O-methanesulfonyl-3-(4-chlorophenoxy)-1-propanol | 63650-14-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: O-methanesulfonyl-3-(4-chlorophenoxy)-1-propanol
• 英文别名: 3-(4-chlorophenoxy)-1-propanol O-methanesulfonate；3-(4-chlorophenoxy)propyl methanesulfonate
• CAS: 63650-14-6
• 化学式: C₁₀H₁₃ClO₄S
• 分子量: 264.73
• InChiKey: IRTQUWPZPJDVPX-UHFFFAOYSA-N

物化性质

• 沸点：
  437.5±25.0 °C(Predicted)
• 密度：
  1.308±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  61
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-甲基哌啶 、 O-methanesulfonyl-3-(4-chlorophenoxy)-1-propanol 在 sodium hydroxide 作用下， 以 异丙醇 、 水 为溶剂， 反应 5.17h， 生成 4-methyl-1-[3-(4-chlorophenoxy)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：

  对氯苯酚 在 sodium hydroxide 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 3.75h， 生成 O-methanesulfonyl-3-(4-chlorophenoxy)-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

• Method of treating lipidemia with aryloxyalkylaminobenzoic acids and
  申请人：American Cyanamid Company

  公开号：US04182776A1

  公开（公告）日：1980-01-08

  Aryloxyalkylaminobenzoic acids and esters as hypolipemic compounds.

  芳氧烷基氨基苯甲酸和酯作为降脂化合物。
• US4681879A
  申请人：——

  公开号：US4681879A

  公开（公告）日：1987-07-21
• Synthesis of Chiral 1-[ω-(4-Chlorophenoxy)alkyl]-4-methylpiperidines and Their Biological Evaluation at σ₁, σ₂, and Sterol Δ₈−Δ₇ Isomerase Sites
  作者：Francesco Berardi、Fulvio Loiodice、Giuseppe Fracchiolla、Nicola Antonio Colabufo、Roberto Perrone、Vincenzo Tortorella

  DOI：10.1021/jm021014d

  日期：2003.5.1

  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.