甲基4-(3-羟基-2-甲基丙基)苯甲酸酯 | 170955-21-2

• 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: 甲基4-(3-羟基-2-甲基丙基)苯甲酸酯
• 中文别名: 2-氯丁-3-烯-1-醇
• 英文名称: 3-(4-methoxycarbonyl)phenyl-2-methyl-1-propanol
• 英文别名: Methyl 4-(3-hydroxy-2-methylpropyl)benzoate
• CAS: 170955-21-2
• 化学式: C₁₂H₁₆O₃
• 分子量: 208.257
• InChiKey: BANBEJVSLPOVCM-UHFFFAOYSA-N

物化性质

• 沸点：
  334.1±25.0 °C(Predicted)
• 密度：
  1.090±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 甲基4-(3-羟基-2-甲基丙基)苯甲酸酯 以 吡啶 为溶剂， 反应 4.5h， 以89%的产率得到3-(4-methoxycarbonyl)phenyl-2-methylprop-1-yl acetate
  参考文献：
  名称：

  A chemo-enzymatic approach to optically active 3-(4-methoxycarbonyl)phenyl-2-methyl-1-propanols

  摘要：

  With a view to obtaining both enantiomers of 3-(4-methoxycarbonyl)phenyl-2-methyl-1-propanols, (R)-1 and (S)-1, from the respective racemate, (+/-)-1, the hydrolysis of its acetate, (+/-)-2, in the presence of porcine pancreatic lipase (PPL) has been studied. The optical puriry of (R)-1 and (S)-1 thus obtained was unsatisfactory (ee 22-27 %), and could not be increased beyond ee 33 % by repeated enzymatic hydrolysis of the unconverted fraction of the acetate. In contrast with this, the biohydrogenation of 3-(4-methoxycarbonyl)phenyl-2-methyl-2-propen-1-ol (4) with fermenting Saccharomyces cerevisiae afforded (S)-1 of considerably higher optical purity (ee 41-90 %, depending on the strain). The stereochemical correlation of the products obtained in the two biochemical processes under study shows that the PPL-catalyzed hydrolysis of (+/-)-2 produces preferably (R)-1.

  DOI：

  10.1007/bf00698514
• 作为产物：
  描述：

  Methyl 4-(2-methyl-3-oxoprop-1-en-1-yl)benzoate 在 palladium on activated charcoal sodium tetrahydroborate 、 氢气 作用下， 以 甲醇 为溶剂， 反应 52.0h， 生成 甲基4-(3-羟基-2-甲基丙基)苯甲酸酯
  参考文献：
  名称：

  A chemo-enzymatic approach to optically active 3-(4-methoxycarbonyl)phenyl-2-methyl-1-propanols

  摘要：

  With a view to obtaining both enantiomers of 3-(4-methoxycarbonyl)phenyl-2-methyl-1-propanols, (R)-1 and (S)-1, from the respective racemate, (+/-)-1, the hydrolysis of its acetate, (+/-)-2, in the presence of porcine pancreatic lipase (PPL) has been studied. The optical puriry of (R)-1 and (S)-1 thus obtained was unsatisfactory (ee 22-27 %), and could not be increased beyond ee 33 % by repeated enzymatic hydrolysis of the unconverted fraction of the acetate. In contrast with this, the biohydrogenation of 3-(4-methoxycarbonyl)phenyl-2-methyl-2-propen-1-ol (4) with fermenting Saccharomyces cerevisiae afforded (S)-1 of considerably higher optical purity (ee 41-90 %, depending on the strain). The stereochemical correlation of the products obtained in the two biochemical processes under study shows that the PPL-catalyzed hydrolysis of (+/-)-2 produces preferably (R)-1.

