4-甲氧基苯基-1,3-二噻戊环 | 6712-20-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 4-甲氧基苯基-1,3-二噻戊环
• 英文名称: 2-(4-methoxyphenyl)-[1,3]dithiolane
• 英文别名: 4-methoxyphenyl-1,3-dithiolane；2-(p-methoxyphenyl)-1,3-dithiolane；2-(4-methoxyphenyl)-1,3-dithiolane
• CAS: 6712-20-5
• 化学式: C₁₀H₁₂OS₂
• 分子量: 212.337
• InChiKey: JYWZOJISGOBZDP-UHFFFAOYSA-N

物化性质

• 熔点：
  65 °C
• 沸点：
  140 °C(Press: 2 Torr)
• 密度：
  1?+-.0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  59.8
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2934999090

反应信息

• 作为反应物：
  描述：

  4-甲氧基苯基-1,3-二噻戊环 在 sodium tetrahydroborate 、 nickel(II) chloride hexahydrate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 0.58h， 以78%的产率得到对甲苯甲醚
  参考文献：
  名称：

  Nickel Boride–Mediated Cleavage of 1,3-Dithiolanes: A Convenient Approach to Reductive Desulfurization

  摘要：

  1,3-Dithiolanes are rapidly cleaved by nickel boride, generating corresponding hydrocarbons in excellent yields. The hydrogenolysis is rapid at room temperature and does not require protection from the atmosphere. Mild reaction conditions, simple workup, and good yields of pure products are some of the major advantages of the procedure.

  DOI：

  10.1080/00397910903340652
• 作为产物：
  描述：

  2-(4-甲氧基苯基)-1,3-二氧戊环 在 Kaolinitic clay 作用下， 生成 4-甲氧基苯基-1,3-二噻戊环
  参考文献：
  名称：

  Transdithioacetalization of acetals, ketals, oximes, enamines and tosylhydrazones catalysed by natural kaolinitic clay

  摘要：

  天然高岭土能高效催化缩醛、缩酮、肟、烯胺和甲苯磺酰腙与乙二硫醇和丙三硫醇的反式双硫缩醛化反应，以高产率生成相应的二硫杂环戊烷。

  DOI：

  10.1039/a706475f

文献信息

• 2,4,4,6-Tetrabromo-2,5-cyclohexadienone (TABCO), N-Bromosuccinimide (NBS) and Bromine as Efficient Catalysts for Dithioacetalization and Oxathioacetalization of Carbonyl Compounds and Transdithioacetalization Reactions
  作者：Nasser Iranpoor、Habib Firouzabadi、Hamid Reza Shaterian、M. A. Zolfigol

  DOI：10.1080/10426500211712

  日期：2002.5.1

  6-tetrabromo-2,5-cyclohexadienone (TABCO), N-bromosuccinimide (NBS), and bromine as efficient catalysts for conversion of carbonyl compounds to their cyclic and acyclic dithioacetals and 1,3-oxathiolanes under mild reaction conditions are described. These catalysts are also used for efficient transdithioacetalization of acetals, diacetals, ketals, acylals, enamines, hydrazones, and oximes with high

  使用 2,4,4,6-四溴-2,5-环己二烯酮 (TABCO)、N-溴代琥珀酰亚胺 (NBS) 和溴作为有效催化剂将羰基化合物转化为环状和无环二硫缩醛和 1,3-描述了在温和反应条件下的硫杂环戊烷。这些催化剂还用于在硫醇存在下以高产率有效地将缩醛、二缩醛、缩酮、酰基、烯胺、腙和肟转二硫缩醛。
• 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。
• A Facile Deprotection of Dithioacetals by FeCl₃/KI
  作者：Subhash P. Chavan、Priti B. Soni、Ramesh R. Kale、K. Pasupathy

  DOI：10.1081/scc-120016345

  日期：2003.1.4

  Abstract Carbonyl compounds were regenerated from corresponding dithioacetals via refluxing with FeCl3/KI and methanol as a solvent.

  摘要 羰基化合物由相应的二硫缩醛以FeCl3/KI和甲醇为溶剂回流再生。
• A Simple and Practical Synthetic Protocol for Acetalisation, Thioacetalisation and Transthioacetalisation of Carbonyl Compounds under Solvent-Free Conditions
  作者：Abu T. Khan、Ejabul Mondal、Subrata Ghosh、Samimul Islam

  DOI：10.1002/ejoc.200300685

  日期：2004.5

  corresponding dithioacetals under identical conditions. Some of the major advantages are mild reaction conditions, a high degree of efficiency, compatibilty with other protecting groups and the lack of solvents, particularly for thioacetalisation. In addition, no brominations occur at the double bond or α to the keto position or even in the aromatic ring under these experimental conditions. (© Wiley-VCH Verlag

  在室温下，在催化量的（溴二甲基）溴化锍存在下，用醇或二醇和原甲酸三乙酯处理后，多种羰基化合物可以顺利转化为相应的缩醛。类似地，在室温下使用相同的催化剂而无需任何溶剂，各种羰基化合物可以在与硫醇或二硫醇反应时转化为相应的二硫缩醛。此外，O,O-缩醛也可以在相同条件下转化为相应的二硫缩醛。一些主要优点是温和的反应条件、高效率、与其他保护基团的相容性以及缺乏溶剂，特别是对于硫代缩醛化。此外，在这些实验条件下，在双键或酮位的 α 处甚至芳环中都不会发生溴化。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)
• α,α-Diacetyl Cyclic Ketene Dithioacetals: Odorless and Efficient Dithiol Equivalents in Thioacetalization Reactions
  作者：Qun Liu、Dewen Dong、Haifeng Yu、Yanbing Yin、Qunxin Fang、Jingping Zhang

  DOI：10.1055/s-2004-822892

  日期：——

  Two novel, non-thiolic, odorless dithiol equivalents, α,α-diacetyl cyclic ketene dithioacetals 2a and 2b, had been developed. A range of carbonyl compounds 3 were converted into corresponding dithioacetals, dithianes 4 and dithiolanes 5, in high yields (up to 99%) in the presence of 2a or 2b. Moreover, 2a and 2b show high chemoselectivity between aldehyde and ketone in thioacetalization.

  开发了两种新型非硫醇类、无臭的二硫醇等效物，即α,α-二乙酰环状酮烯二硫缩酮2a和2b。一系列羰基化合物3在与2a或2b的存在下，高产率（高达99%）地转化为相应的二硫缩酮4和二硫醇环5。此外，2a和2b在硫缩酮化过程中对醛和酮显示出高度的化学选择性。