benzaldehyde didodecyldithioacetal

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: benzaldehyde didodecyldithioacetal
• 英文别名: Bis(dodecylsulfanyl)methylbenzene
• 化学式: C₃₁H₅₆S₂
• 分子量: 492.918
• InChiKey: KKZRJQUSKHOTMO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  14.3
• 重原子数：
  33
• 可旋转键数：
  25
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  50.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  benzaldehyde didodecyldithioacetal 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 1.0h， 以73%的产率得到2-Dodecylsulfanyl-1,2-diphenylethanone
  参考文献：
  名称：

  Pot-Economy Autooxidative Condensation of 2-Aryl-2-lithio-1,3-dithianes

  摘要：

  The autoxidative condensation of 2-aryl-2-lithio-1,3-dithianes is here reported. Treatment of 2-aryl-1,3-dithianes with n-BuLi in the absence of any electrophile leads to condensation of three molecules of 1,3-dithianes and formation of highly functionalized α-thioether ketones orthothioesters in 51-89% yields upon air exposure. The method was further expanded to benzaldehyde dithioacetals, affording corresponding orthothioesters and α-thioether ketones in 48-97% yields. The experimental results combined with density functional theory studies support a mechanism triggered by the autoxidation of 2-aryl-2-lithio-1,3-dithianes to yield a highly reactive thioester that undergoes condensation with two other molecules of 2-aryl-2-lithio-1,3-dithiane.

  DOI：

  10.1021/acs.joc.7b02896
• 作为产物：
  描述：

  苯甲醛 、 十二硫醇 在 草酸 作用下， 以 硝基甲烷 为溶剂， 反应 7.0h， 以86%的产率得到benzaldehyde didodecyldithioacetal
  参考文献：
  名称：

  草酸促进羰基化合物或缩醛制备二硫缩醛

  摘要：

  这封信描述了草酸促进从羰基化合物和硫醇合成二硫缩醛。缩醛也可通过在类似条件下与硫醇反应转化为二硫缩醛...

  DOI：

  10.1246/cl.2007.104

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。
• Direct Synthesis of Unsymmetrical Dithioacetals
  作者：Sabine Bognar、Manuel Gemmeren

  DOI：10.1002/chem.202004835

  日期：2021.3.12

  only discuss symmetrical dithioacetals. Examples of mixed dithioacetals are scarce and no general method for the selective synthesis of these compounds exists. Herein, a synthetically simple general one‐step protocol was developed for the synthesis of a broad range of unsymmetrical dithioacetals consisting of one aromatic and one aliphatic thiol moiety from the corresponding aldehyde/thiol mixture. The

  二硫缩醛是合成有机化学中经常使用的基序，近来作为结构基序出现在有前景的抗植物病原体抗病毒剂中的关注日益增加。但是，大多数现有报告仅讨论对称的二硫缩醛。混合的二硫缩醛的例子很少，并且不存在用于选择性合成这些化合物的通用方法。本文中，开发了一种合成简单的通用单步操作规程，用于从相应的醛/硫醇混合物中合成范围广泛的不对称二硫缩醛，该不对称二硫缩醛由一个芳族基团和一个脂肪族硫醇基组成。混合小号，小号乙缩醛的收率很高，并且可以容忍各种官能团。动力学控制实现了对不对称二硫缩醛的出色选择性。
• Visible‐Light Photoredox‐Catalyzed Thioacetalization of Aldehydes Under Metal‐Free and Solvent‐Free Conditions
  作者：Kai Du、Shao‐Chien Wang、R. Sidick Basha、Chin‐Fa Lee

  DOI：10.1002/adsc.201800999

  日期：2019.4

  A first visible‐light photoredox‐catalyzed thioacetalization of aldehydes under metal‐free and solvent‐free conditions is described. Under blue LED irradiation, a reactive thiyl radical was initially generated through single‐electron oxidation of thiol, which subsequently reacted with aldehydes to afford dithioacetals following a radical mechanism. The reaction proceeded under ambient conditions, and

  描述了在无金属和无溶剂条件下醛的第一个可见光光氧化还原催化的硫代缩醛反应。在蓝光LED照射下，硫醇的单电子氧化首先产生了反应性的噻吩基，其随后通过自由基机理与醛反应生成二硫缩醛。反应在环境条件下进行，并且以良好至优异的产率提供了多种无环和环状二硫缩醛衍生物。
• Repairing the Thiol-Ene Coupling Reaction
  作者：Guillaume Povie、Anh-Tuan Tran、David Bonnaffé、Jacqueline Habegger、Zhaoyu Hu、Christine Le Narvor、Philippe Renaud

  DOI：10.1002/anie.201309984

  日期：2014.4.7

  AbstractThiol‐ene coupling (TEC) reactions emerged as one of the most useful processes for coupling different molecular units under reaction mild conditions. However, TEC reactions involving weak CH bonds (allylic and benzylic fragments) are difficult to run and often low yielding. Mechanistic studies demonstrate that hydrogen‐atom transfer processes at allylic and benzylic positions are responsible for the lack of efficiency of the radical‐chain process. These competing reactions cannot be prevented, but reported herein is a method to repair the chain process by running the reaction in the presence of triethylborane and catechol. Under these reaction conditions, a unique repair mechanism leads to an efficient chain reaction, which is demonstrated with a broad range of anomeric O‐allyl sugar derivatives including mono‐, di‐, and tetrasaccharides bearing various functionalities and protecting groups.
• US4013618A
  申请人：——

  公开号：US4013618A

  公开（公告）日：1977-03-22