4-羟基-2,6-二甲基-苯甲酸甲酯 | 83194-70-1

• 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: 4-羟基-2,6-二甲基-苯甲酸甲酯
• 英文名称: methyl 4-hydroxy-2,6-dimethylbenzoate
• 英文别名: methyl 2,6-dimethyl-4-hydroxybenzoate
• CAS: 83194-70-1
• 化学式: C₁₀H₁₂O₃
• 分子量: 180.203
• InChiKey: QCXIFBNFVHBKCI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 储存条件：
  存于室温下，保持干燥并密封保存。

反应信息

• 作为反应物：
  描述：

  4-羟基-2,6-二甲基-苯甲酸甲酯 在 caesium carbonate 、 sodium hydroxide 作用下， 以 1,4-二氧六环 、 乙二醇乙醚 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 2,6-dimethyl-4-{[(2S)-4-methyl-3,4-dihydro-2H-1,4-benzoxazin-2-yl]methoxy}benzoic acid
  参考文献：
  名称：

  Discovery of new orally active prostaglandin D2 receptor antagonists

  摘要：

  To identify an orally available drug candidate, a series of 3-benzoylaminophenylacetic acids were synthesized and evaluated as prostaglandin D-2 (PGD(2)) receptor antagonists. Some of the compounds tested were found to exhibit excellent inhibitory activity against cAMP accumulation in human platelet rich plasma (hPRP), which is one of the indexes of DP antagonism. The optimization process including improvement of the physicochemical properties such as solubility, which may result in an improved pharmacokinetic (PK) profile, is presented. Optimized compounds were studied for their pharmacokinetics and in vivo potential. A structure-activity relationship study is also presented. Some of the test compounds were found to have in vivo efficacy towards the inhibition of PGD(2)-induced and OVA-induced vascular permeability in guinea pig conjunctiva. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.08.065
• 作为产物：
  描述：

  2,6-二甲基-4-氧代-2-环己烯-1-羧酸甲酯 在 碘 、 盐酸 作用下， 以 叔丁醇 、 水 为溶剂， 反应 72.0h， 以60%的产率得到4-羟基-2,6-二甲基-苯甲酸甲酯
  参考文献：
  名称：

  使用哈格曼酯制备高度官能化的酚类和苯类

  摘要：

  哈格曼酯可以转化为高度官能化的酚类或芳烃。Hagemann 酯衍生物的系统功能化允许制备三和四烷基取代的苯酚或四、五和六烷基取代的苯。发现 Kotnis 的芳构化程序依赖于溶剂，并且发现 Suzuki 偶联对空间位阻敏感。Wittig 烯化和邻-克莱森反应是分别在 C-4 和/或 C-5 位置引入烷基取代基的可靠方法。酸促进的叔醇 46 脱水生成烯酮 47，然后选择性烷基化（参见 48）是新的。

  DOI：

  10.3998/ark.5550190.0011.410

文献信息

• 2-saccharinylmethyl aryl carboxylates useful as proteolytic enzyme
  申请人：Sterling Winthrop Inc.

  公开号：US05512589A1

  公开（公告）日：1996-04-30

  A compound having the formula: ##STR1## wherein Ar, R.sup.4 and R.sup.5 are defined herein have pharmaceutical utility as proteolytic enzyme inhibitors.

  具有以下化学式的化合物：##STR1## 其中Ar，R.sup.4和R.sup.5的定义如下，在药物上具有蛋白酶抑制剂的用途。
• Piperazine derivatives useful as CCR5 antagonists
  申请人：Schering Corporation

  公开号：US06391865B1

  公开（公告）日：2002-05-21

  The use of CCR5 antagonists of the formula or a pharmaceutically acceptable salt thereof, wherein R is optionally substituted phenyl, pyridyl, thiophenyl or naphthyl; R1 is hydrogen or alkyl; R2 is substituted phenyl, substituted heteroaryl, naphthyl, fluorenyl, diphenylmethyl or optionally substituted phenyl- or heteroaryl-alkyl; R3 is hydrogen, alkyl, alkoxyalkyl, cycloalkyl, cycloalkylalkyl, or optionally substituted phenyl, phenylalkyl, naphthyl, naphthylalkyl, heteroaryl or heteroarylalkyl; R4, R5 and R7 are hydrogen or alkyl; R6 is hydrogen, alkyl or alkenyl; for the treatment of HIV, solid organ transplant rejection, graft v. host disease, arthritis, rheumatoid arthritis, inflammatory bowel disease, atopic dermatitis, psoriasis, asthma, allergies or multiple sclerosis is disclosed, as well as novel compounds, pharmaceutical compositions comprising them, and the combination of CCR5 antagonists of the invention in combination with antiviral agents useful in the treatment of HIV or agents useful in the treatment of inflammatory diseases.

