2-(benzyloxy)-5-nitrophenol | 2242-35-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-(benzyloxy)-5-nitrophenol
• 英文别名: 5-nitro-2-phenylmethoxyphenol
• CAS: 2242-35-5
• 化学式: C₁₃H₁₁NO₄
• 分子量: 245.235
• InChiKey: ZVNBVZQNVNWAOS-UHFFFAOYSA-N

物化性质

• 熔点：
  82-85 °C
• 沸点：
  428.6±35.0 °C(Predicted)
• 密度：
  1.329±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  75.3
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(benzyloxy)-5-nitrophenol 在 platinum(IV) oxide sodium hydroxide 、 氢气 、 sodium hydride 作用下， 以 乙醇 、 乙酸乙酯 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 生成 methyl N'-[3,4-bis(phenylmethoxy)phenyl]carbamimidothioate
  参考文献：
  名称：

  New non peptidic C5a receptor antagonists

  摘要：

  A series of phenylguanidines which bind to the C5a receptor has been developed. The lead compound 1 (IC50=30 mu M), discovered through random screening, has been modified to provide 32 (RPR121154) with submicromolar activity. This compound was shown to further elicit functional antagonism in a human neutrophil C5a stimulated respiratory burst assay. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(97)00124-8
• 作为产物：
  描述：

  2-苯甲酰氧基-4-硝基-苯酚 在 氢氧化钾 、 magnesium sulfate 、 potassium carbonate 作用下， 以 乙醇 、 丙酮 为溶剂， 生成 2-(benzyloxy)-5-nitrophenol
  参考文献：
  名称：

  肾上腺能神经元阻滞剂衍生自1,4-苯并二恶烷。

  摘要：

  DOI：

  10.1021/jm00328a008

文献信息

• [EN] PYRROLOPYRIMIDINES<br/>[FR] PYRROLOPYRIMIDINES
  申请人：JANSSEN PHARMACEUTICA NV

  公开号：WO2009016132A1

  公开（公告）日：2009-02-05

  The present invention relates to compounds or pharmaceutically-acceptable salts thereof, processes for preparing them, pharmaceutical compositions containing them and their use in therapy. The invention particularly relates to compounds that are polo-like kinase (PLKs) inhibitors useful for the treatment of disease states mediated by PLK, especially PLK4, in particular such compounds that are useful in the treatment of pathological processes which involve an aberrant cellular proliferation, such as tumour growth, rheumatoid arthritis, restenosis and atherosclerosis.

  本发明涉及化合物或其药用盐，制备它们的方法，含有它们的药物组合物以及它们在治疗中的用途。该发明特别涉及一类极化样激酶（PLKs）抑制剂化合物，用于治疗由PLK介导的疾病状态，特别是PLK4，特别是在治疗涉及异常细胞增殖的病理过程中有用的化合物，如肿瘤生长、类风湿性关节炎、再狭窄和动脉粥样硬化。
• Regioselective Cleavage Reaction of the Aromatic Methylenedioxy Ring. V. Cleavage with Sodium Alkoxides - Alcohols, Potassium tert-Butoxide - Alcohols, Dimsyl Anion - Methyl Alcohol, Metallic Sodium - Alcohols, and Sodium Cyanide in Dipolar Aprotic Solvents.
  作者：Yasuhiro IMAKURA、Kazuto OKIMOTO、Tatsuya KONISHI、Mariko HISAZUMI、Junyo YAMAZAKI、Shigeru KOBAYASHI、Shinsuke YAMASHITA

  DOI：10.1248/cpb.40.1691

  日期：——

  The reaction of aromatic methylenedioxy compounds containing electron-withdrawing groups with dimsyl anion-methyl alcohol, potassium tert-butoxide-alcohols, and metallic sodium-alcohols in dimethyl sulfoxide (DMSO), and with sodium alkoxides-alcohols in hexamethylphosphoramide, gave 3- and 4-hydroxybenzene derivatives in good yield by regioselective attack of the alkoxide ions on the methylenedioxy ring. The formation mechanism of alkoxide ions and the effect of DMSO in the cleavage reaction of the methylenedioxy ring are discussed on the basis of proton nuclear magnetic resonance (1H-NMR) spectra. The reactions of aromatic methylenedioxy compounds (3 and 22) with sodium cyanide in dipolar aprotic solvents gave 4-cyano-3-hydroxybenzene derivatives (23 and 24) by regioselective attack of the cyanide ion on the methylenedioxy ring. The reactions of aromatic methylenedioxy compounds (28-30) containing no electron-withdrawing group with MeONa-MeOH in dipolar aprotic solvents gave non-regioselective cleavage products (31 and 34).

