1-nitro-4-triphenylmethyloxymethylbenzene | 39834-49-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: 1-nitro-4-triphenylmethyloxymethylbenzene
• 英文别名: 4-nitrobenzyl trityl ether；(((4-nitrobenzyl)oxy)methanetriyl)tribenzene；Trityl-p-nitrobenzylaether；(4-Nitro-benzyl)-trityl-aether；1,1',1''-{[(4-Nitrophenyl)methoxy]methanetriyl}tribenzene；1-nitro-4-(trityloxymethyl)benzene
• CAS: 39834-49-6
• 化学式: C₂₆H₂₁NO₃
• 分子量: 395.458
• InChiKey: VBYWHMLEGJZXAD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  30
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  55
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-nitro-4-triphenylmethyloxymethylbenzene 在 nanoporous MCM-41-SO₃H 作用下， 以 乙腈 为溶剂， 反应 0.67h， 以100%的产率得到对硝基苯甲醇
  参考文献：
  名称：

  Highly efficient protection of alcohols as trityl ethers under solvent-free conditions, and recovery catalyzed by reusable nanoporous MCM-41-SO3H

  摘要：

  简历摘要 一种高效的方法被开发出来，用于在室温下使用无溶剂球磨法，通过纳米孔道MCM-41-SO3H作为非均相催化剂，在三苯甲醇存在下保护醇为三苯甲醚。这种新的无溶剂和环保方法的优点包括低催化剂负载量、高效率和可重复使用性。所生成的三苯甲醚的去保护过程同样在该催化剂作用下于湿乙腈中高效完成。

  DOI：

  10.1016/j.crci.2014.01.003
• 作为产物：
  描述：

  (三苯甲氧基甲基)苯 在 nanoporous MCM-41-SO₃H 作用下， 以 乙腈 为溶剂， 反应 2.5h， 生成 1-nitro-4-triphenylmethyloxymethylbenzene
  参考文献：
  名称：

  Highly efficient protection of alcohols as trityl ethers under solvent-free conditions, and recovery catalyzed by reusable nanoporous MCM-41-SO3H

  摘要：

  简历摘要 一种高效的方法被开发出来，用于在室温下使用无溶剂球磨法，通过纳米孔道MCM-41-SO3H作为非均相催化剂，在三苯甲醇存在下保护醇为三苯甲醚。这种新的无溶剂和环保方法的优点包括低催化剂负载量、高效率和可重复使用性。所生成的三苯甲醚的去保护过程同样在该催化剂作用下于湿乙腈中高效完成。

  DOI：

  10.1016/j.crci.2014.01.003

文献信息

• Design and synthesis of inositolphosphoglycan putative insulin mediators
  作者：Javier López-Prados、Félix Cuevas、Niels-Christian Reichardt、José-Luis de Paz、Ezequiel Q. Morales、Manuel Martín-Lomas

  DOI：10.1039/b418041k

  日期：——

  results from the biological evaluation of these molecules provide additional support to an insulin-mediated signalling system which involves the intermediacy of inositolphosphoglycans as putative insulin mediators.

  使用分子对接分析了一系列包含葡糖胺（1→6）肌醇结构基序的分子与cAMP依赖性蛋白激酶（PKA）催化亚基的ATP结合位点的结合模式。这些计算预测假二糖和假三糖结构中非还原端的磷酸基团的存在将分子正确地定向到结合位点，并且假三糖结构呈现出最佳的形状互补性。因此，已经使用有效的合成策略从常见的中间体合成了伪二糖和伪三糖。基于这种合成化学，已经探索了使用相同的中间体在固相上构建小的假三糖文库的可行性。
• KMnO₄-catalyzed chemoselective deprotection of acetate and controllable deacetylation–oxidation in one pot
  作者：Aakanksha Gurawa、Manoj Kumar、Dodla S. Rao、Sudhir Kashyap

  DOI：10.1039/d0nj04321d

  日期：——

  deacetylation under ambient conditions was developed using catalytic KMnO4. The stoichiometric use of KMnO4 highlighted the dual role of a heterogeneous oxidant enabling direct access to aromatic aldehydes in one-pot sequential deacetylation–oxidation. The reaction employed an alternative solvent system and allowed the clean transformation of benzyl acetate to sensitive aldehyde in a single step while

  利用催化的KMnO 4，开发了一种在环境条件下进行化学选择性脱乙酰反应的新型有效方案。KMnO 4的化学计量使用突显了一种异质氧化剂的双重作用，该异质氧化剂可在一锅顺序进行的脱乙酰基氧化反应中直接进入芳族醛。该反应采用另一种溶剂体系，并允许乙酸苄基酯在一个步骤中从干净转化为敏感的醛，同时防止过度氧化成酸。使用廉价且易于获得的KMnO 4作为环境友好的试剂以及反应操作的简便性特别吸引人，并且使得在先前步骤中乙酸盐的受控氧化和易裂解成为可能。
• Nickel-Catalyzed Reductive Benzylation of Aldehydes with Benzyl Halides and Pseudohalides
  作者：Farhad Panahi、Marzieh Bahmani、Nasser Iranpoor

