2-(diethoxyphosphorylmethyl)-4,5-dihydro-1H-imidazole-1-carboxylic acid tert-butyl ester | 272110-34-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机膦酸及其衍生物
• 英文名称: 2-(diethoxyphosphorylmethyl)-4,5-dihydro-1H-imidazole-1-carboxylic acid tert-butyl ester
• 英文别名: 1-tert-butyloxycarbonyl-2-(diethylphosphomomethyl)-2-imidazoline；(Diethoxy-phosphorylmethyl)-4,5-dihydro-imidazole-1-carboxylic Acid Tert-Butyl Ester；Tert-butyl 2-(diethoxyphosphorylmethyl)-4,5-dihydroimidazole-1-carboxylate
• CAS: 272110-34-6
• 化学式: C₁₃H₂₅N₂O₅P
• 分子量: 320.326
• InChiKey: QUGBLLYIYKCEKU-UHFFFAOYSA-N

物化性质

• 沸点：
  398.5±44.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  21
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  77.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-Thienyl-3'-pyridyl ketone 、 2-(diethoxyphosphorylmethyl)-4,5-dihydro-1H-imidazole-1-carboxylic acid tert-butyl ester 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 以98%的产率得到
  参考文献：
  名称：

  Imidazolines as efficacious glucose-dependent stimulators of insulin secretion

  摘要：

  Synthesis of a series of imidazolines with glucose dependent effects on insulin exocytosis from pancreatic P-cells is reported. Regioisomers and enantionters were found to exhibit marked differences in exocytotic effects as well as different activities on the K-ATP-channel- the (R (+)) isomer of 2-[2-(4,5-dihydro-1H-imidazol-2-yl)-1-thiophene-2-ylethyl]pyridine (4a) and the (+) isomer of 2-[2-(4,5-dihydro-1H-imidazol-2-yl)-1-thiophene-3-yiethyl]pyridine (4d) were found to give a significant increase in insulin release in contrast to Findings for their enantiomers-without influence on the K-ATP-channel. The (+) isomer (4a) showed glucose dependent insulin release from P-cells at concentrations above 2.5 mM and a marked glucose lowering effect in ob/ob mice as well as in fed but not in fasted rats. (C) 2003 Editions scientifiques et medicales Elsevier SAS. All rights reserved.

  DOI：

  10.1016/s0223-5234(03)00041-2
• 作为产物：
  描述：

  氰甲基磷酸二乙酯 在 盐酸 、 三乙胺 作用下， 以 乙醚 、 乙醇 、 二氯甲烷 为溶剂， 反应 69.0h， 生成 2-(diethoxyphosphorylmethyl)-4,5-dihydro-1H-imidazole-1-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Imidazolines as efficacious glucose-dependent stimulators of insulin secretion

  摘要：

  Synthesis of a series of imidazolines with glucose dependent effects on insulin exocytosis from pancreatic P-cells is reported. Regioisomers and enantionters were found to exhibit marked differences in exocytotic effects as well as different activities on the K-ATP-channel- the (R (+)) isomer of 2-[2-(4,5-dihydro-1H-imidazol-2-yl)-1-thiophene-2-ylethyl]pyridine (4a) and the (+) isomer of 2-[2-(4,5-dihydro-1H-imidazol-2-yl)-1-thiophene-3-yiethyl]pyridine (4d) were found to give a significant increase in insulin release in contrast to Findings for their enantiomers-without influence on the K-ATP-channel. The (+) isomer (4a) showed glucose dependent insulin release from P-cells at concentrations above 2.5 mM and a marked glucose lowering effect in ob/ob mice as well as in fed but not in fasted rats. (C) 2003 Editions scientifiques et medicales Elsevier SAS. All rights reserved.

  DOI：

  10.1016/s0223-5234(03)00041-2

文献信息

• A New Protocol for the Synthesis of N(1)-Unsubstituted 2-Substituted 2-Imidazolines
  作者：Raymond C.F. Jones、Paschalis Dimopoulos

  DOI：10.1016/s0040-4020(00)00108-3

  日期：2000.3

  Lateral metallation at C-2(α) of 1-tert-butoxycarbonyl-2-methyl-2-imidazoline followed by reaction with a range of C-electrophiles and deprotection with TFA reliably affords N(1)-unsubstituted 2-substituted 2-imidazolines; P- or Se-electrophiles lead to 2-alkenyl-2-imidazolines via Wadsworth–Emmons or selenoxide elimination protocols.

