1-(N,N-二苄基氨甲基)环丙醇 | 119326-94-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 1-(N,N-二苄基氨甲基)环丙醇
• 英文名称: 1-(dibenzylamino)cyclopropanol
• 英文别名: 1-(dibenzylamino)cyclopropan-1-ol
• CAS: 119326-94-2
• 化学式: C₁₇H₁₉NO
• 分子量: 253.344
• InChiKey: VSLONXXYUKRSPQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  23.5
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2922199090

反应信息

• 作为反应物：
  描述：

  1-(叔丁基二甲基硅氧基)-1-甲氧基乙烯 、 1-(N,N-二苄基氨甲基)环丙醇 在 四氯化钛 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以62%的产率得到[1-(二苄基氨基)环丙基]乙酸甲酯
  参考文献：
  名称：

  β-Amino acid substitutions and structure-based CoMFA modeling of hepatitis C virus NS3 protease inhibitors

  摘要：

  In an effort to develop a new type of HCV NS3 peptidomimetic inhibitor, a series of tripeptide inhibitors incorporating a mix of alpha- and beta-amino acids has been synthesized. To understand the structural implications of beta-amino acid substitution, the P-1, P-2, and P-3 positions of a potent tripeptide scaffold were scanned and combined with carboxylic acid and acyl sulfonamide C-terminal groups. Inhibition was evaluated and revealed that the structural changes resulted in a loss in potency compared with the a- peptide analogues. However, several compounds exhibited mu M potency. Inhibition data were compared with modeled ligand-protein binding poses to understand how changes in ligand structure affected inhibition potency. The P-3 position seemed to be the least sensitive position for beta-amino acid substitution. Moreover, the importance of a proper oxyanion hole interaction for good potency was suggested by both inhibition data and molecular modeling. To gain further insight into the structural requirements for potent inhibitors, a three-dimensional quantitative structure-activity relationship (3D- QSAR) model has been constructed using comparative molecular field analysis (CoMFA). The most predictive CoMFA model has q(2) = 0.48 and r(pred)(2) = 0.68. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.04.005
• 作为产物：
  描述：

  1-(N,N-二苄基氨基)环丙烷羧酸 在 吡啶 、 [双(三氟乙酰氧基)碘]苯 作用下， 以 苯 为溶剂， 反应 0.75h， 以30%的产率得到1-(N,N-二苄基氨甲基)环丙醇
  参考文献：
  名称：

  Decarboxylation of 1-aminocyclopropanecarboxylic acid and its derivatives

  摘要：

  DOI：

  10.1021/jo00269a013

文献信息

• VAIDYANATHAN, GANESAN;WILSON, JOSEPH W., J. ORG. CHEM., 54,(1989) N, C. 1810-1815
  作者：VAIDYANATHAN, GANESAN、WILSON, JOSEPH W.

  DOI：——

  日期：——
• Decarboxylation of 1-aminocyclopropanecarboxylic acid and its derivatives
  作者：Ganesan Vaidyanathan、Joseph W. Wilson

  DOI：10.1021/jo00269a013

  日期：1989.4
• β-Amino acid substitutions and structure-based CoMFA modeling of hepatitis C virus NS3 protease inhibitors
  作者：Johanna Nurbo、Shane D. Peterson、Göran Dahl、U. Helena Danielson、Anders Karlén、Anja Sandström

  DOI：10.1016/j.bmc.2008.04.005

  日期：2008.5

  In an effort to develop a new type of HCV NS3 peptidomimetic inhibitor, a series of tripeptide inhibitors incorporating a mix of alpha- and beta-amino acids has been synthesized. To understand the structural implications of beta-amino acid substitution, the P-1, P-2, and P-3 positions of a potent tripeptide scaffold were scanned and combined with carboxylic acid and acyl sulfonamide C-terminal groups. Inhibition was evaluated and revealed that the structural changes resulted in a loss in potency compared with the a- peptide analogues. However, several compounds exhibited mu M potency. Inhibition data were compared with modeled ligand-protein binding poses to understand how changes in ligand structure affected inhibition potency. The P-3 position seemed to be the least sensitive position for beta-amino acid substitution. Moreover, the importance of a proper oxyanion hole interaction for good potency was suggested by both inhibition data and molecular modeling. To gain further insight into the structural requirements for potent inhibitors, a three-dimensional quantitative structure-activity relationship (3D- QSAR) model has been constructed using comparative molecular field analysis (CoMFA). The most predictive CoMFA model has q(2) = 0.48 and r(pred)(2) = 0.68. (C) 2008 Elsevier Ltd. All rights reserved.