(-)-(R)-3-(4-chlorophenoxy)-2-methyl-1-propanol | 148144-59-6

• 英文名称: (-)-(R)-3-(4-chlorophenoxy)-2-methyl-1-propanol
• 英文别名: R-(-)-2-methyl-3-(4-chloro-phenoxy)-1-propanol；(2R)-3-(4-chlorophenoxy)-2-methylpropan-1-ol
• CAS: 148144-59-6
• 化学式: C₁₀H₁₃ClO₂
• 分子量: 200.665
• InChiKey: RGOCHDYZWGFRBO-MRVPVSSYSA-N

物化性质

• 沸点：
  295.5±15.0 °C(Predicted)
• 密度：
  1.161±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (-)-(R)-3-(4-chlorophenoxy)-2-methyl-1-propanol 在 sodium hydroxide 、 三乙胺 作用下， 以 二氯甲烷 、 异丙醇 为溶剂， 反应 8.17h， 生成 (+)-(R)-4-methyl-1-[3-(4-chlorophenoxy)-2-methyl-propyl]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：

  (R)-(-)-3-溴-2-甲基-1-丙醇 、 对氯苯酚 在 sodium hydroxide 作用下， 反应 0.75h， 以31%的产率得到(-)-(R)-3-(4-chlorophenoxy)-2-methyl-1-propanol
  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

文献信息

• Loiodice; Ferorelli; Tangari, Il Farmaco, 1993, vol. 48, # 1, p. 45 - 63
  作者：Loiodice、Ferorelli、Tangari、Bettoni、Tortorella、Pierno、De Luca、Tricarico、Conte-Camerino

  DOI：——

  日期：——