N-isopropoxycarbonylimidazole | 82998-18-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: N-isopropoxycarbonylimidazole
• 英文别名: 1-isopropoxycarbonylimidazole；isopropyl 1-imidazolecarboxylate；isopropyl 1H-imidazole-1-carboxylate；imidazole-1-carboxylic acid isopropyl ester；propan-2-yl imidazole-1-carboxylate
• CAS: 82998-18-3
• 化学式: C₇H₁₀N₂O₂
• 分子量: 154.169
• InChiKey: UAILNBAKJABHNQ-UHFFFAOYSA-N

物化性质

• 密度：
  1.098 g/mL at 25 °C
• 闪点：
  108℃

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  44.1
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• WGK Germany：
  3
• 危险性防范说明：
  P261,P264,P270,P271,P280,P301+P312,P302+P352,P304+P340,P305+P351+P338,P330,P332+P313,P337+P313,P362,P403+P233,P405,P501
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  2-8°C，惰性气体

反应信息

• 作为反应物：
  描述：

  N-isopropoxycarbonylimidazole 在 一水合肼 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 肼基甲酸异丙酯
  参考文献：
  名称：

  N杂环取代基指示的芳烃与芳烃的钯催化氧化C–H烷氧基羰基化反应

  摘要：

  我们报告了一种环境友好的方案，用于芳烃的C–H烷氧基羰基化与由N-杂环取代基指示的烷基氨基甲酸酯。Pd（OAc）2用于催化这种氧化性自由基的羰基化转化。该反应可耐受多种官能团，从而以高收率和优异的区域选择性提供产物。

  DOI：

  10.1002/ejoc.202000530
• 作为产物：
  描述：

  咪唑 、 氯甲酸异丙酯 生成 N-isopropoxycarbonylimidazole
  参考文献：
  名称：

  On the reactivity of imidazole carbamates and ureas and their use as esterification and amidation reagents

  摘要：

  The optimization, substrate scope, and mechanism of esterification and amidation of carboxylic acids mediated by imidazole-based reagents are discussed. The innate reactivity of carbonylimidazole reagents with a range of nucleophiles is also explored. New reagents developed for the synthesis of alpha,beta-unsaturated esters are described, as are reagents for the preparation of tertiary amides directly from carboxylic acids. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.09.057

文献信息

• Photochemistry of <i>N-</i>Acetyl-, <i>N-</i>Trifluoroacetyl-, <i>N-</i> Mesyl-, and <i>N-</i>Tosyldibenzothiophene Sulfilimines
  作者：Vasumathi Desikan、Yonglin Liu、John P. Toscano、William S. Jenks

  DOI：10.1021/jo702654q

  日期：2008.6.1

  Time-resolved infrared (TRIR) spectroscopy, product studies, and computational methods were applied to the photolysis of sulfilimines derived from dibenzothiophene that were expected to release acetylnitrene, trifluoroacetylnitrene, mesylnitrene, and tosylnitrene. All three methods provided results for acetylnitrene consistent with literature precedent and analogous experiments with the benzoylnitrene

  时间分辨红外（TRIR）光谱，产品研究和计算方法被应用于对二苯并噻吩衍生的亚硫胺的光解，这些亚硫胺有望释放出乙炔，三氟乙炔，甲磺腈和甲苯磺腈。所有这三种方法均提供了乙炔基丁二烯的结果，该结果与文献中的先例和与苯甲酰基丁二烯前体的类似实验一致，即基态多重性为单峰。相比之下，尽管TRIR实验更加模糊，但产品研究清楚地表明了三氟乙酰基丁二烯的三重态反应性。产品研究表明，这些亚硫胺是磺酰氮的优良来源，与相应的叠氮化物相比，它们具有三重基态，并且计算研究为腈的电子结构提供了线索。
• A versatile method for preparation of O-alkylperoxycarbonic acids: epoxidation with alkyloxycarbonylimidazoles and hydrogen peroxide
  作者：Youko Tsunokawa、Shigeo Iwasaki、Shigenobu Okuda

  DOI：10.1016/s0040-4039(00)87275-5

  日期：1982.1

  A variety of O-alkylperoxycarbonic acids () were conveniently prepared by utilizing alkyloxycarbonylimidazoles () as their precursors. Epoxidation of alkenes with such peroxy-acids was studied and their reactivities were compared with those of peroxycarboxylic acids.

