(R)-2-amino-1-(4-chlorophenoxy)propane | 545376-15-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (R)-2-amino-1-(4-chlorophenoxy)propane
• 英文别名: (2R)-1-(4-Chlorophenoxy)-2-propanamine；(2R)-1-(4-chlorophenoxy)propan-2-amine
• CAS: 545376-15-6
• 化学式: C₉H₁₂ClNO
• 分子量: 185.653
• InChiKey: ABUVVMITUVCSDX-SSDOTTSWSA-N

物化性质

• 沸点：
  277.3±20.0 °C(Predicted)
• 密度：
  1.142±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  35.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (R)-2-amino-1-(4-chlorophenoxy)propane 在 dimethyl sulfide borane 作用下， 以 四氢呋喃 为溶剂， 反应 11.0h， 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：

  (+)-(R)-2-phthalimido-1-(4-chlorophenoxy)propane 在 一水合肼 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 反应 7.0h， 以43%的产率得到(R)-2-amino-1-(4-chlorophenoxy)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

文献信息

• A Chemoenzymatic Cascade Combining a Hydration Catalyst with an Amine Dehydrogenase: Synthesis of Chiral Amines
  作者：Fengwei Chang、Chengyi Wang、Qipeng Chen、Yongjin Zhang、Guohua Liu

  DOI：10.1002/anie.202114809

  日期：2022.3

  carbene complex was combined with a free amine dehydrogenase (GkAmDH) as a co-catalyst, enabling a cascade synthetic route to directly access chiral amines from propargylethers. This process, combining an initial gold carbene catalyzed hydration of propargylethers to ketones followed by a subsequent reductive amination, produces a wide range of chiral amines in high yields and excellent enantioselectivities

  封装的金卡宾复合物与作为助催化剂的游离胺脱氢酶 ( Gk AmDH) 结合，实现了从炔丙基醚直接获取手性胺的级联合成路线。该过程将最初的金卡宾催化的炔丙基醚水合为酮，然后进行还原胺化，以高产率和优异的对映选择性生产各种手性胺。