3-甲氧基-5-(甲氧基羰基)苯硼酸频那醇酯 | 889654-06-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 3-甲氧基-5-(甲氧基羰基)苯硼酸频那醇酯
• 中文别名: 3-甲氧基-5-(甲氧羰基)苯基硼酸频哪醇酯；3-甲氧基-5-(4,4,5,5-四甲基-1,3,2-二氧杂环己硼烷-2-基)苯甲酸甲酯
• 英文名称: methyl 3-methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate
• CAS: 889654-06-2
• 化学式: C₁₅H₂₁BO₅
• 分子量: 292.14
• InChiKey: ZBLGLKWSVGSAQD-UHFFFAOYSA-N

物化性质

• 沸点：
  407.8±35.0 °C(Predicted)
• 密度：
  1.11±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.78
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

安全信息

• 海关编码：
  2934999090
• 危险性防范说明：
  P261,P264,P271,P280,P302+P352,P304+P340+P312,P305+P351+P338,P332+P313,P337+P313,P362,P403+P233,P405,P501
• 危险性描述：
  H315,H319,H335

反应信息

• 作为反应物：
  描述：

  3-甲氧基-5-(甲氧基羰基)苯硼酸频那醇酯 在 四(三苯基膦)钯 、 potassium carbonate 、 三苯基膦 、 potassium hydroxide 作用下， 以 乙醇 、 水 、 邻二氯苯 、 甲苯 为溶剂， 反应 29.0h， 生成 1-甲氧基咔唑-3-羧酸
  参考文献：
  名称：

  咔唑生物碱的全合成

  摘要：

  Suzuki-Miyaura交叉偶联，然后是三苯基膦介导的Cadogan还原环化序列，提供了对一系列咔唑生物碱的有效利用。 在目前的工作中，该方法已应用于总的合成，其中包括穆科宁，clauszoline K，koenoline，murrayanine，murrayafoline A，mukoeic acid，glycorborine，glycolzolicine，mukolidine，mukoline，glycozoline，3-甲氧基-9 H-咔唑-1-羧酸甲酯，（3-甲氧基-9 H-咔唑-1-基）-甲醇，3-甲氧基-9 H-咔唑-1-甲醛，3-甲氧基-9 H-咔唑-1-羧酸，2 -甲基-9 H-咔唑和非甾体抗炎药（NSAID）卡洛芬及其衍生物。

  DOI：

  10.1016/j.tet.2019.01.003
• 作为产物：
  描述：

  3-羟基-5-甲氧基苯甲酸甲酯 在 2,6-二甲基吡啶 、 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 potassium acetate 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 16.0h， 生成 3-甲氧基-5-(甲氧基羰基)苯硼酸频那醇酯
  参考文献：
  名称：

  Targeting the Heat Shock Protein 90 Dimer with Dimeric Inhibitors

  摘要：

  The design, synthesis, and biological evaluation of conformationally constrained coumermycin Al analogues are reported. Compounds were evaluated against both breast cancer (SKBr3 and MCF7) and prostate cancer (PC3 mm2, A549, and HT29) cell lines. Non-noviosylated coumermycin Al analogues that manifest potent antiproliferative activity resulting from Hsp90 inhibition are provided, wherein replacement of the stereochemically complex noviose sugar with readily available piperidine rings resulted in similar to 100 fold increase in antiproliferative activities as compared to coumermycin Al, producing small molecule Hsp90 inhibitors that exhibit nanomolar activities.

  DOI：

  10.1021/jm200553w

文献信息

• NOVEL TRICYCLIC COMPOUNDS AS ANTICANCER AGENTS
  申请人：BRISTOL-MYERS SQUIBB COMPANY

  公开号：US20160176864A1

  公开（公告）日：2016-06-23

  The present invention is directed to tricyclic compounds, pharmaceutically acceptable compositions comprising compounds of the invention and methods of using said compositions in the treatment of various disorders.

  本发明涉及三环化合物，其中包括本发明化合物的药学可接受组合物以及使用该组合物治疗各种疾病的方法。
• Synthesis of Diverse 3-Azido-5-(azidomethyl)benzene Derivatives via Formal C–H Azidation and Functional Group-Selective Transformations
  作者：Takamitsu Hosoya、Suguru Yoshida、Yoshitake Nishiyama、Yoshihiro Misawa、Yuki Hazama、Kazuhiro Oya

  DOI：10.3987/com-18-s(f)72

  日期：——
• Discovery of a Novel Series of Benzoic Acid Derivatives as Potent and Selective Human β₃ Adrenergic Receptor Agonists with Good Oral Bioavailability. 3. Phenylethanolaminotetraline (PEAT) Skeleton Containing Biphenyl or Biphenyl Ether Moiety
  作者：Masashi Imanishi、Yutaka Nakajima、Yasuyo Tomishima、Hitoshi Hamashima、Kenichi Washizuka、Minoru Sakurai、Shigeo Matsui、Emiko Imamura、Koji Ueshima、Takao Yamamoto、Nobuhiro Yamamoto、Hirofumi Ishikawa、Keiko Nakano、Naoko Unami、Kaori Hamada、Yasuhiro Matsumura、Fujiko Takamura、Kouji Hattori

  DOI：10.1021/jm800222k

  日期：2008.8.1

  We designed a series of benzoic acid derivatives containing the biphenyl ether or biphenyl template on the RHS and a phenylethanolaminotetraline (PEAT) skeleton, which was prepared by highly stereoselective synthesis, to generate two structurally different lead compounds (10c, 10m) with a good balance of potency, selectivity, and pharmacokinetic profile. Further optimization of the two lead compounds to improve potency led to several potential candidates (i.e., 11f, 11l, 11o, 12b). In particular, biphenyl analogue 12b exhibited an excellent balance of high potency (EC(50) = 0.38 nM) for beta(3), high selectivity over beta(1) and beta(2), and good pharmacokinetic properties in rats, dogs, and monkeys.