  通过使用烷氧基羰基咪唑（）作为前体可方便地制备各种O-烷基过氧碳酸（）。研究了用这种过氧酸对烯烃的环氧化，并将其反应性与过氧羧酸的反应性进行了比较。
• Chemoselective N-Acylation of Indoles and Oxazolidinones with Carbonylazoles
  作者：Stephen T. Heller、Erica E. Schultz、Richmond Sarpong

  DOI：10.1002/anie.201203976

  日期：2012.8.13

  Unique reactivity: In the presence of more reactive amine and alcohol functional groups and of carboxylic acids, the chemoselective N‐acylation of indoles (see scheme) and oxazolidinones is achieved by taking advantage of the unique reactivity of carbonylazole acylating agents with catalytic amounts of 1,8‐diazabicyclo[5.4.0]undec‐7‐ene (DBU).

  独特的反应性：在存在更多的反应性胺和醇官能团以及羧酸的情况下，吲哚和恶唑烷酮的化学选择性N-酰化是通过利用催化量为1的羰基唑酰化剂的独特反应性来实现的，8-二氮杂双环[5.4.0]十一月-7-烯（DBU）。
• [EN] 3-UREIDOISOQUINOLIN-8-YL DERIVATIVES<br/>[FR] DÉRIVÉS DE 3-URÉIDOISOQUINOLÉIN-8-YLE
  申请人：ACTELION PHARMACEUTICALS LTD

  公开号：WO2012131588A1

  公开（公告）日：2012-10-04

  The invention relates to 3-ureidoisoquinolin-8-yl derivatives of formula I I wherein R is alkyl, haloalkyl or cyclopropyl; R 2 is H, halogen, pyridazin-4-yl, pyrimidin-5-yl or an optionally substituted pyridin-3-yl, pyridin-4-yl or phenyl group; R 3 is alkyl, alkynyl, aminoalkyl, carbamoylalkyl, methylcarbamoylalkyl, alkoxy, haloalkoxy, alkynyloxy, (4-hydroxybut-2-yn-1-yl)oxy, (4-aminobut-2-yn-1-yl)oxy, dimethylaminoalkoxy, carbamoylalkoxy, alkylamino, cycloalkyl, cycloalkylalkyl, cycloalkylalkoxy, hydroxyalkyl, hydroxyalkoxy, alkoxyalkyl, alkoxyalkoxy, carboxyalkyl, carboxyalkoxy, alkoxycarbonylalkoxy, aryl, heteroaryl, benzyl, benzyloxy, 2-cyanoethoxy, 2,3-dihydroxypropoxy, 3,4-dihydroxybutoxy, -CH 2 R a, -CH 2 CH 2 R b, -(CH 2 ) n -C(O)O-R d, -(CH 2 ) n -N(R c )C(O)O-R d, -O-(CH 2 ) n -N(R c )C(O)O-R d, -(CH 2 ) n -R e or -O-(CH 2 ) n -R e; R a is cyano, acetylamino or N,N-dimethylamino; R b is cyano or carbamoyl; R c is H or methyl; R d is alkyl; R e is pyrrolidin-1-yl, piperidin-1-yl, piperidin-3-yl, morpholin-1-yl, 2-oxopyrrolidin-1-yl, 5-oxopyrrolidin-2-yl, 2,5-dioxopyrrolidin-1-yl, 2-oxoimidazolidin-1-yl, 4-(tert-butoxycarbonyl)piperazin-1-yl, 4-(aminomethyl)cyclohexyl or heteroaryl; R 4 is H or methyl; and to the salts of such compounds. These compounds are useful for the prevention or the treatment of bacterial infections.

