2-甲氧基-2-萘-1-基乙酸 | 19126-12-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 2-甲氧基-2-萘-1-基乙酸
• 英文名称: methoxy(naphthalen-1-yl)acetic acid
• 英文别名: methoxy-[1]naphthyl-acetic acid；(+/-)-Methoxy-(naphthyl-(1))-essigsaeure-aethylester；Methoxy-[1]naphthyl-essigsaeure；2-Methoxy-2-naphthalen-1-ylacetic acid
• CAS: 19126-12-6
• 化学式: C₁₃H₁₂O₃
• 分子量: 216.236
• InChiKey: MIQWXVUTCSGZIZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-甲氧基-2-萘-1-基乙酸 在 4-二甲氨基吡啶 、 氯化亚砜 、 三乙胺 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 18.5h， 生成 1-(1,3-dimethyl-2,6-dioxo-2,3-dihydro-1H-purin-7(6H)-yl)propan-2-yl 2-methoxy-2-(naphthalen-1-yl)acetate
  参考文献：
  名称：

  Synthesis of novel proxyphylline derivatives with dual Anti-Candida albicans and anticancer activity

  摘要：

  Three out of 16 newly synthesized 1,3-dimethylxanthine derivatives (proxyphylline analogues) exhibited consistencies between antifungal and anticancer properties. Proxyphylline possessing 1-(10H-phenothiazin-10-yl)propan-2-yl (6) and polybrominated benzimidazole (41) or benzotriazole moiety (42) remained selectively cidal against Candida albicans (lg R >= 3 at conc. of 31, 36 and 20 mu M, respectively) however not against normal mammalian Vero cell line in vitro (IC50 >= 280 mu M) and Galleria mellonella in vivo. These compounds also displayed moderate antineoplastic activity against human breast adenocarcinoma (MCF-7) cell line (EC50 = 80 mu M) and high against peripheral blood T lymphoblast (CCRF-CEM) (EC50 = 6.3-6.5 mu M). In addition, 6 and 42 exerted: (1) dual activity against fungal adhesion and damage mature biofilm; (2) necrosis of planktonic cells due to loss of membrane function and of structural integrity; (3) biochemical (inhibition of sessile cell respiration) and morphological changes in cell wall polysaccharide contents. Therefore, leading proxyphylline derivatives can be employed to prevent cancer-associated biofilm Candida infections. (C) 2018 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2018.02.077
• 作为产物：
  描述：

  1-萘乙醇酸 在 calcium sulfate 、 氯化亚砜 、 lithium hydroxide monohydrate 、 silver(l) oxide 作用下， 以 甲醇 、 水 为溶剂， 反应 64.5h， 生成 2-甲氧基-2-萘-1-基乙酸
  参考文献：
  名称：

  Synthesis of novel proxyphylline derivatives with dual Anti-Candida albicans and anticancer activity

  摘要：

  Three out of 16 newly synthesized 1,3-dimethylxanthine derivatives (proxyphylline analogues) exhibited consistencies between antifungal and anticancer properties. Proxyphylline possessing 1-(10H-phenothiazin-10-yl)propan-2-yl (6) and polybrominated benzimidazole (41) or benzotriazole moiety (42) remained selectively cidal against Candida albicans (lg R >= 3 at conc. of 31, 36 and 20 mu M, respectively) however not against normal mammalian Vero cell line in vitro (IC50 >= 280 mu M) and Galleria mellonella in vivo. These compounds also displayed moderate antineoplastic activity against human breast adenocarcinoma (MCF-7) cell line (EC50 = 80 mu M) and high against peripheral blood T lymphoblast (CCRF-CEM) (EC50 = 6.3-6.5 mu M). In addition, 6 and 42 exerted: (1) dual activity against fungal adhesion and damage mature biofilm; (2) necrosis of planktonic cells due to loss of membrane function and of structural integrity; (3) biochemical (inhibition of sessile cell respiration) and morphological changes in cell wall polysaccharide contents. Therefore, leading proxyphylline derivatives can be employed to prevent cancer-associated biofilm Candida infections. (C) 2018 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2018.02.077

文献信息

• [EN] PROCESSES FOR THE SYNTHESIS OF CHIRAL 1-ALKANOLS<br/>[FR] PROCÉDÉS DE SYNTHÈSE DE 1-ALCANOLS CHIRAUX
  申请人：PURDUE RESEARCH FOUNDATION

  公开号：WO2015106045A1

  公开（公告）日：2015-07-16

  The invention relates to highly enantioselective processes for the synthesis of chiral 1-alkanols via Zr-catalyzed asymmetric carboalumination of alkenes.

