1,1-dimethoxy-3-(4-tolylsulfonyl)propane | 104755-40-0

• 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: 1,1-dimethoxy-3-(4-tolylsulfonyl)propane
• 英文别名: 1-(3,3-dimethoxypropylsulfonyl)-4-methylbenzene
• CAS: 104755-40-0
• 化学式: C₁₂H₁₈O₄S
• 分子量: 258.339
• InChiKey: HZKRPHMKQTXZJQ-UHFFFAOYSA-N

物化性质

• 沸点：
  400.6±45.0 °C(Predicted)
• 密度：
  1.139±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  61
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,1-dimethoxy-3-(4-tolylsulfonyl)propane 在 甲醇 、 disodium hydrogenphosphate 、 正丁基锂 、 sodium amalgam 作用下， 反应 1.0h， 生成 4-(2,2-dimethoxyethyl)cyclopentene
  参考文献：
  名称：

  Dilithiated 3-tosylpropanal dimethyl acetal as β,β-acylvinyl dianion or homoenolate dianion equivalent

  摘要：

  3,3-Dilithio-1,1-dimethoxy-3-tosylpropane (6) reacts with mono and dielectrophiles to give dialkylated products 7 and carbocyclic derivatives 8, respectively. Hydrolysis of the acetal function followed by DBU dehydrosulfinylation of these products affords beta,beta-disubstituted propenal derivatives 11 and 12. Reductive desulfonylation of compounds 8g-j provides beta,beta-disubstituted propanal acetals 14.

  DOI：

  10.1016/s0040-4020(96)00072-5
• 作为产物：
  描述：

  3-p-Tolylsulfanyl-propionaldehyde 在 过氧乙酸 、 K-10 clay 作用下， 以 四氯化碳 为溶剂， 反应 3.0h， 生成 1,1-dimethoxy-3-(4-tolylsulfonyl)propane
  参考文献：
  名称：

  合成中的 1,4-双（芳基磺酰基）-1,2,3,4-四氢吡啶。高度区域选择性和立体选择性 SN1' 和烷基化反应

  摘要：

  锂化 β-磺酰基缩醛与氨基酸衍生的 N-甲苯磺酰基氮丙啶反应，然后酸催化环化，以良好的产率得到对映异构纯的 2-烷基 1,4-双（芳基磺酰基）-1,2,3,4-四氢吡啶 3。这些杂环底物在路易斯酸性条件下与一系列碳亲核试剂有效且高度立体选择性地反应，得到 SN1' 反应的 1,2,5,6-四氢吡啶产物，并进行锂化，然后在 4-位完全立体选择性地反应与卤代烷。

  DOI：

  10.1055/s-1998-1566

文献信息

• Lithiated 3-tosylpropanal and 4-tosyl-2-butanone dimethyl acetals as β-acylvinyl anion equivalents for the synthesis of unsaturated 1,4-dicarbonyl compounds and α,β-butenolides
  作者：Pedro Bonete、Carmen Nájera

  DOI：10.1016/0040-4020(95)00026-5

  日期：1995.2

  chlorides affords, after p-toluenesulfinic acid elimination, ene-1,4-dicarbonyl compounds in a stereoselective manner. In the case of compound 7a, derived from acrolein, sequential monolithiation and reaction with carbonyl compounds give cyclic acetals, which after oxidation and elimination of p-toluenesulfinic acid are transformed into α,β-butenolides.

  在对甲苯亚磺酸消除后，将1,1-二甲氧基-3-甲苯基丙烷（7a）和2,2-二甲氧基-4-甲苯基丁烷（7b）锂化，然后与酰氯反应，得到烯-1,4-二羰基立体选择性的化合物。在衍生自丙烯醛的化合物7a的情况下，顺序进行整体反应并与羰基化合物反应，得到环状缩醛，该缩醛在氧化和消除对甲苯磺酸后转化为α，β-丁烯内酯。
• Highly regioselective ring-opening of trisubstituted aziridines by sulfur-stabilised carbanions
  作者：Santiago Carballares、Donald Craig、Christopher J. T. Hyland、Pengfei Lu、Tanya Mathie、Andrew J. P. White

  DOI：10.1039/b815971h

  日期：——

  The highly regioselective, stereospecific ring-opening of trisubstituted N-tosylaziridines possessing vinyl and hydroxymethyl groups by sulfone- and sulfide-stablised carbanions is reported.

  报道了具有乙烯基和羟甲基的三取代N-对甲苯磺酰氮杂环丙烷在砜和硫化物稳定碳负离子的作用下，高度区域选择性和立体特异性的环开反应。
• MONOTHIOACETALIZATION OF ACETALS USING DIETHYLALUMINIUM THIOPHENOXIDE
  作者：Yukio Masaki、Yuzuru Serizawa、Kenji Kaji

  DOI：10.1246/cl.1985.1933

  日期：1985.12.5

  Reactions of diethylaluminium thiophenoxide (Et2AlSPh) with acetals of several types, in which acyclic, cyclic, and bicyclic ones are involved, were examined in comparison with the known reaction using thiophenol in the presence of Lewis acid and found to provide a new and efficient method for preparation of monothioacetals.

  与已知的在路易斯酸存在下使用苯硫酚的反应相比，检查了二乙基铝噻吩氧化物（Et2AlSPh）与几种类型的缩醛（其中涉及无环、环状和双环缩醛）的反应，并发现提供了一种新的有效方法用于制备单硫缩醛。
• Amide analogs of antifungal dioxane–triazole derivatives: Synthesis and in vitro activities
  作者：Takuya Uchida、Yoshiko Kagoshima、Toshiyuki Konosu

  DOI：10.1016/j.bmcl.2009.02.036

  日期：2009.4

  A new series of triazole compounds possessing an amide-part were efficiently synthesized and their in vitro antifungal activities were investigated. The amide analogs showed excellent in vitro activity against Candida, Cryptococcus and Aspergillus species. The MICs of compound 23d against C. albicans ATCC24433, C. neoformans TIMM1855 and A. fumigatus ATCC26430 were <= 0.008, 0.031 and 0.031 mu g/mL, respectively, (MICs of fluconazole: 0.5, >4 and >4 mu g/mL; MICs of itraconazole: 0.125, 0.25, 0.25 mu g/mL). Furthermore, compound 23d was stable under acidic conditions. (C) 2009 Elsevier Ltd. All rights reserved.
• 1,4-Bis(arylsulfonyl)dihydropyridines in synthesis. Enantioselective synthesis of 2,3,6-trisubstituted piperidines
  作者：Santiago Carballares、Donald Craig

  DOI：10.1016/s0022-328x(00)00918-9

  日期：2001.4

  A 2-substituted 1,4-bis (4-tolylsulfonyl)-1,2-dihydropyridine is readily accessed from an alpha -aminoester and 1,1-dimethoxy-3-(4-tolylsulfonyl)propane. This cyclic diene enters into highly selective addition reactions with carbon nucleophiles, and the product of one of these transformations is converted into a 2,3,6-trisubstituted piperidine via an S(N)1 ' reaction. (C) 2001 Elsevier Science B.V. All rights reserved.