methoxy(2-naphthyl)acetic acid | 7362-01-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: methoxy(2-naphthyl)acetic acid
• 英文别名: α-Methoxy-naphthyl-(2)-essigsaeure；Methoxy-2-naphthylacetic acid；2-methoxy-2-naphthalen-2-ylacetic acid
• CAS: 7362-01-8
• 化学式: C₁₃H₁₂O₃
• 分子量: 216.236
• InChiKey: OQVFHDWREDKUCW-UHFFFAOYSA-N

物化性质

• 熔点：
  83.5 °C
• 沸点：
  396.2±22.0 °C(Predicted)
• 密度：
  1.238±0.06 g/cm3(Predicted)

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：

  methoxy(2-naphthyl)acetic acid 在 氯化亚砜 作用下， 以 苯 为溶剂， 反应 6.0h， 生成 2-methoxy-2-naphthalen-2-ylacetyl chloride
  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：

  (+/-)-Methyl α-methoxy-α-(2-naphthyl)acetate 在 alkali 作用下， 以62%的产率得到methoxy(2-naphthyl)acetic acid
  参考文献：
  名称：

  Conformational Structure and Dynamics of Arylmethoxyacetates: DNMR Spectroscopy and Aromatic Shielding Effect

  摘要：

  The ground state conformational geometry and energy of esters of (R)- and (S)-arylmethoxyacetic acids were evaluated from low temperature H-1 and C-13 NMR spectra and by means of MM, AM1, and aromatic shielding effect calculations. In solution, the title compounds are constituted by two rotamers in equilibrium. Rotamer ap has the C-alpha-O and C=O bonds antiperiplanar and rotamer sp (lower in energy by 0.4-1.1 kcal/mol) has these bonds synperiplanar. In both the ap and the sp the aryl ring is ca. perpendicular to the C=O bond and coplanar with the CalphaH bond. Their relative populations and its temperature dependence evaluated by DNMR spectra are in agreement with the stereoselectivity reported for Diels-Alder reactions of dienyl-AMAA esters and support the ''perpendicular model'' proposed to account for that stereoselectivity. For conformations in which the aryl ring shields the alcohol moiety of the ester, calculated ring current shielding increments compare well with experimental shift values obtained from low-temperature NMR spectra and agree with the conformational model used in the Mislow-Dale-Mosher-Trost method for chiral recognition by NMR.

  DOI：

  10.1021/jo00108a008

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。
• Chemo-enzymatic synthesis of enantiomerically pure (R)-2-naphthylmethoxyacetic acid
  作者：Mayumi Kimura、Atsuhito Kuboki、Takeshi Sugai

  DOI：10.1016/s0957-4166(02)00242-2

  日期：2002.6

  Enantiomerically pure (R)-2-naphthylmethoxyacetic acid (2-NMA) was synthesized from 2-naphthaldehyde via an integrated chemo-enzymatic procedure. The one-pot, successive use of SnBr2–TMSCN and AcBr worked effectively to give a racemic cyanohydrin acetate. Lipase from Burkholderia cepacia then mediated the highly enantioselective hydrolysis of the (S)-enantiomer of the racemate, leaving the (R)-acetate

  对映体纯的（R）-2-萘甲氧基乙酸（2-NMA）是由2-萘醛通过整合的化学酶促程序合成的。单锅连续使用SnBr 2 -TMSCN和AcBr可以有效地产生外消旋氰醇乙酸酯。然后来自洋葱伯克霍尔德氏菌的脂肪酶介导外消旋物的（S）-对映体的高度对映选择性水解，使（R）-乙酸酯的ee大于99.9％。将得到的这种酶催化水解，一个的产物（小号）-氰醇自发地分解为萘甲醛（该合成途径的起始原料），可以回收利用。在非常温和的条件下，用微生物Rhodococcus rhodochrous将腈水合成酰胺，以及将乙酸酯水解，而不会损失任何对映体纯度。用亚硝酰基硫酸水解酰胺基，并分离出产物，为α-羟基酯。用重氮甲烷硅胶将α-羟基甲基化，最后的任务是酯水解，在中等至中等pH的条件下，用产自克雷伯氏菌的酯酶进行酯化，得到对映体纯的2-NMA。
• 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。
• Determination of Absolute Configurations of Tertiary Alcohols by NMR Spectroscopy
  作者：Haruko Takahashi、Naoko Kato、Makoto Iwashima、Kazuo Iguchi

  DOI：10.1246/cl.1999.1181

  日期：1999.11

  A method has been developed for determining the absolute configurations of acyclic tertiary alcohols using their 2NMA [methoxy-(2-naphthyl)acetic acid] esters. The 1H NMR spectra of (R)- and (S)-2NMA esters of model compounds were measured, and Δδ values (δR-ester − δS-ester) were calculated. The absolute configuration for tertiary hydroxy group is determined based on the sign of Δδ values like that

  已开发出一种使用其 2NMA [甲氧基-(2-萘基) 乙酸] 酯测定无环叔醇绝对构型的方法。测量模型化合物的(R)-和(S)-2NMA酯的1H NMR谱，并计算Δδ值(δR-酯-δS-酯)。叔羟基的绝对构型是根据 Δδ 值的符号确定的，就像仲羟基的符号一样。