tert-butyl (2R)-2-[3-(2-hydroxy-5-oxopyrrolidin-1-yl)prop-1-ynyl]piperidine-1-carboxylate | 134441-64-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: tert-butyl (2R)-2-[3-(2-hydroxy-5-oxopyrrolidin-1-yl)prop-1-ynyl]piperidine-1-carboxylate
• CAS: 134441-64-8；134441-94-4
• 化学式: C₁₇H₂₆N₂O₄
• 分子量: 322.404
• InChiKey: OFSXVDITHQDZPF-KWCCSABGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  70.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  tert-butyl (2R)-2-[3-(2-hydroxy-5-oxopyrrolidin-1-yl)prop-1-ynyl]piperidine-1-carboxylate 在 三乙基硅烷 、 甲酸 、 三氟乙酸 作用下， 反应 2.0h， 生成 3-(2-oxo-1-pyrrolidinyl)-1-(N-methyl-2(R)-piperidinyl)-1-propyne
  参考文献：
  名称：

  Synthesis of chiral α-acetylenic cyclic amines from α-amino acids: Applications to differentially constrained oxotremorine analogues as muscarinic agents

  摘要：

  DOI：

  10.1016/s0040-4039(00)94471-x
• 作为产物：
  描述：

  3-hydroxy-1-<2(R)-<1-(tert-butoxycarbonyl)piperidinyl>>-1-propyne 在 sodium tetrahydroborate 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 0.75h， 生成 tert-butyl (2R)-2-[3-(2-hydroxy-5-oxopyrrolidin-1-yl)prop-1-ynyl]piperidine-1-carboxylate
  参考文献：
  名称：

  Synthesis and in vitro characterization of novel amino terminally modified oxotremorine derivatives for brain muscarinic receptors

  摘要：

  A series of novel 2-substituted acetylenic pyrrolidines and piperidines related to oxotremorine (1) were prepared and evaluated in vitro as muscarinic cholinergic agents at brain M1 and M2 receptors. One analogue, 3-(2-oxo-1-pyrrolidinyl)-1-[2 (R)-pyrrolidinyl]-1-propyne hydrogen oxalate (6a), was found to be a partial agonist producing a PI hydrolysis response at cortical M1 receptors approximately 3-fold larger than that produced by 1. The intrinsic activity profile of 6a at brain muscarinic receptors is similar to those of azetidine oxo analogue 2 and dimethylamino oxo analogue (3). All three compounds are partial M1 agonists and full M2 agonists; however, the profile of 6a in binding studies is significantly different. While 2 and 3 exhibit large M2 selectivities ranging between 8-fold to several hundred-fold, the binding profile of 6a shows almost no subtype selectivity.

  DOI：

  10.1021/jm00087a008

文献信息

• Synthesis of chiral α-acetylenic cyclic amines from α-amino acids: Applications to differentially constrained oxotremorine analogues as muscarinic agents
  作者：John Y.L. Chung、James T. Wasicak

  DOI：10.1016/s0040-4039(00)94471-x

  日期：1990.1
• [EN] ALKYNYL AMINES THAT REGULATE CHOLINERGIC NEUROTRANSMISSION
  申请人：ABBOTT LABORATORIES

  公开号：WO1991000724A1

  公开（公告）日：1991-01-24

  (EN) A compound that regulates cortical cholinergic neurotransmission of formula (I), wherein A is (1) a functionalized lactam; (2) a a functionalized azacycloalkyl group; (3) a functionalized carbonylaminomethyl group; or (4) a functionalized oxyalkyl group; and B is (1) a functionalized pyrrolidin-2-yl group; (2) a functionalized aminomethyl group; (3) a 5-membered heterocycle containing two heteroatoms; or (4) a piperidine derivative; or a pharmaceutically acceptable salt thereof.(FR) L'invention concerne un composé de régulation de la neurotransmission cholinergique corticale ayant la formule (I), dans laquelle A représente (1) une lactame fonctionnalisée; (2) un groupe azacycloalkyle fonctionnalisé; (3) un groupe carbonylaminométhyle fonctionnalisé; ou (4) un groupe oxyalkyle fonctionnalisé; et B représente (1) un groupe pyrrolidine-2-yl fonctionnalisé; (2) un groupe aminométhyle fonctionnalisé; (3) un hétérocycle à 5 membres contenant deux hétéro-atomes; ou (4) un dérivé de pipéridine, ou son sel pharmaceutiquement acceptable.
• Synthesis and in vitro characterization of novel amino terminally modified oxotremorine derivatives for brain muscarinic receptors
  作者：David S. Garvey、James T. Wasicak、John Y. L. Chung、Youe Kong Shue、George M. Carrera、Paul D. May、Michael M. McKinney、David Anderson、Evelyn Cadman

  DOI：10.1021/jm00087a008

  日期：1992.5

  A series of novel 2-substituted acetylenic pyrrolidines and piperidines related to oxotremorine (1) were prepared and evaluated in vitro as muscarinic cholinergic agents at brain M1 and M2 receptors. One analogue, 3-(2-oxo-1-pyrrolidinyl)-1-[2 (R)-pyrrolidinyl]-1-propyne hydrogen oxalate (6a), was found to be a partial agonist producing a PI hydrolysis response at cortical M1 receptors approximately 3-fold larger than that produced by 1. The intrinsic activity profile of 6a at brain muscarinic receptors is similar to those of azetidine oxo analogue 2 and dimethylamino oxo analogue (3). All three compounds are partial M1 agonists and full M2 agonists; however, the profile of 6a in binding studies is significantly different. While 2 and 3 exhibit large M2 selectivities ranging between 8-fold to several hundred-fold, the binding profile of 6a shows almost no subtype selectivity.