5-溴-2-甲氧基甲苯磺酸苯酯 | 871571-19-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 5-溴-2-甲氧基甲苯磺酸苯酯
• 英文名称: 5-bromo-2-methoxyphenyl methanesulfonate
• 英文别名: (5-bromo-2-methoxyphenyl) methanesulfonate
• CAS: 871571-19-6
• 化学式: C₈H₉BrO₄S
• 分子量: 281.127
• InChiKey: GNSGHHSZKANUDW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  61
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 海关编码：
  2909499000

反应信息

• 作为反应物：
  描述：

  5-溴-2-甲氧基甲苯磺酸苯酯 在 sodium hydroxide 、 potassium carbonate 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 17.0h， 生成 2-(苄氧基)-4-溴苯甲醚
  参考文献：
  名称：

  利用电生成的高反应性锌方便地制备有机溴化锌及其在交叉偶联反应中的应用

  摘要：

  通过电解含有containing作为介体的DMF溶液以及铂阴极和锌阳极，可以轻松制备高反应性锌。发生refer的优先还原以生成相应的自由基阴离子，该自由基阴离子还原了由阳极溶解生成的锌离子，从而获得了具有高反应活性的零价锌。反应性锌已成功用于将溴代烷烃有效转化为相应的有机锌溴化物。所获得的有机锌溴化物进一步成功地用于Pd催化的与各种芳基碘化物和溴化物的交叉偶联反应中。

  DOI：

  10.1016/j.tet.2005.09.031
• 作为产物：
  描述：

  2-methoxyphenyl mesylate 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以96%的产率得到5-溴-2-甲氧基甲苯磺酸苯酯
  参考文献：
  名称：

  薄片蛋白D，L和N的全合成

  摘要：

  通过使用Hinsberg型吡咯合成法和钯催化的3,4-二羟基吡咯二酚6的Suzuki-Miyaura偶联，已经完成了细胞毒性海洋生物碱，薄片蛋白D，L和N的总合成。普通中间体6的层状蛋白D，L和N的总产率分别为54％，58％和50％。

  DOI：

  10.1016/j.tet.2005.10.014

文献信息

• Total synthesis of lamellarins D, L, and N
  作者：Naotaka Fujikawa、Takeshi Ohta、Tomohiro Yamaguchi、Tsutomu Fukuda、Fumito Ishibashi、Masatomo Iwao

  DOI：10.1016/j.tet.2005.10.014

  日期：2006.1

  Total synthesis of cytotoxic marine alkaloids, lamellarins D, L, and N, has been achieved by using Hinsberg-type pyrrole synthesis and palladium-catalyzed Suzuki–Miyaura coupling of the 3,4-dihydroxypyrrole bistriflate 6 as the key reactions. The total yields of lamellarins D, L, and N from the common intermediate 6 are 54, 58, and 50%, respectively.

  通过使用Hinsberg型吡咯合成法和钯催化的3,4-二羟基吡咯二酚6的Suzuki-Miyaura偶联，已经完成了细胞毒性海洋生物碱，薄片蛋白D，L和N的总合成。普通中间体6的层状蛋白D，L和N的总产率分别为54％，58％和50％。
• PROCESS FOR PREPARING AN ORTHO-SUBSTITUTED 5-HALOPHENOL AND A SYNTHESIS INTERMEDIATE THEREOF
  申请人：Mercier Claude

  公开号：US20130066097A1

  公开（公告）日：2013-03-14

  A process for preparing a 5-halophenol, ortho-substituted by an electron-donating group, is described. Also described, is a process for preparing a sulphonic ester of an ortho-substituted phenol, which is the synthesis intermediate for the ortho-substituted 5-halophenol. The process for preparing a phenol ortho-substituted by an electron-donating group and protected in the form of a sulphonic ester can include reacting a phenol ortho-substituted by an electron-donating group with a sulphonylating agent in the presence of a Lewis acid. The process for preparing a 5-halophenol ortho-substituted by an electron-donating group can include a first step of preparing a phenol ortho-substituted by an electron-donating group and protected in the form of a sulphonic ester, as described above; a second step of halogenating the protected phenol intermediate obtained in the preceding step, in the position para to the electron-donating group; and a third step of deprotecting the sulphonic ester function to hydroxyl.