  DOI：10.1002/adsc.201400970

  日期：2015.4.13

  benzylation of aromatic and aliphatic aldehydes with benzylic halides is reported using a nickel/zinc catalyst system. In addition to benzylic halides, the first report on the addition of benzylic triflates, acetates, tosylates and tritylates to aldehydes is also presented. By this new method a range of alcohols was synthesized efficiently from aldehydes and benzylic substrates at room temperature in moderate

  据报道，使用镍/锌催化剂体系可将芳族和脂族醛与苄基卤化物进行还原性苄基化反应。除苄基卤化物外，还首次报道了向醛中添加苄基三氟甲磺酸酯，乙酸酯，甲苯磺酸酯和三苯甲酸酯的方法。通过这种新方法，可以在室温下从醛和苄基底物中高效合成中度到高产率的多种醇。温和的反应条件和良好的官能团耐受性使这种镍催化的方法可用于合成各种苄醇。
• Zinc chloride homogeneous catalysis in the tritylation of hydroxyl- and amide-bearing molecules
  作者：Maurizio Maltese、Maria Cecilia Vergari、Maria Pia Donzello

  DOI：10.1016/j.tetlet.2010.11.095

  日期：2011.1

  A tritylation protocol based on the transfer of the triphenylmethylcarbenium ion from trityl acetate to substrates having hydroxyls, in the presence of catalytic amounts of ZnCl2, is described. The advantages of this method are broad scope, mild conditions, and easy handling. The comparison with the procedure based on the use of equimolar mixture of TrCl and ZnCl2 in the presence of TEA shows that

  描述了在催化量的ZnCl 2存在下基于三苯甲基碳鎓离子从乙酸三苯甲基酯转移至具有羟基的底物的三苯甲基化方案。该方法的优点是适用范围广，条件温和且易于操作。与基于在TEA存在下使用TrCl和ZnCl 2等摩尔混合物的方法的比较表明，获得了可比较的结果。但是，只有这种方法才能抑制仲醇或苄醇的反应，例如氧化或对称醚的形成。两种方法都成功地扩展到简单和取代的酰胺。不管其在乙腈中的溶解度如何，即使是天冬酰胺也可以直接在其酰胺基上三苯甲基化。
• (3R,5R)-7-(2-(4-플루오로페닐)-5-이소프로필-3-페닐-4-((4-히드록시메틸페닐아미노)카보닐)-피롤-1-일)-3,5-디히드록시 헵탄산 헤미칼슘염의 제조방법, 이에 사용되는 중간체, 및 중간체의 제조방법
  申请人：DAE WON PHARMACEUTICAL CO., LTD 대원제약주식회사(119980007184) Corp. No ▼ 110111-0103955BRN ▼207-81-36336

  公开号：KR102001835B1

  公开（公告）日：2019-07-19

  본 발명은 (3R,5R)-7-(2-(4-플루오로페닐)-5-이소프로필-3-페닐-4-((4-히드록시 메틸 페닐 아미노)카보닐)-피롤-1-일)-3,5-디히드록시 헵탄산 헤미칼슘염의 제조방법, 이에 사용되는 중간체 및 이의 제조방법을 제공한다. 본 발명의 제조방법은, (3R,5R)-7-(2-(4-플루오로페닐)-5-이소프로필-3-페닐-4-((4-히드록시메틸페닐아미노)카보닐)-피롤-1-일)-3,5-디히드록시 헵탄산 헤미칼슘염의 주요 구조부들 각각을 개별적으로 합성한 후 커플링 하는 수렴합성 방식으로 수행된다. 이에 따라, 유연물질을 용이하게 제어하고 제조시간을 단축시킬 수 있어 화합물의 생산성을 향상시킬 수 있고, 최종 화합물의 수율 또한 높일 수 있다.

  This invention provides a method for preparing (3R,5R)-7-(2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-((4-hydroxymethylphenylamino)carbonyl)-pyrrol-1-yl)-3,5-dihydroxy heptanoic acid hemicalcium salt, an intermediate used therein, and a method for preparing the same. The preparation method of the present invention is carried out by synthesizing each major structural moiety of (3R,5R)-7-(2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-((4-hydroxymethylphenylamino)carbonyl)-pyrrol-1-yl)-3,5-dihydroxy heptanoic acid hemicalcium salt separately and then coupling them in a convergent synthesis approach. Accordingly, the flexibility of the material can be easily controlled, the manufacturing time can be shortened, thus improving the productivity of the compound, and the yield of the final compound can also be increased.