N-(2-azido-4-chlorobenzoyl)-ε-caprolactam | 328571-62-6

• 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: N-(2-azido-4-chlorobenzoyl)-ε-caprolactam
• 英文别名: 1-(2-Azido-4-chlorobenzoyl)azepan-2-one
• CAS: 328571-62-6
• 化学式: C₁₃H₁₃ClN₄O₂
• 分子量: 292.725
• InChiKey: UBUPEFVQGRVRIK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  51.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(2-azido-4-chlorobenzoyl)-ε-caprolactam 在 三氯化铁 、 sodium iodide 作用下， 以 乙腈 为溶剂， 以96%的产率得到3-chloro-7,8,9,10-tetrahydroazepino[2,1-b]quinazolin-12(6H)-one
  参考文献：
  名称：

  轻度有效地将叠氮化物还原为胺：稠合的[2,1- b ]喹唑啉酮的合成

  摘要：

  FeCl 3 / NaI已用于有效还原各种叠氮化物。该方法在硝基官能团存在的情况下是选择性的，并且已经扩展为合成稠合的[ 2,1- b ]喹唑啉酮环系统，例如脱氧维辛酮。

  DOI：

  10.1016/s0040-4039(02)01454-5
• 作为产物：
  描述：

  2-羧基-5-氯苯基叠氮化物 在 氯化亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 7.0h， 生成 N-(2-azido-4-chlorobenzoyl)-ε-caprolactam
  参考文献：
  名称：

  Chemoenzymatic Synthesis of Pyrrolo[2,1-b]quinazolinones:  Lipase-Catalyzed Resolution of Vasicinone

  摘要：

  A facile synthesis of bronchodilatory pyrrolo [2,1-b] quinazoline alkaloids by azidoreductive cyclization strategy employing TMSCl-NaI and bakers' yeast is described. Both the chemical and enzymatic methods are mild and take place at room temperature in good yields. Further, synthesis and resolution of vasicinone has been carried out by employing different lipases. It has been observed that lipase PS provides acetate of (S)-vasicinone in 98% ee.

  DOI：

  10.1021/jo0011484

文献信息

• Mild and efficient reduction of azides to amines: synthesis of fused [2,1-b]quinazolinones
  作者：Ahmed Kamal、K.Venkata Ramana、Hari Babu Ankati、A.Venkata Ramana

  DOI：10.1016/s0040-4039(02)01454-5

  日期：2002.9

  FeCl3/NaI has been employed for an efficient reduction of a variety of azides. This method is selective in the presence of a nitro functionality and has been extended for the synthesis of fused [2,1-b]quinazolinone ring systems such as deoxyvasicinone.

  FeCl 3 / NaI已用于有效还原各种叠氮化物。该方法在硝基官能团存在的情况下是选择性的，并且已经扩展为合成稠合的[ 2,1- b ]喹唑啉酮环系统，例如脱氧维辛酮。
• Chemoenzymatic Synthesis of Pyrrolo[2,1-<i>b</i>]quinazolinones:  Lipase-Catalyzed Resolution of Vasicinone
  作者：Ahmed Kamal、K. Venkata Ramana、Maddamsetty V. Rao

  DOI：10.1021/jo0011484

  日期：2001.2.1

  A facile synthesis of bronchodilatory pyrrolo [2,1-b] quinazoline alkaloids by azidoreductive cyclization strategy employing TMSCl-NaI and bakers' yeast is described. Both the chemical and enzymatic methods are mild and take place at room temperature in good yields. Further, synthesis and resolution of vasicinone has been carried out by employing different lipases. It has been observed that lipase PS provides acetate of (S)-vasicinone in 98% ee.
• Reversible P(III)/P(V) Redox: Catalytic Aza-Wittig Reaction for the Synthesis of 4(3<i>H</i>)-Quinazolinones and the Natural Product Vasicinone
  作者：Long Wang、Ying Wang、Min Chen、Ming-Wu Ding

  DOI：10.1002/adsc.201300950

  日期：2014.3.24

  The catalytic aza‐Wittig reaction based on a phosphine/phosphine oxide catalytic cycle is reported. The by‐product triphenylphosphine oxide (Ph3PO) was reduced in situ to triphenylphosphine (Ph3P) with good chemselectivity so that the aza‐Wittig reaction can be accomplished by using merely a catalytic amount of triphenylphosphine. The reaction has been demonstrated in an efficient synthesis of 4(3H)‐quinazolinones

  报道了基于膦/氧化膦催化循环的催化氮杂-维蒂希反应。副产物三苯基膦氧化物（Ph 3 PO）以良好的化学选择性被原位还原为三苯基膦（Ph 3 P），因此仅使用催化量的三苯基膦即可完成氮杂-维蒂希反应。该反应已被证明在的4（3一种高效合成ħ）-quinazolinones和天然产物（小号）-vasicinone以高产率，通过使用三苯基膦（5％）的催化量和四甲基二硅氧烷/四异丙氧基钛[TMDS / Ti（Oi- Pr）4 ]还原剂系统（81–95％的收率和> 99％的ee）。