  公开了使用CCR5拮抗剂的公式，其中 R是可选择的取代苯基，吡啶基，噻吩基或萘基; R1是氢或烷基; R2是取代苯基，取代杂环基，萘基，芴基，二苯甲基或可选择的取代苯基或杂环基烷基; R3是氢，烷基，烷氧基烷基，环烷基，环烷基烷基，或可选择的取代苯基，苯基烷基，萘基，萘基烷基，杂环基或杂环基烷基; R4，R5和R7是氢或烷基; R6是氢，烷基或烯基; 用于治疗HIV，固体器官移植排斥，移植物宿主病，关节炎，类风湿关节炎，炎症性肠病，特应性皮炎，牛皮癣，哮喘，过敏或多发性硬化症的方法，以及包含它们的新化合物，包含它们的药物组合物，以及CCR5拮抗剂与抗HIV治疗中有用的抗病毒剂或与治疗炎症性疾病中有用的药物的组合。
• [EN] COMPOUNDS AND METHODS FOR REGULATING INSULIN SECRETION<br/>[FR] COMPOSÉS ET MÉTHODES DE RÉGULATION DE SÉCRÉTION D'INSULINE
  申请人：BROAD INST INC

  公开号：WO2018175324A1

  公开（公告）日：2018-09-27

  Disclosed herein are methods for inducing insulin secretion in a glucose-dependent manner and compounds for use in these methods.

  本文揭示了一种在葡萄糖依赖性方式下诱导胰岛素分泌的方法以及用于这些方法的化合物。
• [EN] NEW BENZIMIDAZOLE DERIVATIVES<br/>[FR] NOUVEAUX DÉRIVÉS DE BENZIMIDAZOLE
  申请人：HOFFMANN LA ROCHE

  公开号：WO2010028981A1

  公开（公告）日：2010-03-18

  The invention is concerned with novel benzimidazole derivatives of Formula (I) wherein A, n and R1 to R7 are as defined in the description and in the claims, as well as physiologically acceptable salts and esters thereof. These compounds act on Farnesyl X receptor (FXR) and against cholesterol and lipid illnesses, diabetes, obesity, psoriasis, cancer, osteoporosis, Parkinson's and Alzheimer's disease.

  这项发明涉及一种新型苯并咪唑衍生物，其化学式为（I），其中A、n以及R1至R7如描述和索赔中所定义，以及其生理上可接受的盐和酯。这些化合物对法尼酰X受体（FXR）起作用，对抗胆固醇和脂质疾病、糖尿病、肥胖症、牛皮癣、癌症、骨质疏松症、帕金森病和阿尔茨海默病具有作用。
• [EN] ROMATIC COMPOUNDS AND PHARMACEUTICAL USES THEREOF<br/>[FR] COMPOSÉS AROMATIQUES ET LEURS UTILISATIONS PHARMACEUTIQUES
  申请人：BASF AS

  公开号：WO2020074964A1

  公开（公告）日：2020-04-16

  The present disclosure relates to compounds of the general formula (I): wherein R1, R2, R3, R4, R5, R6, and R7 may be chosen from different substituents; n is 0, 1, or 2; and X is a hydroxymethyl or a carboxylic acid or a derivative thereof, such as a carboxylate, such as a carboxylic ester, a glyceride, an anhydride, a phospholipid, a carboxamide, a phospholipid, or a prodrug thereof; or a pharmaceutically acceptable salt, solvate, solvate of such salt or a prodrug thereof. The present disclosure also relates to pharmaceutical compositions and lipid compositions comprising at least one compound according to the present disclosure, and to such compounds for use as medicaments or for use in therapy, in particular for the treatment of diseases related to metabolic diseases and liver diseases, such as non-alcoholic fatty liver disease and cholestasis diseases.

  本公开涉及一般式(I)的化合物：其中R1、R2、R3、R4、R5、R6和R7可以选择不同的取代基；n为0、1或2；X为羟甲基或羧酸或其衍生物，例如羧酸盐，如羧酸酯，甘油酯，酐，磷脂，羧酰胺，磷脂或其前药；或者为药用盐、溶剂化合物、该盐的溶剂化合物或其前药。本公开还涉及包含至少一种根据本公开的化合物的药物组合物和脂质组合物，以及这些化合物用作药物或用于治疗，特别是用于治疗与代谢疾病和肝病相关的疾病，如非酒精性脂肪肝病和胆汁淤积疾病。