  描述了一种制备5-卤酚的过程，其邻位取代为电子给予基团。还描述了一种制备邻位取代酚的磺酸酯的过程，该酚是邻位取代的5-卤酚的合成中间体。制备邻位取代酚的过程，该酚的邻位取代为电子给予基团，并以磺酸酯的形式保护，可以包括在Lewis酸的存在下，将邻位取代为电子给予基团的酚与磺化试剂反应。制备邻位取代为电子给予基团的5-卤酚的过程可以包括以下步骤：首先，制备如上所述的邻位取代为电子给予基团并以磺酸酯形式保护的酚；其次，在前述步骤中获得的保护酚中间体中，在电子给予基团对位进行卤代反应；最后，去除磺酸酯功能以得到羟基。
• [EN] PROCESS FOR PREPARING AN ORTHO-SUBSTITUTED 5-HALOPHENOL AND A SYNTHESIS INTERMEDIATE THEREOF<br/>[FR] PROCÉDÉ POUR LA PRÉPARATION D'UN 5-HALOGÉNOPHÉNOL ORTHO-SUBSTITUÉ ET SON INTERMÉDIAIRE DE SYNTHÈSE
  申请人：RHODIA CHINA CO LTD

  公开号：WO2011143819A1

  公开（公告）日：2011-11-24

  Disclosed a process for preparing a phenol ortho-substituted by an electron-donating group and protected in the form of a sulphonic ester which comprises reacting a phenol ortho- substituted by an electron-donating group with a sulphonylating agent in the presence of an effective amount of a Lewis acid and a process for preparing a 5-halophenol ortho- substituted which comprises a firste step of preparing a phenol ortho-substituted by an electron-donating group and protected in the form of a sulphonic ester, as described above, a second step of halogenating the protected phenol intermediate obtained in the preceding step, in the position para to the electron-donating group, and a third step of deprotecting the sulphonic ester function to hydroxyl

  揭示了一种制备含电子给体基团的酚邻位取代的过程，并以磺酸酯形式保护，包括在有效量的Lewis酸存在下，将含电子给体基团的酚邻位取代物与磺化试剂反应的过程，以及一种制备5-卤代酚邻位取代的过程，包括第一步制备如上所述的含电子给体基团的酚邻位取代物并以磺酸酯形式保护，第二步在前一步得到的受保护酚中间体上对位于电子给体基团的位置进行卤代反应，第三步去除磺酸酯功能以得到羟基。
• Facile preparation of organozinc bromides using electrogenerated highly reactive zinc and its use in cross-coupling reaction
  作者：Nobuhito Kurono、Tomio Inoue、Masao Tokuda

  DOI：10.1016/j.tet.2005.09.031

  日期：2005.11

  to give zero valent zinc with high reactivity. The reactive zinc was successfully used for an efficient transformation of bromoalkanes into the corresponding organozinc bromides. Organozinc bromides obtained were further used successfully in Pd-catalyzed cross-coupling reaction with various aryl iodides and bromides.

  通过电解含有containing作为介体的DMF溶液以及铂阴极和锌阳极，可以轻松制备高反应性锌。发生refer的优先还原以生成相应的自由基阴离子，该自由基阴离子还原了由阳极溶解生成的锌离子，从而获得了具有高反应活性的零价锌。反应性锌已成功用于将溴代烷烃有效转化为相应的有机锌溴化物。所获得的有机锌溴化物进一步成功地用于Pd催化的与各种芳基碘化物和溴化物的交叉偶联反应中。
• Synthesis and biological evaluation of a 2-aryl polyhydroxylated pyrrolidine alkaloid-based library
  作者：En-Lun Tsou、Sih-Yu Chen、Ming-Hsun Yang、Shih-Chi Wang、Ting-Ren Rachel Cheng、Wei-Chieh Cheng

  DOI：10.1016/j.bmc.2008.10.063

  日期：2008.12.15

  Inspired by polyhydroxylated pyrrolidine alkaloid natural products, a 18-membered library of 2-aryl polyhydroxylated pyrrolidines has been efficiently prepared in two or three synthetic steps from the known chiral cyclic nitrones with high yield and purity and excellent stereoselectivity. The inhibitory activity of all these compounds against various glycosidase enzymes was evaluated. Interestingly, 15 and 19 show better inhibitory activities than radicamine A ( 20) and B ( 18) against alpha-glucosidases. The IC50 values of 15 and 19 are 1.1 and 0.5 mu M, respectively. In this study, we also discovered the substituent(s) on the aryl ring could affect the inhibition potency and selectivity against glycosidases. (C) 2008 Elsevier Ltd. All rights reserved.