benzyl 3-hydroxy-4-methoxybenzoate

• 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: benzyl 3-hydroxy-4-methoxybenzoate
• 英文别名: benzyl isovanillate
• 化学式: C₁₅H₁₄O₄
• 分子量: 258.274
• InChiKey: JCDXRQAHAUKPMH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  benzyl 3-hydroxy-4-methoxybenzoate 在 4-二甲氨基吡啶 、 palladium 10% on activated carbon 、 甲酸铵 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 46.0h， 生成 4-methoxy-3-sulfooxybenzoic acid monoammonium salt
  参考文献：
  名称：

  Flavonoid metabolism: the synthesis of phenolic glucuronides and sulfates as candidate metabolites for bioactivity studies of dietary flavonoids

  摘要：

  Epidemiological studies indicate that flavonoid intake is inversely associated with the risk of coronary heart disease, yet the mechanisms responsible for their bioactivity are still a matter of debate. Based on the rapid and extensive metabolism of most flavonoids, their health effects most likely result from the biological activity of their metabolites. However, a lack of commercially available compounds/standards has prevented the study of metabolite bioactivity and resulted in a focus on non-physiologically relevant precursor/parent structures. This paper details the synthesis of a series of phenolic glucuronide 1a-e and sulfate 2a-e derivates as candidate metabolites for use as reference compounds in metabolic profiling studies and for the exploration of flavonoid bioactivity. (C) 2012 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2012.03.100
• 作为产物：
  描述：

  3-羟基-4-甲氧基苯甲酸 、 溴甲苯 在 potassium carbonate 作用下， 生成 benzyl 3-hydroxy-4-methoxybenzoate
  参考文献：
  名称：

  Novel and potent inhibitors of stearoyl-CoA desaturase-1. Part I: Discovery of 3-(2-hydroxyethoxy)-4-methoxy-N-[5-(3-trifluoromethylbenzyl)thiazol-2-yl]benzamide

  摘要：

  A series of structurally novel stearoyl-CoA desaturase-1 (SCD-1) inhibitors has been identified by optimizing a hit from our corporate library. Preliminary structure-activity relationship (SAR) studies led to the discovery of the highly potent and orally bioavailable thiazole-based SCD-1 inhibitor, 3-(2-hydroxyethoxy)-4-methoxy-N-[5-(3-trifluoromethylbenzyl)thiazol-2-yl]benzamide (23a). (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.05.119

文献信息

• Methods for forming combinatorial libraries combining amide bond formation with epoxide opening
  申请人：——

  公开号：US20020077491A1

  公开（公告）日：2002-06-20

  The invention relates to methods for forming combinatorial libraries. The invention provides methods suitable for the rapid and convenient synthesis of very large combinatorial libraries of small organic molecules. In particular, the invention provides a method for forming combinatorial libraries combining amide bond formation with epoxide opening.

  这项发明涉及形成组合库的方法。该发明提供了适用于快速和便捷合成非常大的小有机分子组合库的方法。具体而言，该发明提供了一种将酰胺键形成与环氧化物开启相结合的组合库形成方法。
• [EN] GLUCOSE-SENSITIVE PEPTIDE HORMONES<br/>[FR] HORMONES PEPTIDIQUES SENSIBLES AU GLUCOSE
  申请人：GUBRA APS

  公开号：WO2018115462A1

  公开（公告）日：2018-06-28

  The present invention relates to a conjugate of the formula P-L-I, wherein P is a peptide hormone effecting the metabolism of carbohydrates in vivo, L is a hydrolysable linker molecule consisting of Lp and Li, and I is a molecule capable of inhibiting the effect of the peptide hormone P on the metabolism of carbohydrates in vivo. Under in vivo conditions, the conjugate is the major compound. When the concentration of glucose increases in vivo, the concentration of the peptide hormone effecting the metabolism of carbohydrates in vivo also increases.

  本发明涉及一种公式为P-L-I的结合物，其中P是一种肽激素，在体内影响碳水化合物代谢，L是由Lp和Li组成的可水解连接分子，I是一种能够抑制肽激素P对体内碳水化合物代谢影响的分子。在体内条件下，该结合物是主要化合物。当体内葡萄糖浓度增加时，影响碳水化合物代谢的肽激素浓度也会增加。
• Synthesis of New Sulfated and Glucuronated Metabolites of Dietary Phenolic Compounds Identified in Human Biological Samples
  作者：A. Filipa Almeida、Cláudia N. Santos、M. Rita Ventura

  DOI：10.1021/acs.jafc.6b05629

  日期：2017.8.9

  standards has hampered the study of metabolite bioactivity and the exact structural confirmation in biological samples. New (poly)phenol metabolites previously identified in human samples after the intake of berry juice were chemically synthesized. Efficient chemical reactions were performed with moderate to excellent yields and selectivities. These new compounds could be used as standard chemicals

  （多）酚是水果和蔬菜中的一大类饮食化合物；它们的食用与有益健康有关。摄入后，（多）苯酚遭受广泛的代谢，其代谢产物的鉴定是一个新兴领域，因为这些代谢产物被认为是人类有机体中有效的生物活性分子。然而，缺乏可商购的标准阻碍了代谢物生物活性的研究以及生物样品中确切的结构确认。摄入浆果汁后，先前在人体样品中鉴定出的新的（多）苯酚代谢物是化学合成的。以中等至极好的产率和选择性进行了有效的化学反应。
• Novel and potent inhibitors of stearoyl-CoA desaturase-1. Part I: Discovery of 3-(2-hydroxyethoxy)-4-methoxy-N-[5-(3-trifluoromethylbenzyl)thiazol-2-yl]benzamide
  作者：Yoshikazu Uto、Tsuneaki Ogata、Jun Harada、Yohei Kiyotsuka、Yuko Ueno、Yuriko Miyazawa、Hitoshi Kurata、Tsuneo Deguchi、Nobuaki Watanabe、Toshiyuki Takagi、Satoko Wakimoto、Ryo Okuyama、Manabu Abe、Nobuya Kurikawa、Sayako Kawamura、Michiko Yamato、Jun Osumi

  DOI：10.1016/j.bmcl.2009.05.119

  日期：2009.8

  A series of structurally novel stearoyl-CoA desaturase-1 (SCD-1) inhibitors has been identified by optimizing a hit from our corporate library. Preliminary structure-activity relationship (SAR) studies led to the discovery of the highly potent and orally bioavailable thiazole-based SCD-1 inhibitor, 3-(2-hydroxyethoxy)-4-methoxy-N-[5-(3-trifluoromethylbenzyl)thiazol-2-yl]benzamide (23a). (C) 2009 Elsevier Ltd. All rights reserved.
• GLUCOSE-SENSITIVE PEPTIDE HORMONES
  申请人：Gubra ApS

  公开号：EP3558383A1

  公开（公告）日：2019-10-30