3-Cyclopentylpropyl methanesulfonate | 197146-48-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: 3-Cyclopentylpropyl methanesulfonate
• CAS: 197146-48-8
• 化学式: C₉H₁₈O₃S
• 分子量: 206.306
• InChiKey: UBJYDSDQCTYWGA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  51.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-Cyclopentylpropyl methanesulfonate 在 sodium azide 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
• 作为产物：
  描述：

  3-环戊基丙酸 在 甲基叔丁基醚 、 dimethyl sulfide borane 、 三乙胺 作用下， 生成 3-Cyclopentylpropyl methanesulfonate
  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。
• Cyclic aminophenyl sulfamate derivative
  申请人：Takegawa Shigehiro

  公开号：US20060189625A1

  公开（公告）日：2006-08-24

  This invention provides cyclicamino-phenyl sulfamate derivatives represented by a formula wherein each of R 1 and R 2 stands for hydrogen or lower alkyl; each of R 3 and R 4 stands for hydrogen, halogen, cyano or the like; A stands for nitrogen or CH; B stands for CH 2 , SO 2 , CO, optionally substituted phenyl or the like; and R 5 stands for alkyl, phenyl, amino or the like, or salts thereof which exhibit excellent steroid sulfatase inhibitory activity and are useful for prevention or treatment of diseases associated with steroids such as estrogen, androgen and the like.

  本发明提供了一种循环氨基苯磺酰胺衍生物，其表示为以下式子： 其中，R1和R2中的每一个代表氢或低碳基；R3和R4中的每一个代表氢、卤素、氰或类似物；A代表氮或CH；B代表CH2、SO2、CO、可选取代的苯基或类似物；R5代表烷基、苯基、氨基或类似物，或其盐，具有出色的类固醇磺酸酶抑制活性，可用于预防或治疗与雌激素、雄激素等类固醇相关的疾病。
• CYCLIC AMINOPHENYL SULFAMATE DERIVATIVE
  申请人：ASKA Pharmaceutical Co., Ltd.

  公开号：EP1627871B1

  公开（公告）日：2010-04-14
• US5705653A
  申请人：——

  公开号：US5705653A

  公开（公告）日：1998-01-06
• US7449466B2
  申请人：——

  公开号：US7449466B2

  公开（公告）日：2008-11-11