  这项发明涉及通过锆催化的不对称烯烃碳铝化反应合成手性1-烷醇的高对映选择性过程。
• PROCESSES FOR THE SYNTHESIS OF CHIRAL 1-ALKANOLS
  申请人：PURDUE RESEARCH FOUNDATION

  公开号：US20160332940A1

  公开（公告）日：2016-11-17

  The invention relates to highly enantioselective processes for the synthesis of chiral 1-alkanols via Zr-catalyzed asymmetric carboalumination of alkenes.

  这项发明涉及通过Zr催化的不对称烯烃碳硼烷化反应合成手性1-烷醇的高对映选择性过程。
• Chiral N-heterocyclic carbene ligands for asymmetric catalytic oxindole synthesis
  作者：Yi-Xia Jia、J. Mikael Hillgren、Emma L. Watson、Stephen P. Marsden、E. Peter Kündig

  DOI：10.1039/b810858g

  日期：——

  The Pd-catalysed asymmetric intramolecular alpha-arylation of amide enolates containing heteroatom substituents gives chiral 3-alkoxy or 3-aminooxindoles in high yield and with enantioselectivities up to 97% ee when a new chiral N-heterocyclic carbene ligand is used.

  当使用新的手性N-杂环卡宾配体时，Pd催化的含杂原子取代基的酰胺烯酸酯的不对称分子内α-芳基化反应可高收率和高达97％ee的对映选择性，产生手性3-烷氧基或3-氨基氧吲哚。
• Reaction of chloral with naphthalene, and the synthesis of α-methoxynaphthylacetic acids from naphthyl(trichloromethyl)carbinols
  作者：Wilkins Reeve、John C. Hoffsommer、Patrick F. Aluotto

  DOI：10.1139/v68-363

  日期：1968.7.1

  Friedel–Crafts reaction of chloral and naphthalene, others have reported the isolation of only 2-naphthyl(trichloromethyl)carbinol. Our reexamination of this reaction has shown that a mixture of 1- and 2-naphthyl(trichloromethyl)carbinols is obtained and that 80 to 90% of the product consists of the 1-naphthyl(trichloromethyl)carbinol. The 1- and 2-naphthyl(trichloromethyl)carbinols, their acetates

  从氯醛和萘的 Friedel-Crafts 反应中，其他人报告仅分离了 2-萘基（三氯甲基）甲醇。我们对该反应的重新检查表明，获得了 1- 和 2- 萘基（三氯甲基）甲醇的混合物，并且 80 到 90% 的产物由 1-萘基（三氯甲基）甲醇组成。1- 和 2- 萘基（三氯甲基）甲醇、它们的乙酸盐和它们的甲基醚的核磁共振 (nmr) 光谱不同，因为 1-萘基异构体侧链的 α-氢信号总是出现与相应 2-萘基异构体的 α-氢信号相比，低场 0.8 ppm。
• (R)- and (S)-α-Methoxy-(1-naphthyl) acetic acids: resolution by fractional crystallization and use for the NMR stereochemical analysis of alkylsulfoxides
  作者：Xavier Borde、Caroline Nugier-Chauvin、Nicolas Noiret、Henri Patin

  DOI：10.1016/s0957-4166(98)00077-9

  日期：1998.4

  Both enantiomers of α-methoxy-(1-naphthyl) acetic acid (1-NMA) were conveniently obtained via fractional crystallization using the enantiomers of 1-(1-naphthyl) ethylamine. 1-NMA was shown to be very powerful for differentiating the enantiomeric signals of quasi-symmetrical aliphatic sulfoxides.

  α-甲氧基-（1-萘基）乙酸（1-NMA）的两种对映体都可以通过使用1-（1-萘基）乙胺的对映体进行分步结晶而方便地获得。1-NMA被证明对区分准对称脂肪族亚砜的对映体信号非常有效。