USDA 19 | 178483-00-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: USDA 19
• 英文别名: 3-(1-Propyl-pyrrolidin-3-yl)-phenol；3-(1-propylpyrrolidin-3-yl)phenol
• CAS: 178483-00-6
• 化学式: C₁₃H₁₉NO
• 分子量: 205.3
• InChiKey: WPYVGSUSOOZONM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  23.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  三氟甲磺酸酐 、 USDA 19 以84%的产率得到Trifluoro-methanesulfonic acid 3-(1-propyl-pyrrolidin-3-yl)-phenyl ester; hydrochloride
  参考文献：
  名称：

  Regioselective synthesis of 3-aryl substituted pyrrolidines via palladium catalyzed arylation: pharmacological evaluation for central dopaminergic and serotonergic activity.

  摘要：

  A series of 3-arylpyrrolidines has been synthesised via palladium catalyzed arylation and evaluated for dopaminergic and serotonergic activity in vitro and in vivo. Compounds substituted by electron withdrawing groups on the meta position of the aromatic ring, were found to be preferential dopamine autoreceptor antagonists. (C) 1997, Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(96)00618-x
• 作为产物：
  描述：

  3-(3-methoxyphenyl)-1-propylpyrrolidine 在 氢溴酸 作用下， 生成 USDA 19
  参考文献：
  名称：

  Regioselective synthesis of 3-aryl substituted pyrrolidines via palladium catalyzed arylation: pharmacological evaluation for central dopaminergic and serotonergic activity.

  摘要：

  A series of 3-arylpyrrolidines has been synthesised via palladium catalyzed arylation and evaluated for dopaminergic and serotonergic activity in vitro and in vivo. Compounds substituted by electron withdrawing groups on the meta position of the aromatic ring, were found to be preferential dopamine autoreceptor antagonists. (C) 1997, Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(96)00618-x

文献信息

• New phenyl-azacycloalkanes, processes for preparation and pharmaceutical preparations for such compounds
  申请人：Astra Läkemedel Aktiebolag

  公开号：EP0030526A1

  公开（公告）日：1981-06-17

  Compounds of the formula wherein n is 1 or 2, Y is OH, R'COO-, R2R3NCOO- or R4O whereby R1 is an alkyl group, or a possibly substituted phenyl group, R2 is an alkyl, phenethyl, benzyl or phenyl group, R3 is H or an alkyl group and R4 is an allyl or benzyl group, and R is an alkyl, hydroxyalkyl, dimethylaminoalkyl or methylthioalkyl group or alkenyl group, processes for their preparation and pharmaceutical preparations and methods of treatment employing such compounds. The compounds are useful for therapeutic purposes, especially for treatment of disorders in the central nervous system.

  式中化合物 其中 n 是 1 或 2，Y 是 OH、R'COO-、R2R3NCOO- 或 R4O 其中 R1 是烷基或可能取代的苯基，R2 是烷基、苯乙基、苄基或苯基，R3 是 H 或烷基，R4 是烯丙基或苄基，R 是烷基、羟基烷基、二甲基氨基烷基或甲硫基烷基或烯基，其制备工艺和药物制剂以及使用此类化合物的治疗方法。这些化合物可用于治疗目的，特别是治疗中枢神经系统疾病。
• New compounds useful as intermediates or starting materials for preparation of therapeutically useful phenyl-azacycloalkanes
  申请人：Carlsson, Per Arvid Emil

  公开号：EP0084920A2

  公开（公告）日：1983-08-03

  Compounds of the formula wherein Z3 is R or R6CO, wherein R is an alkyl group having 1-5 carbon atoms, a hydroxyalkyl, dimethylaminoalkyl or methylthioalkyl group having 2-6 carbon atoms in the alkyl part and having the heteroatom bound in a position other than 1-position, an alkenyl group having 3-5 carbon atoms other than an 1- alkenyl group, and R6 is an alkyl or alkoxy group containing 1-4 carbon atoms or an alkenyl group with 2-4 carbon atoms, R is an alkyl group with 1-5 carbon atoms, an allyl or benzyl group, and n is 1 or 2 provided that Z3 is other than methyl and ethyl when n is 2 and R7 is CH3 or an acid addition salt thereof. The compounds are useful as intermediates or starting materials for preparation of therapeutically useful substituted phenyl-azacycloalkanes.

  式中的化合物 其中 Z3 是 R 或 R6CO，其中 R 是含有 1-5 个碳原子的烷基、烷基部分含有 2-6 个碳原子且杂原子结合在 1 位以外位置的羟基烷基、二甲基氨基烷基或甲基硫代烷基、含有 3-5 个碳原子的烯基（1-烯基除外）、R6 是含有 1-4 个碳原子的烷基或烷氧基，或含有 2-4 个碳原子的烯基，R 是含有 1-5 个碳原子的烷基、烯丙基或苄基，n 是 1 或 2，条件是当 n 为 2 时，Z3 不是甲基和乙基，R7 是 CH3 或其酸加成盐。这些化合物可作为中间体或起始原料，用于制备对治疗有用的取代苯基氮杂环烷烃。
• US4426386A
  申请人：——

  公开号：US4426386A

  公开（公告）日：1984-01-17
• [EN] NEW PHENYL-AZACYCLOALKANES
  申请人：——

  公开号：WO1981001552A1

  公开（公告）日：1981-06-11

  (EN) Compounds of the formula: (FORMULA) wherein n is 1 or 2, Y is OH, R1C00-, R2R3NC00- or R40 whereby R1 is an alkyl group, or a possibly substituted phenyl group, R2 is an alkyl, phenethyl, benzyl or phenyl group, R3 is H or an alkyl group and R4 is an allyl or benzyl group, and R is an alkyl, hydroxyalkyl, dimethylaminoalkyl or methylthioalkyl group or alkenyl group, processes for their preparation and pharmaceutical preparations and methods of treatment employing such compounds. The compounds are useful for therapeutic purposes, especially for treatment of disorders in the central nervous system. (FR) Composes de formule (FORMULE) ou n est egal a 1 ou 2, Y represente 0H, R1 COO-, R2R3NCOO- ou R4O, ou R1 est un groupe alkyle, ou eventuellement un groupe phenyle substitue, R2 est un groupe alkyle, phenethyle, benzyle ou phenyle, R3 represente H ou un groupe alkyle et R4 represente un groupe allyle ou benzyle, et R represente un groupe alkyle, hydroxyalkyle, dimethylaminoalkyle ou methylethioalkyle ou un groupe alkenyle, leurs procedes de preparation et preparations pharmaceutiques et methode de traitement utilisant ces composes. Les composes sont utiles a des usages therapeutiques, specialement pour le traitement de troubles du systeme nerveux.
• Regioselective synthesis of 3-aryl substituted pyrrolidines via palladium catalyzed arylation: pharmacological evaluation for central dopaminergic and serotonergic activity.
  作者：Clas Sonesson、Håkan Wikström、Martin W Smith、Kjell Svensson、Arvid Carlsson、Nicholas Waters

  DOI：10.1016/s0960-894x(96)00618-x

  日期：1997.2

  A series of 3-arylpyrrolidines has been synthesised via palladium catalyzed arylation and evaluated for dopaminergic and serotonergic activity in vitro and in vivo. Compounds substituted by electron withdrawing groups on the meta position of the aromatic ring, were found to be preferential dopamine autoreceptor antagonists. (C) 1997, Elsevier Science Ltd.