1-benzoyl-1,2-dihydrodeoxyvasicinone | 133566-53-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 1-benzoyl-1,2-dihydrodeoxyvasicinone
• 英文别名: 4-(phenylcarbonyl)-2,3,3a,4-tetrahydropyrrolo[2,1-b]quinazolin-9(1H)-one；4-benzoyl-1,2,3,3a-tetrahydropyrrolo[2,1-b]quinazolin-9-one
• CAS: 133566-53-7
• 化学式: C₁₈H₁₆N₂O₂
• 分子量: 292.337
• InChiKey: INZVVBQHEVVWTG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  40.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  脱氧鸭嘴花碱酮 在 sodium tetrahydroborate 、 三乙胺 作用下， 以 乙醇 、 苯 为溶剂， 生成 1-benzoyl-1,2-dihydrodeoxyvasicinone
  参考文献：
  名称：

  Synthesis, methylation, and acylation of 1,2-dihydrodeoxyvasicinones and their homologs

  摘要：

  DOI：

  10.1007/bf00601291

文献信息

• 1-Acyldeoxyvasicinone salts as effective intermediate C-and N-acylating agents for alkaloids and amino acids
  作者：Kh. M. Shakhidoyatov、G. P. Genjemuratova、E. Oripov

  DOI：10.1007/s10600-006-0261-9

  日期：2006.11

  The reaction of deoxyvasicinone with acid chlorides of aliphatic (acetylbromide) and aromatic (benzoyl-, o-, p-methoxy-, p-nitrobenzoylchlorides) acids was studied. It was shown that 1-deoxyvasicinone salts were formed at room temperature; α-aroyloxymethylidenedeoxyvasicinones, in the presence of triethylamine at 80–85°C. It was found that acid chlorides cause 1-acyldeoxyvasicinone salts to transform into α-hydroxy-or α-aroyloxyarylidenedeoxyvasicinones, which indirectly confirmed their acylating properties. It was found that 1-acyldeoxyvasicinone salts were effective acylating agents for alkaloids (cytisine, 1,2-dihydrodeoxyvasicinone) and amino acids (glycine, β-alanine, α-aminobutyric acid) and can be used to acylate primary and secondary aliphatic and heterocyclic amines.

  研究了脱氧紫堇酮与脂肪族（乙酰溴）和芳香族（苯甲酰、邻、对甲氧基、对硝基苯甲酰氯）羧酸酰氯的反应。结果表明，在室温下形成1-脱氧紫堇酮盐；在三乙胺存在下，80-85°C时形成α-芳酰氧甲叉脱氧紫堇酮。研究发现，酰氯引起1-酰基脱氧紫堇酮盐转化为α-羟基或α-芳酰氧芳叉脱氧紫堇酮，间接证实了它们的酰化性质。发现1-酰基脱氧紫堇酮盐对生物碱（金雀花碱、1,2-二氢脱氧紫堇酮）和氨基酸（甘氨酸、β-丙氨酸、α-氨基丁酸）是有效的酰化剂，并可用于酰化脂肪族和杂环的一级和二级胺。
• SHAXIDOYATOV, X. M.;BELOVA, G. A., XIMIYA PRIROD. SOED.,(1990) N, S. 659-663
  作者：SHAXIDOYATOV, X. M.、BELOVA, G. A.

  DOI：——

  日期：——
• Synthesis, methylation, and acylation of 1,2-dihydrodeoxyvasicinones and their homologs
  作者：Kh. M. Shakhidoyatov、G. A. Belova

  DOI：10.1007/bf00601291

  日期：1990.9