2-[3',4',5'-trimethoxyphenyl]-1,3-dithiolane | 72553-20-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-[3',4',5'-trimethoxyphenyl]-1,3-dithiolane
• 英文别名: 2-(3,4,5-Trimethoxyphenyl)-1,3-dithiolane
• CAS: 72553-20-9
• 化学式: C₁₂H₁₆O₃S₂
• 分子量: 272.389
• InChiKey: XZRSIKWZNNXTCJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  78.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-[3',4',5'-trimethoxyphenyl]-1,3-dithiolane 在 β-环糊精 、 2-碘酰基苯甲酸 作用下， 以 丙酮 为溶剂， 反应 2.5h， 以87%的产率得到3,4,5-三甲氧基苯甲醛
  参考文献：
  名称：

  Krishnaveni, N. Srilakshmi; Surendra, K.; Nageswar, Y. V. D., Synthesis, 2003, # 15, p. 2295 - 2297

  摘要：

  DOI：
• 作为产物：
  描述：

  (3,4,5-Trimethoxyphenyl)methylene diacetate 、 1,2-乙二硫醇 在 sulfonated polyanthracene 作用下， 反应 0.12h， 以97%的产率得到2-[3',4',5'-trimethoxyphenyl]-1,3-dithiolane
  参考文献：
  名称：

  Sulfonated polyanthracene-catalyzed highly efficient and chemoselective thioacetalization of carbonyl compounds and transthioacetalization of acetals and acylals

  摘要：

  A straightforward and highly efficient procedure for the thioacetalization of a variety of aldehydes and transthioacetalization of acylals and acetals in good to excellent yields using catalytic amounts of sulfonated polyanthracene (S-PAT) is reported. The reactions were carried out in the presence of 1,2-ethanedithiol and 1,3-propanedithiole at room temperature under solvent-free conditions. Thioacetals were also prepared by the reaction of aromatic ketone and dithiole using S-PAT under reflux conditions in H2O as green solvent.

  DOI：

  10.1080/17415993.2014.958751

文献信息

• An Efficient Method for Chemoselective Thioacetalization of Aldehydes in the Presence of a Catalytic Amount of Acidic Ionic Liquid under Solvent-Free Conditions
  作者：Abdol Hajipour、Ghobad Azizi、Arnold Ruoho

  DOI：10.1055/s-0029-1217550

  日期：2009.7

  A water-stable Brønsted acidic ionic liquid with an alkane sulfonic acid group was synthesized. This ionic liquid catalyzed the thioacetalization reaction smoothly to afford 1,3-dithianes in excellent yield and less time. In this article we describe a mild and chemoselective thioacetalization procedure for the protection of various aldehydes in the presence of catalytic amount of ionic liquid (2 mol%).

  合成了一种具有烷基磺酸基团的水稳定型Brønsted酸性离子液体。该离子液体催化硫缩醛化反应顺利进行，以极佳的产率和较短的时间得到1,3-二硫杂环戊烷。本文描述了一种在离子液体（2摩尔%）催化下缓和且化学选择性保护各种醛的硫缩醛化方法。
• Silica-Supported Perchloric Acid (HClO₄-SiO₂): A Versatile Catalyst for Tetrahydropyranylation, Oxathioacetalization and Thioacetalization
  作者：Abu Khan、Tasneem Parvin、Lokman Choudhury

  DOI：10.1055/s-2006-942465

  日期：2006.8

  A simple and convenient synthetic protocol for the protection of hydroxyl group as tetrahydropyranyl ether as well as carbonyl functionality as oxathioacetal and thioacetal has been achieved using a catalytic amount of silica-supported perchloric acid under solvent-free conditions. This protocol has many advantages compared to currently available methodologies in terms of simplicity, yield, reaction

  在无溶剂条件下使用催化量的二氧化硅负载的高氯酸实现了一种简单方便的合成方案，用于保护作为四氢吡喃醚的羟基以及作为草硫缩醛和硫缩醛的羰基官能团。与目前可用的方法相比，该协议在简单性、产率、反应时间、催化剂的可重复使用性和经济可行性方面具有许多优势。
• Indium tribromide-catalyzed chemoselective dithioacetalization of aldehydes in non-aqueous and aqueous media
  作者：Marco Antonio Ceschi、Luciana de Araujo Felix、Clovis Peppe

  DOI：10.1016/s0040-4039(00)01741-x

  日期：2000.12

  Indium tribromide efficiently catalyzes the chemoselective dithioacetalization of aldehydes in the presence of ketones in dichloromethane. The catalyst is also active in water, which can be reused, in the same pot, for several times without any decrease in the yield of reaction.

  在二氯甲烷中有酮存在下，三溴化铟可有效催化醛的化学选择性二硫缩醛化。该催化剂在水中也具有活性，可以在同一罐中重复使用几次，而不会降低反应的产率。
• Indium-catalyzed inter- and intramolecular dithianyl–alkyne metathesis reactions
  作者：Xi Chen、Rui-peng Li、Peng Long、Yuxi Tang、Jia Li、Shouchu Tang

  DOI：10.1039/d3cc05622h

  日期：——

  Herein, we reported an efficient indium catalyzed dithianyl–alkyne metathesis (DAM) reaction. This strategy allows for the formation of a new C–C double bond and valuable C–S bonds during the metathesis event, and was successfully applied to the synthesis of diverse vinyl dithianyl substituted organic molecules.

  在此，我们报道了一种高效的铟催化二噻烷基-炔复分解（ DAM ）反应。该策略允许在复分解过程中形成新的C-C双键和有价值的C-S键，并成功应用于多种乙烯基二噻烷基取代的有机分子的合成。
• A convenient oxidative demasking of 1,3-dithiolanes and dithianes to carbonyl compounds with TBHP
  作者：Nivrutti B Barhate、Popat D Shinde、Vishal A Mahajan、Radhika D Wakharkar

  DOI：10.1016/s0040-4039(02)01210-8

  日期：2002.8

  Regeneration of carbonyl compounds from their 1,3-dithiolanes and dithianes was achieved using tert-butyl hydroperoxide (TBHP, aq. 70%) in high yields. Thus, an efficient, economic and experimentally simple protocol for dethioacetalization has been demonstrated. (C) 2002 Elsevier Science Ltd. All rights reserved.