  DOI：

  10.1007/bf00698514

文献信息

• [EN] GLUCAGON RECEPTOR ANTAGONISTS, PREPARATION AND THERAPEUTIC USES<br/>[FR] ANTAGONISTE DES RECEPTEURS DU GLUCAGON, PREPARATION ET UTILISATIONS THERAPEUTIQUES
  申请人：LILLY CO ELI

  公开号：WO2005123668A1

  公开（公告）日：2005-12-29

  The present invention discloses novel compounds of Formula I, or pharmaceutically acceptable salts thereof, which have glucagon receptor antagonist or inverse agonist activity, as well as methods for preparing such compounds. In another embodiment, the invention discloses pharmaceutical compositions comprising compounds of Formula I as well as methods of using them to treat diabetic and other glucagon related metabolic disorders, and the like.

  本发明公开了具有胰高血糖素受体拮抗剂或逆拮抗剂活性的化合物I的新化合物，或其药用可接受的盐，以及制备这些化合物的方法。在另一实施例中，本发明公开了包含化合物I的药物组合物，以及使用它们治疗糖尿病和其他与胰高血糖素相关的代谢性疾病等方法。
• GLUCAGON RECEPTOR ANTAGONISTS, PREPARATION AND THERAPEUTIC USES
  申请人：ELI LILLY AND COMPANY

  公开号：EP1758853A1

  公开（公告）日：2007-03-07
• [EN] GLUCAGON RECEPTOR ANTAGONISTS, PREPARATION AND THERAPEUTIC USES<br/>[FR] ANTAGONISTES DE RÉCEPTEUR DU GLUCAGON, PROCÉDÉS DE PRÉPARATION ET UTILISATIONS THÉRAPEUTIQUES
  申请人：LILLY CO ELI

  公开号：WO2007120270A2

  公开（公告）日：2007-10-25

  [EN] The present invention discloses novel compounds of Formula (I), or pharmaceutically acceptable salts thereof, which have glucagon receptor antagonist or inverse agonist activity, as well as methods for preparing such compounds. In another embodiment, the invention discloses pharmaceutical compositions comprising compounds of Formula (I) as well as methods of using them to treat diabetic and other glucagon related metabolic disorders, and the like.
  [FR] La présente invention concerne de nouveaux composés de formule (I) ou des sels de ceux-ci, acceptables d'un point de vue pharmaceutique, qui présentent une activité d'agoniste inverse ou d'antagoniste de récepteur du glucagon, ainsi que des procédés de préparation de tels composés. Dans d'autres modes de réalisation, cette invention concerne des compositions pharmaceutiques comprenant des composés de formule (I), ainsi que des procédés d'utilisation de ceux-ci pour traiter des troubles diabétiques, d'autres troubles métaboliques liés au glucagon et des troubles similaires.
• A chemo-enzymatic approach to optically active 3-(4-methoxycarbonyl)phenyl-2-methyl-1-propanols
  作者：G. D. Gamalevich、A. V. Ignatenko、E. P. Serebryakov、N. E. Voishvillo

  DOI：10.1007/bf00698514

  日期：1995.4

  With a view to obtaining both enantiomers of 3-(4-methoxycarbonyl)phenyl-2-methyl-1-propanols, (R)-1 and (S)-1, from the respective racemate, (+/-)-1, the hydrolysis of its acetate, (+/-)-2, in the presence of porcine pancreatic lipase (PPL) has been studied. The optical puriry of (R)-1 and (S)-1 thus obtained was unsatisfactory (ee 22-27 %), and could not be increased beyond ee 33 % by repeated enzymatic hydrolysis of the unconverted fraction of the acetate. In contrast with this, the biohydrogenation of 3-(4-methoxycarbonyl)phenyl-2-methyl-2-propen-1-ol (4) with fermenting Saccharomyces cerevisiae afforded (S)-1 of considerably higher optical purity (ee 41-90 %, depending on the strain). The stereochemical correlation of the products obtained in the two biochemical processes under study shows that the PPL-catalyzed hydrolysis of (+/-)-2 produces preferably (R)-1.