  该发明涉及式I的3-脲基异喹啉-8-基衍生物，其中R为烷基、卤代烷基或环丙基；R2为H、卤素、吡啶并[4,5-d]嘧啶-4-基、嘧啶-5-基或可选择取代的吡啶-3-基、吡啶-4-基或苯基；R3为烷基、炔基、氨基烷基、氨基甲酰烷基、甲基氨基甲酰烷基、烷氧基、卤代烷氧基、炔基氧基、(4-羟基丁-2-炔-1-基)氧基、(4-氨基丁-2-炔-1-基)氧基、二甲胺基烷氧基、甲酰胺烷氧基、烷基氨基、环烷基、环烷基烷基、环烷基烷氧基、羟基烷基、羟基烷氧基、烷氧基烷基、烷氧基烷氧基、羧基烷基、羧基烷氧基、烷氧羰基烷氧基、芳基、杂环芳基、苄基、苄氧基、2-氰基乙氧基、2,3-二羟基丙氧基、3,4-二羟基丁氧基、- Ra、- Rb、-(CH2)n-C(O)O-Rd、-( )n-N(Rc)C(O)O-Rd、-O-( )n-N(Rc)C(O)O-Rd、-( )n-Re或-O-( )n-Re；Ra为氰基、乙酰氨基或N,N-二甲基氨基；Rb为氰基或甲酰基；Rc为H或甲基；Rd为烷基；Re为吡咯烷-1-基、哌啶-1-基、哌啶-3-基、吗啉-1-基、2-氧代吡咯烷-1-基、5-氧代吡咯烷-2-基、2,5-二氧代吡咯烷-1-基、2-氧代咪唑烷-1-基、4-(叔丁氧羰基)哌嗪-1-基、4-(氨甲基)环己基或杂环芳基；R4为H或甲基；以及这些化合物的盐。这些化合物对于预防或治疗细菌感染是有用的。
• [EN] MODULATORS OF THE GPR119 RECEPTOR AND THE TREATMENT OF DISORDERS RELATED THERETO<br/>[FR] MODULATEURS DU RÉCEPTEUR GPR119 ET TRAITEMENT DE TROUBLES ASSOCIÉS À CELUI-CI
  申请人：ARENA PHARM INC

  公开号：WO2012170702A1

  公开（公告）日：2012-12-13

  The present invention relates to compounds of Formula (Ia) and pharmaceutically acceptable salts, solvates, hydrates, and N-oxides thereof, that are useful as single pharmaceutical agents or in combination with one or more additional pharmaceutical agents, such as, an inhibitor of DPP-IV, a biguanide, an alpha-glucosidase inhibitor, an insulin analogue, a sulfonylurea, an SGLT2 inhibitor, a meglitinide, a thiazolidinedione, or an anti-diabetic peptide analogue, in the treatment of, for example, a disorder selected from: a GPR119-receptor-related disorder; a condition ameliorated by increasing secretion of an incretin; a condition ameliorated by increasing a blood incretin level; a condition characterized by low bone mass; a neurological disorder; a metabolic-related disorder; type 2 diabetes; obesity; and complications related thereto.

  本发明涉及具有式(Ia)的化合物以及其药学上可接受的盐、溶剂合物、水合物和N-氧化物，这些化合物可用作单一药物代理或与一个或多个额外的药物代理结合使用，例如DPP-IV的抑制剂、双胍类药物、α-葡萄糖苷酶抑制剂、胰岛素类似物、磺脲类药物、SGLT2抑制剂、麦格利那类药物、噻唑烷二酮或抗糖尿病肽类似物，在治疗中使用，例如选择自以下疾病的一种：GPR119受体相关疾病；通过增加肠高血糖素分泌改善的情况；通过增加血液高血糖素水平改善的情况；低骨量特征的情况；神经系统疾病；代谢相关疾病；2型糖尿病；肥胖及相关并发症。