oxime of 6-methoxy-2-naphthyl aldehyde

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: oxime of 6-methoxy-2-naphthyl aldehyde
• 英文别名: 6-methoxy-2-naphthaldoxime；N-[(6-methoxynaphthalen-2-yl)methylidene]hydroxylamine
• 化学式: C₁₂H₁₁NO₂
• mdl: MFCD00449337
• 分子量: 201.225
• InChiKey: AGQKMDQKTWXGMX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.083
• 拓扑面积：
  41.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  oxime of 6-methoxy-2-naphthyl aldehyde 在 (Bu₄N)₂S₂O₈ 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 1.5h， 以87.5%的产率得到6-甲氧基-2-萘甲醛
  参考文献：
  名称：

  有机合成中的四丁基过硫酸铵；IV.1四丁基过硫酸铵的高效、高选择性和氧化脱肟

  摘要：

  摘要 四丁基过二硫酸铵已被证明是一种高效且具有高度化学选择性的试剂，可在温和条件下将肟转化为相应的羰基化合物。

  DOI：

  10.1080/00397919908086071
• 作为产物：
  描述：

  6-甲氧基-2-萘甲醛 在 盐酸羟胺 、 sodium acetate 作用下， 以 乙醇 为溶剂， 反应 6.0h， 生成 oxime of 6-methoxy-2-naphthyl aldehyde
  参考文献：
  名称：

  亚硝酸钠催化的好氧氧化Csp2 ？Csp3偶联：4芳基二氢异喹啉酮部分的直接构建

  摘要：

  为4 aryldihydroisoquinolinone部分的结构的仿生方法通过直接氧化Ç SP 2  ç SP 3耦合已被开发出来，它使用便宜的亚硝酸钠作为催化剂和对环境无害的空气中的氧气作为氧化剂终端。

  DOI：

  10.1002/adsc.201300832

文献信息

• Sodium Nitrite-Catalyzed Aerobic Oxidative C<i>sp</i>²C<i>sp</i>³Coupling: Direct Construction of the 4-Aryldihydroisoquinolinone Moiety
  作者：Bo Su、Meng Deng、Qingmin Wang

  DOI：10.1002/adsc.201300832

  日期：2014.3.24

  A bioinspired approach for the construction of the 4‐aryldihydroisoquinolinone moiety via direct oxidative Csp2Csp3 coupling has been developed, which uses inexpensive sodium nitrite as catalyst and environmentally benign oxygen in the air as terminal oxidant.

  为4 aryldihydroisoquinolinone部分的结构的仿生方法通过直接氧化Ç SP 2  ç SP 3耦合已被开发出来，它使用便宜的亚硝酸钠作为催化剂和对环境无害的空气中的氧气作为氧化剂终端。
• Tetrabutylammonium Peroxydisulfate in Organic Synthesis; IV.¹An Efficient, Highly Selective and Oxidative Deoximation by Tetrabutylammonium Peroxydisulfate
  作者：Fener Chen、Anchang Liu、Qiongjiao Yan、Mingxing Liu、Daoming Zhang、Lanying Shao

  DOI：10.1080/00397919908086071

  日期：1999.3

  Abstract Tetrabutylammonium peroxydisulfate has been proved out to be an efficient and highly chemoselective reagent for the conversion of oximes to the corresponding carbonyl compounds under mild conditions.

  摘要 四丁基过二硫酸铵已被证明是一种高效且具有高度化学选择性的试剂，可在温和条件下将肟转化为相应的羰基化合物。
• Glucose-derived spiro-isoxazolines are anti-hyperglycemic agents against type 2 diabetes through glycogen phosphorylase inhibition
  作者：David Goyard、Bálint Kónya、Aikaterini S. Chajistamatiou、Evangelia D. Chrysina、Jérémy Leroy、Sophie Balzarin、Michel Tournier、Didier Tousch、Pierre Petit、Cédric Duret、Patrick Maurel、László Somsák、Tibor Docsa、Pál Gergely、Jean-Pierre Praly、Jacqueline Azay-Milhau、Sébastien Vidal

  DOI：10.1016/j.ejmech.2015.12.004

  日期：2016.1

  Glycogen phosphorylase (GP) is a target for the treatment of hyperglycaemia in the context of type 2 diabetes. This enzyme is responsible for the depolymerization of glycogen into glucose thereby affecting the levels of glucose in the blood stream. Twelve new D-glucopyranosylidene-spiro-isoxazolines have been prepared from O-peracylated exo-D-glucals by regio- and stereoselective 1,3-dipolar cycloaddition of nitrile oxides generated in situ by treatment of the corresponding oximes with bleach. This mild and direct procedure appeared to be applicable to a broad range of substrates. The corresponding 0-unprotected spiro-isoxazolines were evaluated as glycogen phosphorylase (GP) inhibitors and exhibited IC50 values ranging from 1 to 800 mu M. Selected inhibitors were further evaluated in vitro using rat and human hepatocytes and exhibited significant inhibitory properties in the primary cell culture. Interestingly, when tested with human hepatocytes, the tetra-O-acetylated spiro-isoxazoline bearing a 2-naphthyl residue showed a much lower IC50 value (2.5 mu M), compared to that of the 0-unprotected analog (19.95 mu M). The most promising compounds were investigated in Zucker fa/fa rat model in acute and sub-chronic assays and decreased hepatic glucose production, which is known to be elevated in type 2 diabetes. This indicates that glucose-based spiro-isoxazolines can be considered as anti-hyperglycemic agents in the context of type 2 diabetes. (C) 2015 Elsevier Masson SAS. All rights reserved.