N-benzyloxy-nicotinamide | 25983-73-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: N-benzyloxy-nicotinamide
• 英文别名: N-(benzyloxy)nicotinamide；N-phenylmethoxypyridine-3-carboxamide
• CAS: 25983-73-7
• 化学式: C₁₃H₁₂N₂O₂
• mdl: MFCD06795149
• 分子量: 228.25
• InChiKey: RAXWUDYAOLECEY-UHFFFAOYSA-N

物化性质

• 熔点：
  72-73 °C
• 密度：
  1.200±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.076
• 拓扑面积：
  51.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-benzyloxy-nicotinamide 在 碘 、 sodium carbonate 作用下， 以 乙腈 为溶剂， 反应 5.0h， 以59%的产率得到烟酸苄酯
  参考文献：
  名称：

  无金属碘介导的异羟肟酸酯转化为酯

  摘要：

  摘要 使用分子碘作为试剂，使用一种新颖但尚未探索的苍鹭型重排，实现了无金属、无氧化剂和无添加剂的异羟肟酸酯转化为酯。反应以几乎相同的便利与具有给电子或吸电子取代基的底物进行。类似地，α,β-不饱和和空间位阻的邻位取代异羟肟酸酯也能顺利进行所需的转化。图形概要

  DOI：

  10.1080/00397911.2020.1737130
• 作为产物：
  描述：

  烟酸 、 苄氧基胺盐酸盐 在 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N-甲基吗啉 作用下， 以 二氯甲烷 为溶剂， 反应 16.25h， 以79%的产率得到N-benzyloxy-nicotinamide
  参考文献：
  名称：

  无金属碘介导的异羟肟酸酯转化为酯

  摘要：

  摘要 使用分子碘作为试剂，使用一种新颖但尚未探索的苍鹭型重排，实现了无金属、无氧化剂和无添加剂的异羟肟酸酯转化为酯。反应以几乎相同的便利与具有给电子或吸电子取代基的底物进行。类似地，α,β-不饱和和空间位阻的邻位取代异羟肟酸酯也能顺利进行所需的转化。图形概要

  DOI：

  10.1080/00397911.2020.1737130

文献信息

• Design, synthesis and utilization of a novel coupling reagent for the preparation of O-alkyl hydroxamic acids
  作者：Nagnnath D. Kokare、Rahul R. Nagawade、Vipul P. Rane、Devanand B. Shinde

  DOI：10.1016/j.tetlet.2007.04.058

  日期：2007.6

  An efficient novel reagent, phosphoric acid diethyl ester 2-phenyl-benzimidazol-1-yl ester, was designed, and synthesized and its applicability was demonstrated for the preparation of O-alkyl hydroxamic acids. The O-alkyl hydroxamic acids of N-protected amino acids were also synthesized. The enantiomeric purity of the synthesized compounds were measured using chiral HPLC and the degree of racemization

  设计合成了一种高效的新型试剂磷酸二乙酯2-苯基-苯并咪唑-1-基酯，证明了其在制备O-烷基异羟肟酸中的适用性。还合成了N-保护的氨基酸的O-烷基异羟肟酸。使用手性HPLC测量合成化合物的对映体纯度，发现外消旋度可忽略不计。
• <i>N</i>-[(Diphenoxyphosphoryl)oxy]-2-phenyl-1<i>H</i>-benzimidazole as a versatile reagent for synthesis<i>O</i>-alkylhydroxamic acids
  作者：Nagnnath D. Kokare、Devanand B. Shinde

  DOI：10.1002/jhet.5570450406

  日期：2008.7

  Highly efficient reagent, N-[(diphenoxyphosphoryl)oxy]-2-phenyl-1H-benzimidazole was synthesized and its applicability was demonstrated for the synthesis of O-alkyl hydroxamic acids. The efficiency of the reagent was evaluated through the synthesis of range of O-alkyl hydroxamic acids from aromatic carboxylic acids as well as N-protected amino acids. The enatiomeric purity of synthesized compounds

  合成了高效试剂N -[（二苯氧基磷酰基）氧基] -2-苯基-1 H-苯并咪唑，并证明了其在合成O-烷基异羟肟酸中的适用性。通过从芳族羧酸以及N-保护的氨基酸合成范围广泛的O-烷基异羟肟酸来评估试剂的效率。使用手性HPLC测定合成化合物的对映体纯度，发现发生的外消旋度可忽略不计。
• Hydroximic acid derivatives, pharmaceutical compositions containing
  申请人：BIOREX Kutato es Fejleszto Rt.

