tert-butyl 4-[(E/Z)-2-methoxyethenyl]-4phenylpiperidine-1-carboxylate | 716358-34-8

• 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 4-[(E/Z)-2-methoxyethenyl]-4phenylpiperidine-1-carboxylate
• 英文别名: Tert-butyl 4-(2-methoxyethenyl)-4-phenylpiperidine-1-carboxylate
• CAS: 716358-34-8
• 化学式: C₁₉H₂₇NO₃
• 分子量: 317.428
• InChiKey: DJWJBURYVGMJED-UHFFFAOYSA-N

物化性质

• 沸点：
  411.3±45.0 °C(predicted)
• 密度：
  1.096±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  tert-butyl 4-[(E/Z)-2-methoxyethenyl]-4phenylpiperidine-1-carboxylate 在 对甲苯磺酸 作用下， 以 水 、 丙酮 为溶剂， 反应 48.0h， 以50%的产率得到N-Boc-4-(2-oxoethyl)-4-phenyl-1-piperidine
  参考文献：
  名称：

  Discovery of Bioavailable 4,4-Disubstituted Piperidines as Potent Ligands of the Chemokine Receptor 5 and Inhibitors of the Human Immunodeficiency Virus-1

  摘要：

  We describe robust chemical approaches toward putative CCR5 scaffolds designed in our laboratories. Evaluation of analogues in the (125)I-[MIP-1 beta] binding and Ba-L-HOS antiviral assays resulted in the discovery of 64 and 68 in the 4,4-disubstitited piperidine class H, both potent CCR5 ligands (pIC(50) = 8.30 and 9.00, respectively) and HIV-1 inhibitors (pIC(50) = 7.80 and 7.84, respectively, in Ba-L-HOS assay). In addition, 64 and 68 were bioavailable in rodents, establishing them as lead molecules for further optimization toward CCR5 clinical candidates.

  DOI：

  10.1021/jm800598a
• 作为产物：
  描述：

  1-Boc-4-phenyl-4-piperidinecarbaldehyde 在 potassium tert-butylate 、 甲氧基甲基三苯基氯化膦 作用下， 以 四氢呋喃 为溶剂， 反应 18.5h， 以68%的产率得到tert-butyl 4-[(E/Z)-2-methoxyethenyl]-4phenylpiperidine-1-carboxylate
  参考文献：
  名称：

  [EN] PIPERIDINE DERIVATIVES AS CCR5 ANTAGONISTS
  [FR] ANTAGONISTES DE CCR5 UTILES COMME AGENTS THERAPEUTIQUES

  摘要：

  公开号：

  WO2004054974A3

文献信息

• [2-(4-Phenyl-4-piperidinyl)ethyl]amine based CCR5 antagonists: derivatizations at the N-terminal of the piperidine ring
  作者：Maosheng Duan、Christopher Aquino、Robert Ferris、Wieslaw M. Kazmierski、Terry Kenakin、Cecilia Koble、Pat Wheelan、Chris Watson、Michael Youngman

  DOI：10.1016/j.bmcl.2009.02.014

  日期：2009.3

  Several series of CCR5 antagonists have been discovered by derivatization at the N-terminal of the piperidine ring of the core template 2. Some derivatives exhibited potent inhibition against HIV-1 infection. The pharmacokinetic properties of the lead compounds 11a, 14a, 15b, and 16b have been evaluated in vivo. (C) 2009 Elsevier Ltd. All rights reserved.