1-benzyl-3-[(o-fluorophenyl)-(1-pyrryl)methyl]-3-pyrrolidinol | 79227-66-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-benzyl-3-[(o-fluorophenyl)-(1-pyrryl)methyl]-3-pyrrolidinol
• 英文别名: 1-Benzyl-3-[(2-fluorophenyl)-pyrrol-1-ylmethyl]pyrrolidin-3-ol
• CAS: 79227-66-0
• 化学式: C₂₂H₂₃FN₂O
• 分子量: 350.436
• InChiKey: ODRNECDKHVEXRV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  28.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-benzyl-3-[(o-fluorophenyl)-(1-pyrryl)methyl]-3-pyrrolidinol 在 sodium hydride 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 23.0h， 生成 rac-ethyl (2R,3R)-3-(1H-pyrrol-1-yl)-3H-spiro[benzofuran-2,3'-pyrrolidine]-1'-carboxylate
  参考文献：
  名称：

  2,3-Dihydro-3-(1-pyrryl)spiro[benzofuran-2,4'-piperidine]s and 2,3-dihydro-3-(1-pyrryl)spiro[benzofuran-2,3'-pyrrolidine]s: novel antihypertensive agents

  摘要：

  A series of 2,3-dihydro-3-(1-pyrryl)spiro[benzofuran-2,4'-piperidine]s (IV) and 2,3-dihydro-3-(1-pyrryl)spiro[benzofuran-2,3'-pyrrolidine]s (V) was synthesized and evaluated for cardiovascular activity. The majority of the compounds displayed good antihypertensive activity in the spontaneous hypertensive rat model at 50 mg/kg po. Compounds 5 (2,3-dihydro-1'-methyl-3-(1-pyrryl)spiro[benzofuran-2,4'-piperidine] ) and 12a (2,3-dihydro-1'-ethyl-3-(1-pyrryl)-spiro[benzofuran-2,4'-piperidine] ) were selected for a more detailed cardiovascular evaluation in the renal hypertensive rat and for standard cardiovascular challenges in anesthetized dogs and the sinoaortic-deafferented dog.

  DOI：

  10.1021/jm00364a027
• 作为产物：
  描述：

  2-氟苄胺 在 正丁基锂 、 溶剂黄146 作用下， 反应 4.0h， 生成 1-benzyl-3-[(o-fluorophenyl)-(1-pyrryl)methyl]-3-pyrrolidinol
  参考文献：
  名称：

  2,3-Dihydro-3-(1-pyrryl)spiro[benzofuran-2,4'-piperidine]s and 2,3-dihydro-3-(1-pyrryl)spiro[benzofuran-2,3'-pyrrolidine]s: novel antihypertensive agents

  摘要：

  A series of 2,3-dihydro-3-(1-pyrryl)spiro[benzofuran-2,4'-piperidine]s (IV) and 2,3-dihydro-3-(1-pyrryl)spiro[benzofuran-2,3'-pyrrolidine]s (V) was synthesized and evaluated for cardiovascular activity. The majority of the compounds displayed good antihypertensive activity in the spontaneous hypertensive rat model at 50 mg/kg po. Compounds 5 (2,3-dihydro-1'-methyl-3-(1-pyrryl)spiro[benzofuran-2,4'-piperidine] ) and 12a (2,3-dihydro-1'-ethyl-3-(1-pyrryl)-spiro[benzofuran-2,4'-piperidine] ) were selected for a more detailed cardiovascular evaluation in the renal hypertensive rat and for standard cardiovascular challenges in anesthetized dogs and the sinoaortic-deafferented dog.

  DOI：

  10.1021/jm00364a027

文献信息

• Spiro[dihydrobenzofuran-piperidines and -pyrrolidines]
  申请人：Hoechst-Roussel Pharmaceuticals Inc.

  公开号：US04329464A1

  公开（公告）日：1982-05-11

  The invention relates to spiro[dihydrobenzofuran-piperidines and -pyrrolidines] of the formula ##STR1## wherein R is the hydrogen atom, alkyl, alkoxycarbonyl, phenoxycarbonyl, cyano, and alkyl, alkanoyl, aralkanoyl, hydroxyalkyl, benzoylalkyl, ##STR2## where p is an integer of 2 or 3 and R.sub.1 and R.sub.2 are the same or different and are hydrogen and alkyl; X is hydrogen and alkyl; Hal is a halogen and q is an integer of 0 or 1; m is an integer of 1 or 2, n is an integer of 1, 2 or 3, where the sum of m and n is 3 or 4; and the pharmaceutically acceptable acid addition salts thereof.

  该发明涉及式中R为氢原子、烷基、烷氧羰基、苯氧羰基、氰基、烷基、烷酰基、芳基烷酰基、羟基烷基、苯甲酰基烷基的螺[二氢苯并呋喃-哌啶和-吡咯烷]，其中p为2或3的整数，R1和R2是相同或不同的氢和烷基；X为氢和烷基；Hal为卤素，q为0或1的整数；m为1或2的整数，n为1、2或3的整数，其中m和n的和为3或4；以及其药用可接受的酸盐。
• US4268515A
  申请人：——

  公开号：US4268515A

  公开（公告）日：1981-05-19
• US4321385A
  申请人：——

  公开号：US4321385A

  公开（公告）日：1982-03-23
• US4329464A
  申请人：——

  公开号：US4329464A

  公开（公告）日：1982-05-11
• 2,3-Dihydro-3-(1-pyrryl)spiro[benzofuran-2,4'-piperidine]s and 2,3-dihydro-3-(1-pyrryl)spiro[benzofuran-2,3'-pyrrolidine]s: novel antihypertensive agents
  作者：Larry Davis、Marc N. Agnew、Richard C. Effland、Joseph T. Klein、Jan M. Kitzen、Mary A. Schwenkler

  DOI：10.1021/jm00364a027

  日期：1983.10

  A series of 2,3-dihydro-3-(1-pyrryl)spiro[benzofuran-2,4'-piperidine]s (IV) and 2,3-dihydro-3-(1-pyrryl)spiro[benzofuran-2,3'-pyrrolidine]s (V) was synthesized and evaluated for cardiovascular activity. The majority of the compounds displayed good antihypertensive activity in the spontaneous hypertensive rat model at 50 mg/kg po. Compounds 5 (2,3-dihydro-1'-methyl-3-(1-pyrryl)spiro[benzofuran-2,4'-piperidine] ) and 12a (2,3-dihydro-1'-ethyl-3-(1-pyrryl)-spiro[benzofuran-2,4'-piperidine] ) were selected for a more detailed cardiovascular evaluation in the renal hypertensive rat and for standard cardiovascular challenges in anesthetized dogs and the sinoaortic-deafferented dog.