(+/-)-Methyl α-methoxy-α-(1-naphthyl)acetate | 13158-05-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (+/-)-Methyl α-methoxy-α-(1-naphthyl)acetate
• 英文别名: methyl α-methoxy-1-naphthaleneacetate；-methoxy-essigsaeuremethylester；Methoxy--essigsaeuremethylester；Methyl-α-methoxy-1-naphthylacetat；Methyl 2-methoxy-2-naphthalen-1-ylacetate
• CAS: 13158-05-9
• 化学式: C₁₄H₁₄O₃
• 分子量: 230.263
• InChiKey: OABQJBJSJGQKPZ-UHFFFAOYSA-N

物化性质

• 沸点：
  151 °C(Press: 0.2 Torr)
• 密度：
  1.151±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (+/-)-Methyl α-methoxy-α-(1-naphthyl)acetate 在 氯化亚砜 、 lithium hydroxide monohydrate 作用下， 以 甲醇 、 水 、 苯 为溶剂， 反应 30.0h， 生成
  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 、 silver(l) oxide 作用下， 反应 40.5h， 生成 (+/-)-Methyl α-methoxy-α-(1-naphthyl)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

文献信息

• Electrochemical Methoxylation of Arylacetates.
  作者：Mitsuko KATO、Shohei SUZUKI、Miyako SHIMAMURA、Koohei NOZAWA、Ken-ichi KAWAI、Shoichi NAKAJIMA

  DOI：10.1248/cpb.40.1037

  日期：——

  Electrochemical methoxylation at the active methylene group of phenylacetates and 1-naphthaleneacetate was conducted successfully at room temperature, in methanol containing potassium iodide as an electron carrier and solium methoxide as a bade and a methoxylating agent. Along with the mono-methoxylated products, dimethoxy, hydroxy, and oxo derivatives as well as the dimers (succinates) were produced as by-products.

  在室温下，在苯乙酸和1-萘乙酸的活性亚甲基上成功进行了电化学甲氧基化反应，反应介质为甲醇，电子载体为碘化钾，催化剂和甲氧基化剂为甲醇钠。除单甲氧基化产物外，还产生了二甲氧基、羟基和氧基衍生物以及二聚体（琥珀酸酯）等副产物。
• Conformational Structure and Dynamics of Arylmethoxyacetates: DNMR Spectroscopy and Aromatic Shielding Effect
  作者：Sh. K. Latypov、J. M. Seco、E. Quinoa、R. Riguera

  DOI：10.1021/jo00108a008

  日期：1995.2

  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.
• Gross,H.; Freiberg,J., Chemische Berichte, 1967, vol. 100, p. 3777 - 3781
  作者：Gross,H.、Freiberg,J.

  DOI：——

  日期：——
• Grosz,H.; Freiberg,J., Chemische Berichte, 1966, vol. 99, p. 3260 - 3267
  作者：Grosz,H.、Freiberg,J.

  DOI：——

  日期：——
• Artemisinin (Qinghaosu) Derivatives, Their Preparation Methods And Their Use, And Pharmaceutical Compositions Containing The Same
  申请人：Li Ying

  公开号：US20080139642A1

  公开（公告）日：2008-06-12

  The invention provides a type of artemisinin derivatives having following structure I, its preparation method and use, as well as a pharmaceutical composition containing such artemisinin derivatives and its use. The artemisinin derivatives of the present invention and their pharmaceutical composition containing the artemisinin derivatives. have immunosuppressive activities and can be used more safely. The composition which comprises the artemisinin derivatives can be formulated into long-term dosage forms such as tablet, pellet and the like, and have wider productive and use value.