  甲基二氧芳香族化合物与二甲基亚砜（DMSO）中的二甲基磺酸酯阴离子-甲醇、叔丁醇钾-醇以及金属钠-醇反应，以及与六甲基磷酰胺中的烷氧化钠-醇反应，通过烷氧化离子对甲基二氧环的选择性攻击，以良好的产率得到3-和4-羟基苯衍生物。根据质子核磁共振（1H-NMR）谱，讨论了烷氧化离子的形成机制以及DMSO对甲基二氧环裂解反应的影响。芳香族甲基二氧化合物（3和22）与氰化钠在偶极非质子溶剂中的反应，通过氰化物离子对甲基二氧环的选择性攻击，得到4-氰基-3-羟基苯衍生物（23和24）。不含吸电子基团的芳香族甲基二氧化合物（28-30）与甲醇钠-甲醇在偶极非质子溶剂中的反应，得到非选择性裂解产物（31和34）。
• Single-Step Enantioselective Synthesis of Mechanically Planar Chiral [2]Rotaxanes Using a Chiral Leaving Group Strategy
  作者：Chong Tian、Stephen D. P. Fielden、Borja Pérez-Saavedra、Iñigo J. Vitorica-Yrezabal、David A. Leigh

  DOI：10.1021/jacs.0c03447

  日期：2020.5.27

  enantioselective synthesis of mechanically planar chiral [2]rotaxanes. Previous studies of such molecules have generally involved the separation of enantiomers from racemic mixtures or the preparation and separation of diastereomeric intermediates followed by post-assembly modification to remove other sources of chirality. Here, we demonstrate a simple asymmetric metal-free active template rotaxane synthesis using

  我们报告了机械平面手性 [2] 轮烷的一步对映选择性合成。以前对此类分子的研究通常涉及从外消旋混合物中分离对映异构体或制备和分离非对映异构中间体，然后进行组装后修饰以去除其他手性来源。在这里，我们展示了一种简单的不对称无金属活性模板轮烷合成，使用伯胺、具有手性离去基团的活化酯和缺乏旋转对称性的非手性冠醚。机械平面手性轮烷直接以高达 50% 的对映体过量获得。轮烷通过核磁共振光谱、高分辨质谱、手性高效液相色谱、单晶 X 射线衍射和圆二色性表征。
• Process for preparation of 1,4-benzodioxane derivative
  申请人：Daiso Co., Ltd.

  公开号：US05780650A1

  公开（公告）日：1998-07-14

  A novel process for preparing a 1,4 benzodioxane derivative shown by the formula (1) which is a useful intermediate of circulatory drugs and drugs for psychoneurosis, characterized in sulfonating a phenoxypropanediol with a sulfonyl halide, eliminating the protective group, and then cyclizing the sulfonated compound by treating with a base followed by, if necessary, further sulfonation. ##STR1## In the above formula, R.sup.1 is H, RSO.sub.2, R is alkyl, phenyl which may be substituted with alkyl, R.sup.2, R.sup.3, R.sup.4 are H, halogen, OH, nitro, cyano, formyl, COOH, alkoxycarbonyloxy, alkyl, alkoxy, haloalkyl, N,N-dialkylamino, alkylcarbonyl, alkoxycarbonyl, phenyl which may be substituted by alkyl, etc.22

  一种用于制备1,4-苯二氧杂环丙烷衍生物的新工艺，其化学式如下（1），该衍生物是循环药物和精神神经病药物的有用中间体，其特点在于用磺酰卤化物对苯氧基丙二醇进行磺化，去除保护基，然后通过碱处理使磺化化合物环化，如有必要，进一步进行磺化。在上述化学式中，R.sup.1为H，RSO.sub.2，R为烷基，苯基，可能被烷基取代，R.sup.2，R.sup.3，R.sup.4为H，卤素，羟基，硝基，氰基，甲酰基，羧基，烷氧羰氧基，烷基，烷氧基，卤代烷基，N，N-二烷基氨基，烷基羰基，烷氧羰基，苯基，可能被烷基取代等。
• Preparation and unequivocal identification of the regioisomers of nitrocatechol monobenzyl ether
  作者：Cristiano Bolchi、Francesco Bavo、Marco Pallavicini

  DOI：10.1080/00397911.2017.1334919

  日期：2017.8.18

  The four positional isomers of nitrocatechol monobenzyl ether were prepared as intermediates to nitrobenzodioxanes directly from 2-benzyloxyphenol or, through two-four steps, from catechol. These preparations addressed the issue of the certain identification of the nitration products prescinding from chemical correlation to the synthetic precursors because the positional isomers are very similar for

  摘要 硝基邻苯二酚单苄基醚的四种位置异构体是直接从 2-苄氧基苯酚或通过两到四步从邻苯二酚制备硝基苯并二恶烷的中间体。这些制剂解决了硝化产物的某些鉴定问题，这取决于与合成前体的化学相关性，因为位置异构体在某些性质上非常相似，而且文献中可获得的分析数据在很大程度上是不完整的，不是结论性的。这里提供的 NMR、DSC 和酸度数据明确地区分每种硝基儿茶酚单苄基醚与其区域异构体。图形概要