1-(cyclopentyl)-3-propylazide | 197146-49-9

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 英文名称: 1-(cyclopentyl)-3-propylazide
• 英文别名: (3-Azidopropyl)cyclopentane；3-azidopropylcyclopentane
• CAS: 197146-49-9
• 化学式: C₈H₁₅N₃
• 分子量: 153.227
• InChiKey: KTRBQCKIRKESTA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  11
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  14.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(cyclopentyl)-3-propylazide 在 dimethyl sulfide borane 、 硫酸 、 碳酸氢钠 作用下， 以 四氢呋喃 、 正辛烷 、 水 、 乙酸乙酯 为溶剂， 反应 48.0h， 生成 4-[4-(3-环戊基丙基)-5-羰基-4,5-二氢-1H-四唑-1-基]-N-[4-[2-[2(R)-羟基-2-(3-吡啶基)乙胺基]乙基]苯基]苯磺酰胺
  参考文献：
  名称：

  Practical chemoenzymatic synthesis of a 3-pyridylethanolamino β3 adrenergic receptor agonist

  摘要：

  A chemoenzymatic synthesis of beta(3) agonist 1 suitable for large scale preparation is described. The key chiral 3-pyridylethanolamine intermediate (R)-7 was prepared via an improved Neber rearrangement and a yeast-mediated asymmetric reduction. The tetrazolone fragment of the molecule was constructed via a dipolar cycloaddition between 1-(cyclopentyl)-3-propylazide and p-chlorosulfonyl phenylisocyanate. Sulfonamide coupling of these two intermediates under Shotten-Baumann conditions, followed by a borane reduction of the amide afforded 1 in 20-32% overall yield from 3-acetylpyridine, (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)01353-2
• 作为产物：
  描述：

  3-环戊基丙酸 在 sodium azide 、 甲基叔丁基醚 、 dimethyl sulfide borane 、 三乙胺 作用下， 以 二甲基亚砜 为溶剂， 生成 1-(cyclopentyl)-3-propylazide
  参考文献：
  名称：

  Practical chemoenzymatic synthesis of a 3-pyridylethanolamino β3 adrenergic receptor agonist

  摘要：

  A chemoenzymatic synthesis of beta(3) agonist 1 suitable for large scale preparation is described. The key chiral 3-pyridylethanolamine intermediate (R)-7 was prepared via an improved Neber rearrangement and a yeast-mediated asymmetric reduction. The tetrazolone fragment of the molecule was constructed via a dipolar cycloaddition between 1-(cyclopentyl)-3-propylazide and p-chlorosulfonyl phenylisocyanate. Sulfonamide coupling of these two intermediates under Shotten-Baumann conditions, followed by a borane reduction of the amide afforded 1 in 20-32% overall yield from 3-acetylpyridine, (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)01353-2

文献信息

• [EN] PROCESS FOR THE PREPARATION OF A beta 3-AGONIST<br/>[FR] PROCEDE DE PREPARATION D'UN AGONISTE DE beta 3
  申请人：MERCK & CO., INC.

  公开号：WO1997034880A1

  公开（公告）日：1997-09-25

  (EN) 3-Cyclopentylpropylazide and $i(p)-chlorosulfonylphenyl-isocyanate undergo cycloaddition to form 1-cyclopropyl-4-($i(p)-chloro-sulfonylphenyl) tetrazone-5-one, a key intermediate in the synthesis of an important $g(b)3-agonist.(FR) 3-cyclopentylpropylazide et $i(p)-chlorosulfonylphényl-isocyanate subissent un apport cyclique, de sorte que du 1-cyclopropyle-4-($i(p)-chlorosulfonylphényle)tétrazone-5-one soit produit, intermédiaire indispensable dans la synthèse d'un agoniste important de $g(b)3.

  3-环戊基丙基叠氮化物和$p$-氯磺酰基苯基异氰酸酯发生环加成反应，形成1-环丙基-4-($p$-氯磺酰基苯基)四唑-5-酮，是合成重要的$g(b)3-激动剂的关键中间体。
• US5705653A
  申请人：——

  公开号：US5705653A

  公开（公告）日：1998-01-06
• [EN] SULFAMOYL-CONTAINING DERIVATIVES AND USES THEREOF<br/>[FR] Dérivés contenant un sulfamoyle et leurs utilisations
  申请人：WYETH CORP

  公开号：WO2008049105A2

  公开（公告）日：2008-04-24

  [EN] Sulfamoyl-containing compounds are disclosed, having utility as inhibitors of disease-related targets, such as Heat Shock Protein 90 (HSP90), and which are useful for treating disorders, e.g., proliferative disorders, including HSP90-mediated disorders. Methods for preparing and using the disclosed compounds are also described.
  [FR] La présente invention concerne des composés contenant un sulfamoyle, présentant une utilité en tant qu'inhibiteurs de cibles liées à des maladies, comme la protéine de choc thermique 90 (HSP90), et utiles dans le traitement de troubles, par exemple de troubles prolifératifs, incluant les troubles induits par la HSP90. L'invention concerne également des procédés de préparation et d'utilisation des composés présentés.
• Practical chemoenzymatic synthesis of a 3-pyridylethanolamino β3 adrenergic receptor agonist
  作者：John Y.L Chung、Guo-Jie Ho、Michel Chartrain、Chris Roberge、Dalian Zhao、John Leazer、Roger Farr、Michael Robbins、Kateeta Emerson、David J Mathre、James M McNamara、David L Hughes、Edward J.J Grabowski、Paul J Reider

  DOI：10.1016/s0040-4039(99)01353-2

  日期：1999.9

  A chemoenzymatic synthesis of beta(3) agonist 1 suitable for large scale preparation is described. The key chiral 3-pyridylethanolamine intermediate (R)-7 was prepared via an improved Neber rearrangement and a yeast-mediated asymmetric reduction. The tetrazolone fragment of the molecule was constructed via a dipolar cycloaddition between 1-(cyclopentyl)-3-propylazide and p-chlorosulfonyl phenylisocyanate. Sulfonamide coupling of these two intermediates under Shotten-Baumann conditions, followed by a borane reduction of the amide afforded 1 in 20-32% overall yield from 3-acetylpyridine, (C) 1999 Elsevier Science Ltd. All rights reserved.