2-methyl-2-methoxycarbonylmethyl-1,3-oxathiolane | 80563-95-7

• 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-methoxycarbonylmethyl-1,3-oxathiolane
• 英文别名: 1,3-Oxathiolane-2-acetic acid, 2-methyl-, methyl ester；methyl 2-(2-methyl-1,3-oxathiolan-2-yl)acetate
• CAS: 80563-95-7
• 化学式: C₇H₁₂O₃S
• 分子量: 176.236
• InChiKey: IPBJFXHDCTZHTJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 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-2-methoxycarbonylmethyl-1,3-oxathiolane 在 sodium hydroxide 、 磺酰氯 、 三乙胺 作用下， 以 乙醇 为溶剂， 反应 5.0h， 生成 2-甲基-5,6-二氢-1,4-氧硫杂环己二烯-3-甲酸
  参考文献：
  名称：

  Nevalainen, Vesa; Pohjala, Esko, Journal of Chemical Research, Miniprint, 1988, # 6, p. 1401 - 1421

  摘要：

  DOI：
• 作为产物：
  描述：

  乙酰乙酸甲酯 、 2-巯基乙醇 在 碘 作用下， 反应 0.07h， 以80%的产率得到2-methyl-2-methoxycarbonylmethyl-1,3-oxathiolane
  参考文献：
  名称：

  Microwave-mediated Efficient Protection of Carbonyl Compounds as 1,3-Oxathiolanes in the Presence of Iodine under Solvent Free Condition

  摘要：

  报道了一种温和、高效且无溶剂的协议，使用2-巯基乙醇在催化量的单质碘存在下，将醛和酮转化为相应的1,3-氧噻烷。

  DOI：

  10.1246/cl.2006.542

文献信息

• Indium Trifluoromethanesulfonate as a Mild and Chemoselective Catalyst for the Conversion of Carbonyl Compounds into 1,3-Oxathiolanes
  作者：Tsuneo Sato、Kiyoshi Kazahaya、Nao Hamada、Shinya Ito

  DOI：10.1055/s-2002-33541

  日期：——

  An efficient method for the preparation of 1,3-oxathiolanes from aldehydes and ketones with 2-mercaptoethanol in the presence of a catalytic amount of indium trifluoromethanesulfonate is reported.

  报道了在催化量的三氟甲磺酸铟存在下，用 2-巯基乙醇从醛和酮制备 1,3-氧杂硫杂环戊烷的有效方法。
• 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。
• Selective Catalytic Transesterification, Transthiolesterification, and Protection of Carbonyl Compounds over Natural Kaolinitic Clay
  作者：Datta E. Ponde、Vishnu H. Deshpande、Vivek J. Bulbule、Arumugam Sudalai、Anil S.Gajare

  DOI：10.1021/jo971404l

  日期：1998.2.1

  Transesterification and transthiolesterification of beta-keto esters with variety of alcohols and thiols and selective protection of carbonyl functions with various protecting groups catalyzed by natural kaolinitic clay are described. The clay has been found to be an efficient catalyst in transesterifying long chain alcohols, unsaturated alcohols, and phenols to give their corresponding beta-keto esters in high yields. For the first time, transthiolesterification of beta-keto esters with a variety of thiols has been achieved under catalytic conditions. Clay also catalyzes selective transesterification of beta-keto esters by primary alcohols in the presence of secondary and tertiary alcohols giving corresponding beta-keto esters. A systematic study involving the reactivity of different nucleophiles (alcohols, amines, and thiols) toward beta-keto esters is also described. Sterically hindered carbonyl groups as well as alpha,beta-unsaturated carbonyl groups underwent protection without the deconjugation of the double bond. Chemoselective protection of aldehydes in the presence of ketones has also been achieved over natural kaolinitic clay.
• Synthesis of dihydro-1,4-oxathiins by rearrangement of 1,3-oxathiolane sulfoxides
  作者：Wha Suk Lee、Hoh Gyu Hahn、Kee Dal Nam

  DOI：10.1021/jo00364a033

  日期：1986.7
• Synthesis of dihydro-1,4-oxathiins by action of chlorine on 1,3-oxathiolanes
  作者：Wha Suk Lee、Oee Sook Park、Joong Kwon Choi、Kee Dal Nam

  DOI：10.1021/jo00233a012

  日期：1987.11