(R)-2-(1-naphthoxy)propanol | 92446-91-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (R)-2-(1-naphthoxy)propanol
• 英文别名: (2R)-2-naphthalen-1-yloxypropan-1-ol
• CAS: 92446-91-8
• 化学式: C₁₃H₁₄O₂
• 分子量: 202.253
• InChiKey: JBVJVSQWTXVULV-SNVBAGLBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 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)-2-(1-naphthoxy)propanol 在 正丁基锂 、 三乙胺 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 0.5h， 生成
  参考文献：
  名称：

  Synthesis, conformation analysis and catalytic properties of chiral zirconium complexes containing etherfunctionalized Cp ligands

  摘要：

  A novel series of chiral ligands was synthesized having a cyclopentadienyl (Cp) ring attached to an ether moiety. Four chiral monoCp zirconium derivatives contain these ligands in a bidentate Cp/O coordination mode. Complexes 4d, 6d, and 7d bear an aryl group at the end of the ether chain. The racemic complexes 3d and 4d show moderate activity for the polymerisation of ethylene. Complexes 6d and 7d are enantiopure and were used as asymmetric Lewis acid catalysts for the hydrocyanation of benzaldehyde. The negligible enantiomeric excess thereby is due to decomplexation of the weakly coordinated aryl ether side-chains during catalysis. (C) 1999 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0022-328x(99)00164-3
• 作为产物：
  描述：

  (R)-(-)-ethyl 2-(naphthalen-1-yloxy)propionate 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 6.0h， 以90%的产率得到(R)-2-(1-naphthoxy)propanol
  参考文献：
  名称：

  Synthesis, conformation analysis and catalytic properties of chiral zirconium complexes containing etherfunctionalized Cp ligands

  摘要：

  A novel series of chiral ligands was synthesized having a cyclopentadienyl (Cp) ring attached to an ether moiety. Four chiral monoCp zirconium derivatives contain these ligands in a bidentate Cp/O coordination mode. Complexes 4d, 6d, and 7d bear an aryl group at the end of the ether chain. The racemic complexes 3d and 4d show moderate activity for the polymerisation of ethylene. Complexes 6d and 7d are enantiopure and were used as asymmetric Lewis acid catalysts for the hydrocyanation of benzaldehyde. The negligible enantiomeric excess thereby is due to decomplexation of the weakly coordinated aryl ether side-chains during catalysis. (C) 1999 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0022-328x(99)00164-3

文献信息

• Chiral Aryloxyalkylamines: Selective 5-HT1B/1D Activation and Analgesic Activity
  作者：Alessia Carocci、Giovanni Lentini、Alessia Catalano、Maria Maddalena Cavalluzzi、Claudio Bruno、Marilena Muraglia、Nicola Antonio Colabufo、Nicoletta Galeotti、Filomena Corbo、Rosanna Matucci、Carla Ghelardini、Carlo Franchini

  DOI：10.1002/cmdc.200900530

  日期：2010.5.3

  A series of chiral 2,3‐dichlorophenoxy and 1‐naphthyloxy alkylamines were synthesized, and their binding affinities towards 5‐HT1D and h5‐HT1B receptors were evaluated. In the naphthyloxy series, the (R)‐prolinol derivative was the most selective 5‐HT1D ligand, while (S)‐N‐methyl‐2‐(1‐naphthyloxy)propan‐1‐amine showed the highest selectivity for h5‐HT1B. Both compounds performed as 5‐HT1D agonists

  合成了一系列手性2,3-二氯苯氧基和1-萘氧基烷基胺，并评估了它们对5-HT 1D和h5-HT 1B受体的结合亲和力。在萘氧基系列中，（ R ）-脯氨醇衍生物是选择性最高的5-HT 1D配体，而（ S ） -N-甲基-2-（1-萘氧基）丙-1-胺对h5-的选择性最高HT 1B。两种化合物在分离的豚鼠试验中均作为5‐HT 1D激动剂发挥作用，并且显示出比舒马曲坦和非手性类似物20  b更高的镇痛活性。在鼠标热板测试中。两种配体都没有对小鼠脑膜中存在的烟碱型ACh受体表现出任何亲和力，因此表明它们的镇痛活性不会通过与这些受体的相互作用而产生。
• Microbial reduction of naphthoxypropionic acids.
  作者：YOSHIKO TSUDA

  DOI：10.1248/cpb.35.2554

  日期：——

  Racemic 2- (1-naphthoxy) propionic acid ((±) -1) and 2- (2-naphthoxy) propionic acid ((±) -4) were subjected to microbial reduction and simultaneous resolution with Glomerella cingulata (Malus and Prunus strains), Gloeosporium olivarum (G. olivarum) and Gloeosporium laeticolor (G. laeticolor), yielding (S) - (+) -2- (1-naphthoxy) propanol ((S) -2) and (R) - (+) -2- (2-naphthoxy) - propanol ((R) -5), and leaving (R) - (-) -2- (1-naphthoxy) propionic acid ((R) -1) and (S) - (-) -2- (2- naphthoxy) propionic acid ((S) -4), respectively. The optical purity of (S) - (+) -2- (1-naphthoxy) - propanol ((S) -2) reached 92% and over 99% ee when fermented with G. olivarum and Glomerella cingulata (Malus strain), respectively.

  外消旋 2-(1-萘氧基)丙酸（(±) -1）和 2-(2-萘氧基)丙酸（(±) -4）经过微生物还原，并同时与鞘氨醇球菌（Malus 和 Prunus 菌株）、橄榄球孢子菌（G. olivarum）和月桂球孢子菌（G. laeticolor）进行解析。laeticolor），分别产生（S）-（+）-2-（1-萘氧基）丙醇（（S）-2）和（R）-（+）-2-（2-萘氧基）-丙醇（（R）-5），并留下（R）-（-）-2-（1-萘氧基）丙酸（（R）-1）和（S）-（-）-2-（2-萘氧基）丙酸（（S）-4）。当用 G. olivarum 和 Glomerella cingulata（Malus 菌株）发酵时，(S) - (+) -2- (1-naphthoxy) - 丙醇（(S) -2）的光学纯度分别达到 92% 和超过 99% ee。
• TSUDA, YOSHIKO, CHEM. AND PHARM. BULL., 35,(1987) N 6, 2554-2557
  作者：TSUDA, YOSHIKO

  DOI：——

  日期：——