1-(4-甲氧基-苄基)-哌啶-3-醇 | 148729-36-6

• 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: 1-(4-甲氧基-苄基)-哌啶-3-醇
• 英文名称: 1-(4-Methoxy-benzyl)-piperidin-3-ol
• 英文别名: 1-(4-Methoxybenzyl)piperidin-3-ol；1-[(4-methoxyphenyl)methyl]piperidin-3-ol
• CAS: 148729-36-6
• 化学式: C₁₃H₁₉NO₂
• mdl: MFCD01652461
• 分子量: 221.299
• InChiKey: BHSIHYZSNGOYDV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.538
• 拓扑面积：
  32.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(4-甲氧基-苄基)-哌啶-3-醇 在 三甲基氨基磺酸 、 二甲基亚砜 、 三乙胺 作用下， 生成 1-[(4-Methoxyphenyl)methyl]piperidin-3-one
  参考文献：
  名称：

  Design and synthesis of Rho kinase inhibitors (II)

  摘要：

  In a previous study, we identified several structurally unrelated scaffolds of the Rho kinase inhibitor using pharmacophore information obtained from the results of a high-throughput screening and structural information from a homology model of Rho kinase. 1H-Indazole is one of the candidate scaffolds on which a new series of potent Rho kinase inhibitors could be developed. In this study, the detailed structure-activity relationship of 1H-indazole analogues was studied. During this study, we found that the cell-free enzyme inhibitory potential of Rho kinase inhibitors having the 1H-indazole scaffold did not necessarily correlate with their inhibitory potential toward the chemotaxis of cultured cells. The choice of the linker substructure was shown to be an important factor for the 1H-indazole analogues to inhibit the chemotaxis of cells. Optimization of the 1H-indazole inhibitors with respect to the in vitro inhibition of monocyte chemotaxis induced by MCP-1 was carried out. The inhibitory potential was improved both in the cell-free enzyme assay and in the chemotaxis assay. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.09.052
• 作为产物：
  描述：

  3-羟基哌啶 、 4-甲氧基苯甲醛 在 吡啶硼烷 作用下， 以 乙醇 为溶剂， 以63%的产率得到1-(4-甲氧基-苄基)-哌啶-3-醇
  参考文献：
  名称：

  使用硼烷-吡啶用醛还原胺化哌啶

  摘要：

  摘要 硼烷-吡啶络合物 (BAP) 被发现是 Borch 还原中 NaCNBH3 的极好替代品。使用标准化条件使各种芳香族、杂环和脂肪族醛与各种取代的哌啶反应。

  DOI：

  10.1080/00397919308009840

文献信息

• Moormann Alan E., Synth. Commun., 23 (1993) N 6, S 789-795
  作者：Moormann Alan E.

  DOI：——

  日期：——
• Design and synthesis of Rho kinase inhibitors (II)
  作者：Masayuki Iwakubo、Atsuya Takami、Yuji Okada、Takehisa Kawata、Yoshimichi Tagami、Hiroshi Ohashi、Motoko Sato、Terumi Sugiyama、Kayoko Fukushima、Hiroshi Iijima

  DOI：10.1016/j.bmc.2006.09.052

  日期：2007.1.1

  In a previous study, we identified several structurally unrelated scaffolds of the Rho kinase inhibitor using pharmacophore information obtained from the results of a high-throughput screening and structural information from a homology model of Rho kinase. 1H-Indazole is one of the candidate scaffolds on which a new series of potent Rho kinase inhibitors could be developed. In this study, the detailed structure-activity relationship of 1H-indazole analogues was studied. During this study, we found that the cell-free enzyme inhibitory potential of Rho kinase inhibitors having the 1H-indazole scaffold did not necessarily correlate with their inhibitory potential toward the chemotaxis of cultured cells. The choice of the linker substructure was shown to be an important factor for the 1H-indazole analogues to inhibit the chemotaxis of cells. Optimization of the 1H-indazole inhibitors with respect to the in vitro inhibition of monocyte chemotaxis induced by MCP-1 was carried out. The inhibitory potential was improved both in the cell-free enzyme assay and in the chemotaxis assay. (c) 2006 Elsevier Ltd. All rights reserved.
• Reductive Amination of Piperidines with Aldehydes Using Borane-Pyridine
  作者：Alan E. Moormann

  DOI：10.1080/00397919308009840

  日期：1993.3

  Abstract Borane-pyridine complex (BAP) was found to be an excellent replacement for NaCNBH3 in the Borch reduction. Assorted aromatic, heterocyclic and aliphatic aldehydes were reacted with various substituted piperidines using standardized conditions.

  摘要 硼烷-吡啶络合物 (BAP) 被发现是 Borch 还原中 NaCNBH3 的极好替代品。使用标准化条件使各种芳香族、杂环和脂肪族醛与各种取代的哌啶反应。