methyl 4-(benzyloxy)-2-bromo-5-methoxybenzoate | 139963-13-6

• 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: methyl 4-(benzyloxy)-2-bromo-5-methoxybenzoate
• 英文别名: Benzoic acid, 2-bromo-5-methoxy-4-(phenylmethoxy)-, methyl ester；methyl 2-bromo-5-methoxy-4-phenylmethoxybenzoate
• CAS: 139963-13-6
• 化学式: C₁₆H₁₅BrO₄
• 分子量: 351.197
• InChiKey: MFAJIFRJEGMYNB-UHFFFAOYSA-N

物化性质

• 沸点：
  434.5±40.0 °C(Predicted)
• 密度：
  1.392±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 4-(benzyloxy)-2-bromo-5-methoxybenzoate 在 palladium on activated charcoal 吡啶 、 lithium aluminium tetrahydride 、 四(三苯基膦)钯 、 氢气 、 sodium methylate 、 sodium 、 三溴化磷 、 碳酸氢钠 、 potassium carbonate 、 1,1,2,2-四苯乙烯 、 potassium iodide 作用下， 以 甲醇 、 乙醚 、 乙醇 、 乙酸乙酯 、 丙酮 、 苯 为溶剂， 反应 11.83h， 生成 Plagiochin C-triacetate
  参考文献：
  名称：

  Total synthesis of plagiochins C and D, macrocyclic bis(bibenzyl) constituents of plagiochila acantophylla

  摘要：

  Plagiochins C (3) and D (4) were synthesized by convergent schemes. Rings C and B were joined by Ullman ether synthesis, the aryl-aryl bond between rings A and D was formed by Pd(0)-catalysed coupling of an arylboronic acid (ring D) and a bromobenzoic ester (ring A). Ring C and D were linked by the Wittig reaction, while final ring closure was effected by tetraphenylethene assisted Wurtz reaction.

  DOI：

  10.1016/s0040-4020(01)88193-x
• 作为产物：
  描述：

  甲醇 、 Benzyl 4-benzyloxy-2-bromo-5-methoxybenzoate 在 盐酸 作用下， 反应 16.0h， 以90%的产率得到methyl 4-(benzyloxy)-2-bromo-5-methoxybenzoate
  参考文献：
  名称：

  Total synthesis of plagiochins C and D, macrocyclic bis(bibenzyl) constituents of plagiochila acantophylla

  摘要：

  Plagiochins C (3) and D (4) were synthesized by convergent schemes. Rings C and B were joined by Ullman ether synthesis, the aryl-aryl bond between rings A and D was formed by Pd(0)-catalysed coupling of an arylboronic acid (ring D) and a bromobenzoic ester (ring A). Ring C and D were linked by the Wittig reaction, while final ring closure was effected by tetraphenylethene assisted Wurtz reaction.

  DOI：

  10.1016/s0040-4020(01)88193-x

文献信息

• Allylic Arylation of 1,3-Dienes via Hydroboration/Migrative Suzuki–Miyaura Cross-Coupling Reactions
  作者：Xiao-Ming Zhang、Jie Yang、Qing-Bo Zhuang、Yong-Qiang Tu、Zongyuan Chen、Hui Shao、Shao-Hua Wang、Fu-Min Zhang

  DOI：10.1021/acscatal.8b01823

  日期：2018.7.6

  The hydroboration/Pd-catalyzed migrative Suzuki–Miyaura cross-coupling of 1,3-dienes with electron-deficient aryl halides has been developed, which enables the synthesis of branched allylarenes directly from primary homoallylic alkyl boranes. A ligand-tuned linear- or branch-selective coupling for these aryl halides has also been achieved.

  1,3-二烯与缺电子的芳基卤化物的加氢硼化/ Pd催化迁移性Suzuki-Miyaura交叉偶联已经发展，这使得直接从伯均烯丙基烷基硼烷直接合成支链烯丙基芳烃成为可能。对于这些芳基卤化物，也已经实现了配体调谐的线性或分支选择性偶联。
• PYRROLOBENZODIAZEPINE ANTIBODY DRUG CONJUGATES AND METHODS OF USE
  申请人：Genentech, Inc.

  公开号：US20170095570A1

  公开（公告）日：2017-04-06

  The invention provides antibody-drug conjugates comprising an antibody conjugated to a pyrrolobenzodiazepine drug moiety via a disulfide linker, pyrrolobenzodiazepine linker-drug intermediates, and methods of using the antibody-drug conjugates.

  本发明提供了包含通过二硫键连接器将抗体与吡咯并苯二氮卓药物部分连接的抗体药物偶联物、吡咯并苯二氮卓连接器-药物中间体，以及使用抗体药物偶联物的方法。
• Pyrrolobenzodiazepine antibody drug conjugates and methods of use
  申请人：Genentech, Inc.

  公开号：US10058613B2

  公开（公告）日：2018-08-28

  The invention provides antibody-drug conjugates comprising an antibody conjugated to a pyrrolobenzodiazepine drug moiety via a disulfide linker, pyrrolobenzodiazepine linker-drug intermediates, and methods of using the antibody-drug conjugates.

  本发明提供了抗体-药物共轭物，包括通过二硫连接体与吡咯并二氮杂卓药物分子共轭的抗体、吡咯并二氮杂卓连接体-药物中间体，以及使用抗体-药物共轭物的方法。
• Total synthesis of plagiochins C and D, macrocyclic bis(bibenzyl) constituents of plagiochila acantophylla
  作者：György M. Keserü、Gabriella Mezey-Vándor、Mihály Nógrádi、Borbála Vermes、Mária Kajtár-Peredy

  DOI：10.1016/s0040-4020(01)88193-x

  日期：——

  Plagiochins C (3) and D (4) were synthesized by convergent schemes. Rings C and B were joined by Ullman ether synthesis, the aryl-aryl bond between rings A and D was formed by Pd(0)-catalysed coupling of an arylboronic acid (ring D) and a bromobenzoic ester (ring A). Ring C and D were linked by the Wittig reaction, while final ring closure was effected by tetraphenylethene assisted Wurtz reaction.