  公开号：US05919796A1

  公开（公告）日：1999-07-06

  Hydroximic acid derivatives possess anti-ischemic effects, and therefore, they are useful for treating ischemic states and diseases, such as myocardial ischemia (which may be induced by occlusion of coronary arteries). These derivatives include compounds of formula (I): ##STR1## wherein: X represents a halogen; Z represents an aromatic group, a pyridinyl group, a picolyl group, or a lutidyl group; and R represents an --A--N(R.sub.1)R.sub.2 group, wherein: R.sub.1 and R.sub.2 represent, independently from each other, hydrogen or an alkyl group; or R.sub.1 and R.sub.2, together with the adjacent nitrogen atom, form a 5- to 7-membered, saturated heterocyclic group optionally containing an additional nitrogen, oxygen, or sulfur atom, the heterocyclic group optionally being substituted by at least one alkyl group; and A represents a straight or branched chain alkylene group, as well as pharmaceutically acceptable acid addition salts thereof. The invention further relates to processes for preparing the above noted compounds, and pharmaceutical compositions containing these compounds or their pharmaceutically acceptable acid addition salts as an active ingredient. Additionally, the invention relates to intermediate compounds of formula II used in preparing the compounds of formula I. Formula II is as follows: ##STR2## In formula II, the variables Z and R have the same definitions provided above.

  羟肟酸衍生物具有抗缺血作用，因此它们可用于治疗缺血状态和疾病，如心肌缺血（可能由冠状动脉阻塞引起）。这些衍生物包括式（I）的化合物：##STR1##其中：X代表卤素；Z代表芳香基，吡啶基，吡哆基或吕替基；R代表--A--N(R.sub.1)R.sub.2基团，其中：R.sub.1和R.sub.2各自独立地代表氢或烷基；或R.sub.1和R.sub.2与相邻的氮原子一起形成5-至7-成员饱和杂环基团，该杂环基团可选地包含一个额外的氮、氧或硫原子，该杂环基团可选地被至少一个烷基取代；A代表直链或支链烷基，以及其药学上可接受的酸加成盐。本发明还涉及制备上述化合物的过程，以及含有这些化合物或其药学上可接受的酸加成盐作为活性成分的药物组合物。此外，本发明还涉及用于制备式I化合物的式II中间体化合物。式II如下：##STR2## 在式II中，变量Z和R具有上述相同的定义。
• One-Step Synthesis of <i>O</i>-Benzyl Hydroxamates from Unactivated Aliphatic and Aromatic Esters
  作者：Arnaud Gissot、Alessandro Volonterio、Matteo Zanda

  DOI：10.1021/jo0509713

  日期：2005.8.1

  [GRAPHICS]We have developed a simple and high yielding one-step method for the synthesis of hydroxamate derivatives directly from a broad range of unactivated esters and the anion of O-benzyl-hydroxylamine generated in situ. The reaction takes place in minutes at -78 degrees C. Very importantly, the method was successfully employed with enolizable esters, including chiral alpha-amino acid esters and peptides, with no trace of racemization/epimerization at the a carbon detected.
• NOVEL HYDROXIMIC ACID DERIVATIVES, PHARMACEUTICAL COMPOSITIONS CONTAINING THEM AND PROCESS FOR PREPARING SAME
  申请人：BIOREX KUTATO ES FEJLESZTÖ RT.

  公开号：EP0758315B1

  公开（公告）日：1998-08-26