetate；(2-methyl-[1,3]oxathiolan-2-yl)-acetic acid ethyl ester；(2-Methyl-[1,3]oxathiolan-2-yl)-essigsaeure-aethylester；ethyl 2-(2-methyl-1,3-oxathiolan-2-yl)acetate
• CAS: 33868-62-1
• 化学式: C₈H₁₄O₃S
• 分子量: 190.263
• InChiKey: GJRZXAUPJGXYBA-UHFFFAOYSA-N

物化性质

• 沸点：
  258.2±25.0 °C(Predicted)
• 密度：
  1.107±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  60.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-methyl-1,3-oxathiolane-2-acetic acid ethyl ester 、 氯 、 三乙胺 、 二氯甲烷 以85%的产率得到
  参考文献：
  名称：

  LEE, WHA, S.

  摘要：

  DOI：
• 作为产物：
  描述：

  乙酰乙酸乙酯 、 2-巯基乙醇 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 以65%的产率得到2-methyl-1,3-oxathiolane-2-acetic acid ethyl ester
  参考文献：
  名称：

  N-溴代琥珀酰亚胺对羰基化合物的氧硫代乙缩醛化，硫代缩醛化和反硫代缩醛化：选择性和范围

  摘要：

  使用N-溴代琥珀酰亚胺作为催化剂，已经以高收率实现了羰基化合物的有效的氧代硫代缩醛化，硫代缩醛化和反硫代缩醛化。

  DOI：

  10.1016/s0040-4039(02)01610-6

文献信息

• Blue LED-Promoted Oxathiacetalization of Aldehydes and Ketones
  作者：You-Chen Liu、Daggula Mallikarjuna Reddy、Xin-An Chen、Yi-Chen Shieh、Chin-Fa Lee

  DOI：10.1002/ejoc.202000218

  日期：2020.5.10

  A visible‐light‐promoted oxathiacetalization of aldehydes and ketones with 2‐mercaptoethanol and 3‐mercaptopropan‐1‐ol in the presence of eosin Y as catalyst is described leading to the formation of 1,3‐oxathiolanes and 1,3‐oxathianes at ambient temperature and under metal‐free conditions. The solvent is playing vital role in the protection of carbonyl compounds with mercaptoalcohol.

  描述了在曙红Y的催化下，使用2-巯基乙醇和3-巯基丙烷-1-醇在可见光条件下促进醛和酮的乙二醛乙醛缩醛化反应，从而导致1,3-氧杂硫杂环戊烷和1,3-氧杂蒽环的形成环境温度和无金属条件下。溶剂在用巯基醇保护羰基化合物中起着至关重要的作用。
• The Reaction of 2-Ethoxy-1,3-oxathiolane with Carbonyl Compounds in the Presence of ZnCl₂or HgCl₂
  作者：Shigeo Tanimoto、Shigeo Jo、Toyonari Sugimoto、Masaya Okano

  DOI：10.1246/bcsj.54.3237

  日期：1981.10

  In the reaction of 2-ethoxy-1,3-oxathiolane with carbonyl compounds in the presence of ZnCl2 or HgCl2, it has been found that only the breaking of the endocyclic bond (C–O or C–S bond) occurs, while the breaking of the exocyclic C–O bond to give the 1,3-oxathiolan-2-ium ion is unfavorable. This behavior is different from that of 2-ethoxy-1,3-dithiolane, in which the breaking of the endocyclic C–S bond

  在 ZnCl2 或 HgCl2 存在下，2-乙氧基-1,3-氧杂硫杂环戊烷与羰基化合物反应，发现仅发生内环键（C-O 或 C-S 键）断裂，而环外 C-O 键断裂产生 1,3-oxathiolan-2-ium 离子是不利的。这种行为不同于 2-乙氧基-1,3-二硫戊环，其中环内 C-S 键通过 HgCl2 和外环 C-O 键发生断裂，通过 ZnCl2。
• Studies in Organic Sulfur Compounds. VI.¹ Cyclic Ethylene and Trimethylene Hemithioketals
  作者：Carl Djerassi、Marvin Gorman

  DOI：10.1021/ja01111a029

  日期：1953.8
• Facile protection of carbonyl compounds as oxathiolanes and transoxathioacetalization of oxyacetals promoted by iron(III) trifluoroacetate or trifluoromethanesulfonate as chemoselective and recyclable catalysts
  作者：Hadi Adibi、Hadi Jafari

  DOI：10.1016/j.jfluchem.2007.04.002

  日期：2007.6

  Oxathioacetalization of carbonyl compounds and transoxathioacetalization of O,O-acetals/ketals are reported under nearly neutral conditions promoted by iron(III) trifluoroacetate [Fe(CF3CO2)(3)] or trifluoromethanesulfonate [Fe(CF3SO3)(3)] as recyclable and highly efficient Lewis acid catalysts. (c) 2007 Elsevier B.V. All rights reserved.
• Electron impact induced fragmentations of some 2,2-disubstituted 1,3-oxathiolanes
  作者：Pirjo Vainiotalo、Vesa Nevalainen

  DOI：10.1002/oms.1210210804

  日期：1986.8

  AbstractThe electron impact induced fragmentations of nine 2,2‐disubstituted 1,3‐oxathiolanes have been studied by means of exact mass measurement and metastable ion analysis. The ring cleavage almost always takes place so that the C(2)S and C(5)O bonds are broken, leading to the most stable products. The nature of the substituents determines the primary fragmentations of molecular ions. Ring cleavage is important only if both substituents are alkyl groups or if the carbon attaching to the ring has an alkyl character. The loss of the substituent becomes the most favourable process if it is attached to the ring through the electron‐deficient carbon atom.