  1-叔丁氧基羰基-2-甲基-2-咪唑啉在C-2（α）上的侧向金属化反应，然后与一系列C-亲电子试剂反应，并用TFA脱保护，可可靠地提供N（1）-未取代的2-取代的2-咪唑啉 P或Se亲电试剂通过Wadsworth-Emmons或亚硒酸盐消除方案生成2-烯基-2-咪唑啉。
• Oral hypoglycaemic agents
  申请人：——

  公开号：US20020132812A1

  公开（公告）日：2002-09-19

  Compounds of formula (I) which are optionally substituted 2-(&ohgr;,&ohgr;-diarylalkyl)-4,5-dihydro-1H-imidazoles and 2-(&ohgr;,&ohgr;-diarylalkyl)-1,4,5,6-tetrahydropyrimidines and salts thereof with inorganic and organic acids have interesting pharmacological properties. Thus, the compounds are useful in the treatment of type 2 diabetes.

  式(I)的化合物，它们是可选择取代的2-(&ohgr;，&ohgr;-二芳基烷基)-4,5-二氢-1H-咪唑和2-(&ohgr;，&ohgr;-二芳基烷基)-1,4,5,6-四氢嘧啶及其与无机和有机酸的盐具有有趣的药理特性。因此，这些化合物在治疗2型糖尿病方面是有用的。
• [EN] 1,3-DIAZAHETEROCYCLIC COMPOUNDS AND THEIR USE AS ORAL HYPOGLYCAEMIC AGENTS<br/>[FR] COMPOSES 1,3 DIAZHETEROCYCLIQUES ET UTILISATION DE CES DERNIERS COMME AGENTS HYPOGLYCEMIANTS
  申请人：NOVO NORDISK AS

  公开号：WO2002038559A1

  公开（公告）日：2002-05-16

  A compound of formula (I) wherein Y is selected from the ring systems (a), (b); R?1 and R2¿ are independently phenyl, naphthyl, thienyl, thiazolyl, imidazolyl, pyrazolyl, triazolyl, pyridyl, pyrimidyl, pyridazinyl, pyrazinyl, quinolyl, 3-4-dihydroquinolyl, 5,6,7,8-tetrahydroquinolyl, isoquinolyl, 3,4-dihydroisoquinolyl, 5,6,7,8-tetrahydroisoquinolyl, indolyl, benzo[b]thienyl, benzimidazozyl, 5,6,7,8-tetrahydroimidazo[1,5-a]pyridyl or benzthiazolyl each of which is optionally substituted. R?3 and R5¿ are independently hydrogen, C¿1-6? alkyl or halogen or when taken together R?3 and R5¿ form an additional bond between the carbon atoms which they are attached; R¿4? is hydrogen, C1-6alkyl, arylC1-6alkyl, C1-6-C(O)- or arylC1-6alkyl-C(O)-, X is -CR?18R19¿- wherein R?18 and R19¿ are independently hydrogen or C¿1-6?alkyl; n is 0, 1 or 2. Thus, the compounds are useful in the treatment of type 2 diabetes.
• Imidazolines as efficacious glucose-dependent stimulators of insulin secretion
  作者：P Jakobsen

  DOI：10.1016/s0223-5234(03)00041-2

  日期：2003.4

  Synthesis of a series of imidazolines with glucose dependent effects on insulin exocytosis from pancreatic P-cells is reported. Regioisomers and enantionters were found to exhibit marked differences in exocytotic effects as well as different activities on the K-ATP-channel- the (R (+)) isomer of 2-[2-(4,5-dihydro-1H-imidazol-2-yl)-1-thiophene-2-ylethyl]pyridine (4a) and the (+) isomer of 2-[2-(4,5-dihydro-1H-imidazol-2-yl)-1-thiophene-3-yiethyl]pyridine (4d) were found to give a significant increase in insulin release in contrast to Findings for their enantiomers-without influence on the K-ATP-channel. The (+) isomer (4a) showed glucose dependent insulin release from P-cells at concentrations above 2.5 mM and a marked glucose lowering effect in ob/ob mice as well as in fed but not in fasted rats. (C) 2003 Editions scientifiques et medicales Elsevier SAS. All rights reserved.