tert-butyl 5-(bromomethyl)-2-methylbenzoate | 478977-50-3

• 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: tert-butyl 5-(bromomethyl)-2-methylbenzoate
• 英文别名: 1,1-dimethylethyl 5-(bromomethyl)-2-methylbenzoate
• CAS: 478977-50-3
• 化学式: C₁₃H₁₇BrO₂
• 分子量: 285.181
• InChiKey: MRUFGLTUIRXFJP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  tert-butyl 5-(bromomethyl)-2-methylbenzoate 在 4-二甲氨基吡啶 、 N-碘代丁二酰亚胺 、 三氟甲磺酸 、 sodium methylate 、 乙酸肼 、 四丁基碘化铵 、 二正丁基氧化锡 、 N,N'-二环己基碳二亚胺 、 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 63.17h， 生成 methyl O-(2-O-benzyl-4,6-O-benzylidene-β-D-glucopyranosyl)-(1 - 4)-2,3-di-O-benzyl-6-O-(3-methoxycarbonyl-4-methylbenzyl)-α-D-glucopyranoside
  参考文献：
  名称：

  Reiterative Intramolecular Glycosylation Supported by a Rigid Spacer

  摘要：

  This paper describes a synthesis of trisaccharide 1 by reiterative intramolecular glycosidation with 5-(bromomethyl)-2-methylbenzoic acid (5a) as starting material for the generation of a rigid spacer. Intramolecular glycosidation of donor-acceptor-tethered compound 24 yielded disaccharide 25. Transesterification of 25 afforded 26, which generated a new linking centre for the next spacer. Repetition of the previous cycle on 26 yielded trisaccharide 1, which again presents an extension point for the synthesis of higher saccharides. ((C) Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2003).

  DOI：

  10.1002/1099-0690(200301)2003:1<128::aid-ejoc128>3.0.co;2-s
• 作为产物：
  描述：

  对甲苯甲酸 在 磷酸 、 三氟化硼乙醚 、 氢溴酸 作用下， 以 二氯甲烷 、 环己烷 、 溶剂黄146 为溶剂， 反应 4.0h， 生成 tert-butyl 5-(bromomethyl)-2-methylbenzoate
  参考文献：
  名称：

  Reiterative Intramolecular Glycosylation Supported by a Rigid Spacer

  摘要：

  This paper describes a synthesis of trisaccharide 1 by reiterative intramolecular glycosidation with 5-(bromomethyl)-2-methylbenzoic acid (5a) as starting material for the generation of a rigid spacer. Intramolecular glycosidation of donor-acceptor-tethered compound 24 yielded disaccharide 25. Transesterification of 25 afforded 26, which generated a new linking centre for the next spacer. Repetition of the previous cycle on 26 yielded trisaccharide 1, which again presents an extension point for the synthesis of higher saccharides. ((C) Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2003).

  DOI：

  10.1002/1099-0690(200301)2003:1<128::aid-ejoc128>3.0.co;2-s

文献信息

• A New Base Mediated Method for the Cleavage of tert-Butyl Esters
  作者：Soumendu Paul、Richard R. Schmidt

  DOI：10.1055/s-2002-32583

  日期：——

  A new method for the cleavage of tert-butyl esters with NaH in DMF is described.

  一种在DMF中用NaH裂解叔丁酯的新方法被描述。
• [EN] FARNESOID X RECEPTOR AGONISTS<br/>[FR] AGONISTES DU RÉCEPTEUR DE FARNÉSOÏDE X
  申请人：SMITHKLINE BEECHAM CORP

  公开号：WO2009005998A1

  公开（公告）日：2009-01-08

  The present invention relates to famesoid X receptors (FXR, NR1H4) FXR is a member of the nuclear receptor class of ligand-activate transcription factors More particularly, the present invention relates to compounds useful as agonists for FXR, pharmaceutical formulations comprising such compounds, and therapeutic use of the same Novel isoxazole compounds are disclosed as part of pharmaceutical compositions for the treatment of a condition mediated by decreased FXR activity, such as obesity, diabetes, cholestatic liver disease, liver fibrosis, and metabolic syndrome

  本发明涉及法内索德X受体（FXR，NR1H4）。FXR是配体激活的转录因子核受体类的一个成员。更具体地说，本发明涉及作为FXR激动剂的化合物，包含该化合物的药物制剂，以及同一治疗用途。新颖的异恶唑化合物被披露作为药物组合物的一部分，用于治疗由FXR活性降低介导的状况，如肥胖、糖尿病、胆汁淤积性肝病、肝纤维化和代谢综合征。
• FARNESOID X RECEPTOR AGONISTS
  申请人：Akwabi-Ameyaw Adwoa

  公开号：US20110034507A1

  公开（公告）日：2011-02-10

  The present invention relates to farnesoid X receptors (FXR, NR1H4). FXR is a member of the nuclear receptor class of ligand-activate transcription factors. More particularly, the present invention relates to compounds useful as agonists for FXR, pharmaceutical formulations comprising such compounds, and therapeutic use of the same. Novel isoxazole compounds are disclosed as part of pharmaceutical compositions for the treatment of a condition mediated by decreased FXR activity, such as obesity, diabetes, cholestatic liver disease, liver fibrosis, and metabolic syndrome.

  本发明涉及法尼索德X受体（FXR，NR1H4）。FXR是配体激活转录因子的核受体类成员。更具体地，本发明涉及作为FXR激动剂有用的化合物，包含这些化合物的制药组合物以及其治疗用途。新型异唑咪唑化合物被揭示为用于治疗由FXR活性降低介导的疾病状态的制药组合物，例如肥胖症、糖尿病、胆汁淤积性肝病、肝纤维化和代谢综合征。
• Reiterative Intramolecular Glycosylation Supported by a Rigid Spacer
  作者：Soumendu Paul、Matthias Müller、Richard R. Schmidt

  DOI：10.1002/1099-0690(200301)2003:1<128::aid-ejoc128>3.0.co;2-s

  日期：2003.1

  This paper describes a synthesis of trisaccharide 1 by reiterative intramolecular glycosidation with 5-(bromomethyl)-2-methylbenzoic acid (5a) as starting material for the generation of a rigid spacer. Intramolecular glycosidation of donor-acceptor-tethered compound 24 yielded disaccharide 25. Transesterification of 25 afforded 26, which generated a new linking centre for the next spacer. Repetition of the previous cycle on 26 yielded trisaccharide 1, which again presents an extension point for the synthesis of higher saccharides. ((C) Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2003).