2-(naphthalene-1-yl)-1,3-oxathiolane

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-(naphthalene-1-yl)-1,3-oxathiolane
• 英文别名: 2-Naphthalen-1-yl-1,3-oxathiolane
• 化学式: C₁₃H₁₂OS
• 分子量: 216.304
• InChiKey: WXCGOSDQQISKPB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  34.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1-萘甲醛 、 2-巯基乙醇 在 PPA 、 silica gel 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 0.5h， 以100%的产率得到2-(naphthalene-1-yl)-1,3-oxathiolane
  参考文献：
  名称：

  Silica Gel-Supported Polyphosphoric Acid (PPA/SiO₂) as an Efficient and Reusable Catalyst for Conversion of Carbonyl Compounds into Oxathioacetals and Dithioacetals

  摘要：

  开发了一种简单高效的方法，通过使用负载在硅胶上的多磷酸（PPA/SiO2）作为酸催化剂，将羰基化合物转化为氧硫酯和二硫酯。PPA/SiO2可以轻松从反应混合物中回收，并且在重复使用时没有催化活性下降。

  DOI：

  10.1055/s-2004-832812

文献信息

• Silica Gel-Supported Polyphosphoric Acid (PPA/SiO₂) as an Efficient and Reusable Catalyst for Conversion of Carbonyl Compounds into Oxathioacetals and Dithioacetals
  作者：Tadashi Aoyama、Toshio Takido、Mitsuo Kodomari

  DOI：10.1055/s-2004-832812

  日期：——

  A simple and efficient method for the conversion of carbonyl compounds to oxathioacetals and dithioacetals by using polyphosphoric acid supported on silica gel (PPA/SiO2) as an acid catalyst have been developed. PPA/SiO2 is easily recovered from the reaction mixture and reused without a decrease in catalytic ­activity.

  开发了一种简单高效的方法，通过使用负载在硅胶上的多磷酸（PPA/SiO2）作为酸催化剂，将羰基化合物转化为氧硫酯和二硫酯。PPA/SiO2可以轻松从反应混合物中回收，并且在重复使用时没有催化活性下降。
• CERIC AMMONIUM NITRATE AS A CONVENIENT CATALYST FOR PROTECTION OF CARBONYL COMPOUNDS AS 1,3-OXATHIANES
  作者：Gourhari Maiti、Subhas Chandra Roy

  DOI：10.1081/scc-120005996

  日期：2002.1

  method for the protection of carbonyl compounds as 1,3-oxathianes has been established by the catalytic use of ceric ammonium nitrate at ambient temperature. While different types of aryl and alkyl ketones and aldehydes were protected smoothly, cyclic aryl ketones and diaryl ketones remained unaffected under the reaction conditions.

  摘要 通过在环境温度下催化使用硝酸铈铵，建立了一种温和有效的保护羰基化合物 1,3-氧杂环丙烷的方法。虽然不同类型的芳基和烷基酮和醛被顺利保护，但环芳基酮和二芳基酮在反应条件下不受影响。
• Tantalum(V) Chloride–Silica Gel: An Efficient Catalyst for Conversion of Carbonyl Compounds to 1,3‐Oxathiolanes
  作者：S. Chandrasekhar、S. Jaya Prakash、T. Shyamsunder、T. Ramachandar

  DOI：10.1080/00397910500282588

  日期：2005.12.1

  A variety of carbonyl compounds can be easily converted to the corresponding 1,3-oxathiolanes in the presence of a catalytic amount of tantalum(V) chloride [TaCl5] on silica gel in dichloromethane. Mild reaction conditions, efficiency, high yields, operational simplicity, and only 2.5 mol% of TaCl5 catalyst are some of the major advantages of the procedure.
• 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.
• 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。