meso-N-methyl-2.6-diphenylpiperidine | 86926-24-1

• 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: meso-N-methyl-2.6-diphenylpiperidine
• 英文别名: cis-2,6-diphenyl-1-methylpiperidine；(2S,6R)-1-methyl-2,6-diphenylpiperidine；(2R,6S)-1-methyl-2,6-diphenylpiperidine
• CAS: 86926-24-1
• 化学式: C₁₈H₂₁N
• 分子量: 251.371
• InChiKey: VROYEMJXXLQQDX-HDICACEKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  1-methyl-2,6-diphenylpyridin-1-ium 4-methylbenzenesulfonate 在 甲醇 、 sodium tetrahydroborate 、 palladium on activated charcoal 、 氢气 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、68.95 kPa 条件下， 生成 meso-N-methyl-2.6-diphenylpiperidine
  参考文献：
  名称：

  Synthesis and evaluation of a series of homologues of lobelane at the vesicular monoamine transporter-2

  摘要：

  A series of lobelane homologues has been synthesized and evaluated for their [(3)H]DTBZ binding affinity at the vesicular monoamine transporter-2 (VMAT2). The structure-activity relationships (SAR) indicate that for retention of binding affinity at VMAT2, the lengths of the methylene linkers should be no shorter than one methylene unit at C-6 of the piperidine ring, and no shorter than two methylene units at C-2 of the piperidine ring. These results indicate that the intramolecular distances between the piperidine ring and two phenyl rings in lobelane analogues are an important criterion for retention of high affinity at VMAT2. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.10.042

文献信息

• Synthesis and stereochemistry of cis-2,6-diphenyl-1-alkylpiperidines
  作者：H. Surya Prakash Rao、Elamvazhuthi Poonguzhali

  DOI：10.1016/j.tetlet.2015.09.085

  日期：2015.11

  Facile and efficient synthesis of N-alkyl-2,6-diphenylpiperidines (NADPPs) was achieved by reductive amination cyclization (RAC) reaction on 1,5-diketones using alkylammonium formate. The reaction is a useful extension of classical Leuckart reductive amination. The RAC reaction is convenient and product isolation is simple when conducted under microwave (MW) irradiation in polyethylene glycol-200 (PEG-200) medium. The N(1) alkyl groups in NADPPs prefer equatorial position in both solid and liquid states possibly due to favorable CH-pi-interactions to evade unfavorable 1,3-diaxial interactions. Incisive analysis of H-1 NMR spectra of NADPPs showed that anisotropic effects of C(2) and C(6) phenyl rings are maximum on C(3)H of the alkyl chain. (C) 2015 Elsevier Ltd. All rights reserved.
• Horner, L.; Simons, G., Phosphorus and Sulfur and the Related Elements, 1983, vol. 15, p. 165 - 176
  作者：Horner, L.、Simons, G.

  DOI：——

  日期：——
• Jeyaraman, R.; Chandrasekaran, L.; Ganapathy, K., Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical and Analytical, 1988, vol. 27, # 8, p. 695 - 697
  作者：Jeyaraman, R.、Chandrasekaran, L.、Ganapathy, K.、Gopalakrishnan, V.

  DOI：——

  日期：——
• Hydroamination of pyrylium salts
  作者：P. V. Reshetov、O. V. Fedotova、A. P. Kriven'ko、V. G. Kharchenko

  DOI：10.1007/bf00487423

  日期：1990.5
• RESHETOV, P. V.;FEDOTOVA, O. V.;KRIVENKO, A. P.;XARCHENKO, V. G., XIMIYA GETEROTSIKL. SOED.,(1990) N, S. 608-611
  作者：RESHETOV, P. V.、FEDOTOVA, O. V.、KRIVENKO, A. P.、XARCHENKO, V. G.

  DOI：——

  日期：——