(R)-1-(4-chlorophenoxy)-2-(4-methyl-2,6-piperidindion-1-yl)propane | 545376-19-0

• 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: (R)-1-(4-chlorophenoxy)-2-(4-methyl-2,6-piperidindion-1-yl)propane
• 英文别名: 1-[(2R)-1-(4-chlorophenoxy)propan-2-yl]-4-methylpiperidine-2,6-dione
• CAS: 545376-19-0
• 化学式: C₁₅H₁₈ClNO₃
• 分子量: 295.766
• InChiKey: OXEUGFFRIYUSJX-LLVKDONJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R)-1-(4-chlorophenoxy)-2-(4-methyl-2,6-piperidindion-1-yl)propane 在 dimethyl sulfide borane 、 盐酸 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 6.0h， 生成 (+)-(R)-4-methyl-1-[2-(4-chlorophenoxy)-1-methyl-ethyl]piperidine
  参考文献：
  名称：

  Synthesis of Chiral 1-[ω-(4-Chlorophenoxy)alkyl]-4-methylpiperidines and Their Biological Evaluation at σ₁, σ₂, and Sterol Δ₈−Δ₇ Isomerase Sites

  摘要：

  Sumitomo's patented sigma ligand 1-[3-(4-chlorophenoxy)propyll-4-methylpiperidine (15), which has been claimed as agent for CNS disorders and neuropathies, and its lower homologue 12 were prepared along with related chiral (4-chlorophenoxy)alkylpiperidines. They were tested at sigma(1), sigma(2), and sterol Delta(8)-Delta(7) isomerase (SI) sites by in vitro radioligand binding assays, to evaluate the influence of a chiral center in the alkyl chain on the selective a, binding relative to other a family sites. Generally high alpha(1)-site affinities were found, so that the chirality introduced by a methyl substitution resulted in slight differences. Nevertheless, the shorter oxyethylenic chain was beneficial to increase a, selectivity. However, the (-)-(S)-4-methyl-1-[2-(4-chlorophenoxy)1-methylethyl]piperidine ((-)-(S)-17) reached the highest sigma(1) affinity (K-i = 0.34 nM) and the best selectivity relative to the sigma(2) site (547-fold). Compound (-)-(S)-17 displayed also a moderate selectivity (11-fold) relative to the SI site.

  DOI：

  10.1021/jm021014d
• 作为产物：
  描述：

  3-甲基戊二酸 在 乙酰氯 作用下， 以 四氢呋喃 为溶剂， 反应 8.0h， 生成 (R)-1-(4-chlorophenoxy)-2-(4-methyl-2,6-piperidindion-1-yl)propane
  参考文献：
  名称：

  Synthesis of Chiral 1-[ω-(4-Chlorophenoxy)alkyl]-4-methylpiperidines and Their Biological Evaluation at σ₁, σ₂, and Sterol Δ₈−Δ₇ Isomerase Sites

  摘要：

  Sumitomo's patented sigma ligand 1-[3-(4-chlorophenoxy)propyll-4-methylpiperidine (15), which has been claimed as agent for CNS disorders and neuropathies, and its lower homologue 12 were prepared along with related chiral (4-chlorophenoxy)alkylpiperidines. They were tested at sigma(1), sigma(2), and sterol Delta(8)-Delta(7) isomerase (SI) sites by in vitro radioligand binding assays, to evaluate the influence of a chiral center in the alkyl chain on the selective a, binding relative to other a family sites. Generally high alpha(1)-site affinities were found, so that the chirality introduced by a methyl substitution resulted in slight differences. Nevertheless, the shorter oxyethylenic chain was beneficial to increase a, selectivity. However, the (-)-(S)-4-methyl-1-[2-(4-chlorophenoxy)1-methylethyl]piperidine ((-)-(S)-17) reached the highest sigma(1) affinity (K-i = 0.34 nM) and the best selectivity relative to the sigma(2) site (547-fold). Compound (-)-(S)-17 displayed also a moderate selectivity (11-fold) relative to the SI site.

  DOI：

  10.1021/jm021014d