methyl trans-1-benzyl-4-hydroxy-3-piperidinecarboxylate | 85375-47-9

• 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: methyl trans-1-benzyl-4-hydroxy-3-piperidinecarboxylate
• 英文别名: methyl rac-(3R,4R)-1-benzyl-4-hydroxypiperidine-3-carboxylate；methyl (+/-)-trans-1-benzyl-4-hydroxypiperidine-3-carboxylate；methyl (3R,4R)-1-benzyl-4-hydroxypiperidine-3-carboxylate
• CAS: 85375-47-9
• 化学式: C₁₄H₁₉NO₃
• 分子量: 249.31
• InChiKey: LNTDJAQQPGLCGB-CHWSQXEVSA-N

物化性质

• 沸点：
  376.3±42.0 °C(Predicted)
• 密度：
  1.184±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl trans-1-benzyl-4-hydroxy-3-piperidinecarboxylate 在 咪唑 、 4-二甲氨基吡啶 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 5.08h， 生成 2-[rac-(3R,4R)-1-benzyl-4-{[tert-butyl(dimethyl)silyl]oxy}piperidin-3-yl]propan-2-ol
  参考文献：
  名称：

  SUBSTITUTED (HETERO)ANILINES AND THEIR USE

  摘要：

  The present disclosure relates to substituted anilines and heteroanilines and their use as TRPV4 antagonists. In some embodiments, the disclosure provides a compound of Formula (I): (I), or a pharmaceutically acceptable salt thereof, wherein ring A, R groups, X, Y, Z, m, p, q, and s are defined herein.

  公开号：

  WO2024149728A1
• 作为产物：
  描述：

  1-苄基-3-甲氧基羰酰-4-哌啶酮 在 sodium cyanoborohydride 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 生成 methyl trans-1-benzyl-4-hydroxy-3-piperidinecarboxylate
  参考文献：
  名称：

  SUBSTITUTED (HETERO)ANILINES AND THEIR USE

  摘要：

  The present disclosure relates to substituted anilines and heteroanilines and their use as TRPV4 antagonists. In some embodiments, the disclosure provides a compound of Formula (I): (I), or a pharmaceutically acceptable salt thereof, wherein ring A, R groups, X, Y, Z, m, p, q, and s are defined herein.

  公开号：

  WO2024149728A1

文献信息

• Orally Active and Potent Inhibitors of γ-Aminobutyric Acid Uptake
  作者：Fadia E. Ali、William E. Bondinell、Penelope A. Dandridge、James S. Frazee、Eleanor Garvey、Gerald R. Girard、Carl Kaiser、Thomas W. Ku、John J. Lafferty、George I. Moonsammy、Hye-Ja Oh、Julia A. Rush、Paulette E. Setler、Orum D. Stringer、Joseph W. Venslavsky、Beth W. Volpe、Libby M. Yunger、Charles L. Zirkle

  DOI：10.1021/jm50001a020

  日期：1985.5

  3-Pyrrolidineacetic acid (1a), certain piperidinecarboxylic acids--i.e., 3-piperidinecarboxylic acid (2a), 1,2,5,6-tetrahydro-3-pyridinecarboxylic acid (3a), and cis-4-hydroxy-3-piperidinecarboxylic acid (4a)--cis-3-aminocyclohexanecarboxylic acid (5a, cis-3-ACHC), and gamma-aminobutyric acid (6a, GABA) itself are among the most potent inhibitors of [3H]GABA uptake by neurons and glia in vitro. These hydrophilic amino acids, however, do not readily enter the central nervous system in pharmacologically significant amounts following peripheral administration. We now report that N-(4,4-diphenyl-3-butenyl)-3-piperidinecarboxylic acid (2b) is a specific GABA-uptake inhibitor that is more potent, more lipophilic and, in limited testing, as selective as 2a. Similar results were obtained with the N-(4,4-diphenyl-3-butenyl) derivatives of 1a, 3a, and 4a. By contrast, N-(4,4-diphenyl-3-butenyl) derivatives of 5a and 6a were not more potent than the parent amino acids and appear to inhibit GABA uptake, at least in part, by a nonselective mechanism of action. The N-(4,4-diphenyl-3-butenyl)amino acids 1b-4b exhibit anticonvulsant activity in rodents following oral or intraperitoneal administration [Yunger, L.M.; et al. J. Pharmacol. Exp. Ther. 1984, 228, 109].
• The Absolute Configuration of the (+)- and (−)-<i>cis</i>- and (+)- and (−)-<i>trans-</i>1-Benzyl-4-hydroxypiperidine-3-methanols: An Unusual Application of the¹H-NMR-<i>Mosher</i>Method
  作者：Christian Clerc、Igor Matarazzo、Peter Rüedi

  DOI：10.1002/hlca.200800270

  日期：2009.1

  Abstractmagnified imageThe enantiomerically pure title compounds were prepared and the absolute configurations assigned by the high‐field 1H‐NMR application of the Mosher method on the bis‐MTPA derivatives (MTPA=α‐methoxy‐α‐(trifluoromethyl)benzeneacetic acid). The final evidence for the adaptability of the procedure was effected by X‐ray crystallographic analyses. The absolute configurations of the cis‐ and trans‐1‐benzyl‐4‐hydroxypiperidine‐3‐methanols are as follows: (+)‐(3S,4S) and (−)‐(3R,4R) (cis), and (+)‐(3R,4S) and (−)‐(3S,4R) (trans), respectively (Scheme 2). Nonfermenting bakers' yeast reduction of methyl 1‐benzyl‐4‐oxopiperidine‐3‐carboxylate afforded (+)‐methyl (3R,4S)‐1‐benzyl‐4‐hydroxypiperidine‐3‐carboxylate (de>97%, ee>99%) which was further reduced to the (+)‐(3S,4S)‐diol (Scheme 3). The result confirms the stereochemical outcome of the biological reduction with re‐face selectivity and cis‐diastereoselectivity as predicted for bakers' yeast. The 4‐hydroxypiperidine‐3‐methanols are the key starting compounds for the synthesis of the enantiomerically pure P(3)‐axially and P(3)‐equatorially substituted cis‐ and trans‐configurated 8‐benzyl‐2,4‐dioxa‐8‐aza‐3‐phosphadecalin 3‐oxides (=8‐benzyl‐2,4‐dioxa‐8‐aza‐3‐phospha‐bicyclo[4.4.0]decane 3‐oxides) representing γ‐homo‐acetylcholine mimetics.
• N-substituted azaheterocyclic carboxylic acids and their esters
  申请人：SMITHKLINE BECKMAN CORPORATION

  公开号：EP0066456B1

  公开（公告）日：1985-04-24
• US4383999A
  申请人：——

  公开号：US4383999A

  公开（公告）日：1983-05-17