4-甲氧基苯甲醛三亚甲基二硫代缩醛 | 24588-72-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 4-甲氧基苯甲醛三亚甲基二硫代缩醛
• 中文别名: 2-(4'-甲氧基苯基)-1,3-二硫杂环己烷；2-(4-甲氧基苯基)-1,3-二硫代环己烷
• 英文名称: 2-(4-methoxyphenyl)-1,3-dithiane
• 英文别名: 4-methoxyphenyl-1,3-dithiane
• CAS: 24588-72-5
• 化学式: C₁₁H₁₄OS₂
• 分子量: 226.364
• InChiKey: INEZXIFHJBJBRB-UHFFFAOYSA-N

物化性质

• 熔点：
  121 °C
• 沸点：
  366.6±42.0 °C(Predicted)
• 密度：
  1.169±0.06 g/cm3(Predicted)
• 溶解度：
  溶于丙酮

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 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
• 储存条件：
  存放于惰性气体中，避免与空气接触。

反应信息

• 作为反应物：
  描述：

  4-甲氧基苯甲醛三亚甲基二硫代缩醛 在 bismuth(III) nitrate 作用下， 以 苯 为溶剂， 反应 4.5h， 以91%的产率得到4-甲氧基苯甲醛
  参考文献：
  名称：

  A novel method for the deprotection of S,S-acetals using air and a catalytic amount of bismuth (III) nitrate

  摘要：

  S,S-缩醛在环境条件下，以微量的五水合硝酸铋(III)为催化剂，可通过空气顺利去保护，生成高至极佳产率的原始羰基化合物。

  DOI：

  10.1039/cc9960001847
• 作为产物：
  描述：

  4-甲氧基苯基-1,3-二噻戊环 在 copper(II) sulfate 、 对苯醌 、 sodium iodide 作用下， 以 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 24.0h， 生成 4-甲氧基苯甲醛三亚甲基二硫代缩醛
  参考文献：
  名称：

  Facile deprotection of dithioacetals by using a novel 1,4-benzoquinone/cat. NaI system

  摘要：

  The combination of 1,4-benzoquinone and a catalytic amount of NaI was found to be effective for the deprotection of dithioacetals. The reactions proceeded efficiently under mild, near-neutral reaction conditions, producing a wide range of aryl and alkyl aldehydes and ketones generally in high yields with good functional group compatibility. The method developed therefore represents a general, facile, and highly applicable approach for deprotecting dithioacetals. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.08.061
• 作为试剂：
  描述：

  (Z)-2-iodo-1-(4-methoxyphenyl)ethanone O-methyloxime 在 正丁基锂 、 4-甲氧基苯甲醛三亚甲基二硫代缩醛 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 1.0h， 以0.43 g的产率得到2,2'-Bis-(4-methoxy-phenyl)-[2,2']bi[[1,3]dithianyl]
  参考文献：
  名称：

  1,3-Diphenylpropane-1,3-diamines XII [1]. A Novel Approach to Stereodefined Oximes and Oxime Ethers of Monothioketalized 1,3-Diketones and their Conversion to 3-Aminooximes

  摘要：

  Mono-O,O- and mono-S,S-ketals of 1,3-diphenylpropane-1,3-diones react with hydroxylamine hydrochloride and O-methylhydroxylamine hydrochloride affording mixtures of (E/Z) isomers which are hard to separate or an even unseparable. Isomerically pure oximes and O-methyloximes, however, are obtained either from 2-lithiated 1,3-dithianes and alpha-halogeno-oximes and alpha-halogeno-oxime ethers, resp., or from lithiated oxime ethers and dithienium salts. Reduction, acetylation, hydrolysis of the ketal increment, and oximation afford 3-amino-oximes which are precursors of 1,3-diphenylpropane-1,3-diamines.

  DOI：

  10.1007/pl00013502

文献信息

• Trichloroisocyanuric Acid, as an Industrial Chemical, Promotes Transthioacetalization of Diacetals of 2,2-Bis (Hydroxymethyl)-1,3-propanediol and Cleavage of Thioacetals
  作者：Habib Firouzabadi、Nasser Iranpoor、Hassan Hazarkhani

  DOI：10.1080/10426500214566

  日期：2002.11.1

  Trichloroisocyanuric acid has been used as a mild, efficient, and new catalyst for transthioacetalization of diacetals of 2,2-bis (hydroxymethyl)-1,3-propanediol in CH 2 Cl 2 at room temperature. A clean, easy, and general method for efficient deprotection of thioacetals to their corresponding carbonyl compounds using trichloroisocyanuric acid/silica gel and water system also is described.

  三氯异氰尿酸已被用作一种温和、高效的新型催化剂，用于室温下 CH 2 Cl 2 中 2,2-双（羟甲基）-1,3-丙二醇二缩醛的转硫代缩醛化反应。还描述了一种使用三氯异氰尿酸/硅胶和水系统将硫代缩醛有效脱保护为其相应羰基化合物的清洁、简单和通用的方法。
• 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。
• A Convenient Deprotection of 1,3-Dithiane Derivatives with Ferric Nitrate Under Heterogeneous Conditions
  作者：Masao Hirano、Ken Ukawa、Shigetaka Yakabe、Takashi Morimoto

  DOI：10.1080/00397919708006089

  日期：1997.5

  Abstract 1,3-Dithianes derived from aromatic, aliphatic, and alicyclic ketones or aldehydes can be conveniently converted to the parent carbonyl compounds with a combination of ferric nitrate and silica gel in hexane in excellent to quantitative yields.

  摘要 源自芳香族、脂肪族和脂环族酮或醛的 1,3-二噻烷可以通过硝酸铁和硅胶在己烷中的组合以优异的定量收率方便地转化为母体羰基化合物。
• A Useful and Environmentally Benign Synthetic Protocol for Dethiolization by Employing Vanadium Pentoxide Catalyzed Oxidation of Ammonium Bromide by Hydrogen Peroxide
  作者：Ejabul Mondal、Gopal Bose、Priti Rani Sahu、Abu T. Khan

  DOI：10.1246/cl.2001.1158

  日期：2001.11

  presence of olefin and aromatic ring as well as other protecting groups to carbonyl compounds by employing V2O5 catalyzed oxidation of ammonium bromide by H2O2 in CH2Cl2–H2O solvent system; mild conditions, high selectivity, good yield, and no side products such as bromination or oxidation are some of the major advantages.

  在 CH2Cl2–H2O 溶剂体系中，V2O5 催化 2 氧化溴化铵，在烯烃和芳环以及其他保护基团的存在下，多种硫缩醛和硫缩酮可以化学选择性地裂解为羰基化合物；温和的条件、高选择性、良好的收率以及无溴化或氧化等副产物是一些主要优点。
• Molten Salt as a Green Reaction Medium: Efficient and Chemoselective Dithioacetalization and Oxathioacetalization of Aldehydes Mediated by Molten Tetrabutylammonium Bromide
  作者：Brindaban C. Ranu、Arijit Das

  DOI：10.1071/ch03318

  日期：——

  Tetrabutylammonium bromide in the molten state has been demonstrated to be a very efficient catalyst and reaction medium for the highly chemoselective dithioacetalization and oxathioacetalization of aldehydes. The tetrabutylammonium bromide is recycled for subsequent reactions.

  熔融状态的四丁基溴化铵已被证明是一种非常有效的催化剂和反应介质，可用于醛的高化学选择性二硫代缩醛化和氧硫代缩醛化。四丁基溴化铵被循环用于后续反应。

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