(3R,4R)-rel-3-羟基-1-(苯甲基)-4-哌啶腈 | 1013333-20-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 中文名称: (3R,4R)-rel-3-羟基-1-(苯甲基)-4-哌啶腈
• 英文名称: trans-1-(phenylmethyl)-4-cyano-piperidin-3-ol
• 英文别名: trans-1-benzyl-3-hydroxypiperidine-4-carbonitrile；(3R,4R)-rel-1-Benzyl-3-hydroxypiperidine-4-carbonitrile；(3R,4R)-1-benzyl-3-hydroxypiperidine-4-carbonitrile
• CAS: 1013333-20-4
• 化学式: C₁₃H₁₆N₂O
• 分子量: 216.283
• InChiKey: XZYDMOVDIBVPOL-OLZOCXBDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  47.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3R,4R)-rel-3-羟基-1-(苯甲基)-4-哌啶腈 在 镍 氨 、 氢气 作用下， 以 甲醇 为溶剂， 以81%的产率得到trans-1-(phenylmethyl)-4-(aminomethyl)-piperidin-3-ol
  参考文献：
  名称：

  Development of two diastereoselective routes towards trans-4-aminomethyl-piperidin-3-ol building blocks

  摘要：

  Two diastereoselective, scaleable routes towards trans-3,4-disubstituted piperidines with a 4-hydroxymethyl-3-hydroxy or 4-aminomethyl-3hydroxy substitution pattern are being described. In the first route, the 3,4-trans configuration was introduced regio- and diastereoselectively via a hydroboration/oxidation sequence starting from 4-hydroxymethylpyridine. In the second route, regioselective epoxide ring opening of N-benzyl-3,4-epoxy-piperidine was achieved with LiCN, in situ generated from acetocyanohydrin and LiNH(2), The regioselectivity of both the hydroboration and the epoxide ring opening was positively influenced by the presence of the basic piperidine nitrogen. Both routes have been optimized to be performed at large scale. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.12.055
• 作为产物：
  描述：

  丙酮氰醇 、 3-苄基-7-噁-3-氮杂双环4.1.0庚烷 在 lithium amide 作用下， 以 四氢呋喃 为溶剂， 反应 4.5h， 生成 (3R,4R)-rel-3-羟基-1-(苯甲基)-4-哌啶腈
  参考文献：
  名称：

  Development of two diastereoselective routes towards trans-4-aminomethyl-piperidin-3-ol building blocks

  摘要：

  Two diastereoselective, scaleable routes towards trans-3,4-disubstituted piperidines with a 4-hydroxymethyl-3-hydroxy or 4-aminomethyl-3hydroxy substitution pattern are being described. In the first route, the 3,4-trans configuration was introduced regio- and diastereoselectively via a hydroboration/oxidation sequence starting from 4-hydroxymethylpyridine. In the second route, regioselective epoxide ring opening of N-benzyl-3,4-epoxy-piperidine was achieved with LiCN, in situ generated from acetocyanohydrin and LiNH(2), The regioselectivity of both the hydroboration and the epoxide ring opening was positively influenced by the presence of the basic piperidine nitrogen. Both routes have been optimized to be performed at large scale. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.12.055

文献信息

• [EN] ISOXAZOLE CARBOXAMIDE COMPOUNDS AND USES THEREOF<br/>[FR] COMPOSÉS D'ISOXAZOLE CARBOXAMIDE ET LEURS UTILISATIONS
  申请人：NOVARTIS AG

  公开号：WO2020058913A1

  公开（公告）日：2020-03-26

  A compound of Formula (I) or or a pharmaceutically acceptable salt thereof, is provided that has been shown to be useful for treating hearing loss or balance disorder: Formula (I) wherein R1 and Y are as defined herein.

  提供了一个化合物的化学式（I）或其药用盐，已被证明对治疗听力损失或平衡障碍有用：化学式（I），其中R1和Y的定义如下。
• ISOXAZOLE CARBOXAMIDE COMPOUNDS AND USES THEREOF
  申请人：Novartis AG

  公开号：US20210355115A1

  公开（公告）日：2021-11-18

  A compound of Formula (I) or or a pharmaceutically acceptable salt thereof, is provided that has been shown to be useful for treating hearing loss or balance disorder: Formula (I) wherein R 1 and Y are as defined herein.