tert-butyl N-(2-isocyano-4,5-dimethylphenyl)carbamate | 1383606-13-0

• 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: tert-butyl N-(2-isocyano-4,5-dimethylphenyl)carbamate
• CAS: 1383606-13-0
• 化学式: C₁₄H₁₈N₂O₂
• 分子量: 246.309
• InChiKey: BREGNXBFGJTAFY-UHFFFAOYSA-N

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：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  42.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  tert-butyl N-(2-isocyano-4,5-dimethylphenyl)carbamate 在 叠氮基三甲基硅烷 、 三氟乙酸 作用下， 以 2,2,2-三氟乙醇 、 1,2-二氯乙烷 为溶剂， 反应 24.17h， 生成 8,9-dimethyl-4-(pyrrolidin-1-yl)-4H-benzo[b]tetrazolo[1,5-d][1,4]diazepin-5(6H)-one
  参考文献：
  名称：

  Synthesis of tetrazolo-fused benzodiazepines and benzodiazepinones by a two-step protocol using an Ugi-azide reaction for initial diversity generation

  摘要：

  A two-step strategy for the synthesis of arrays of tricyclic tetrazolo-fused benzodiazepines and benzodiazepinones has been investigated. The protocol uses ortho-N-Boc phenylisocyanides and phenylglyoxaldehydes or ethyl glyoxylate in the four-component Ugi-azide reaction to afford MCR (MultiComponent Reactions) derived adducts equipped with the desired diversity inputs. A subsequent acidic treatment (TFA/DCE) allows a simultaneous deprotection-cyclization leading to the final products. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.04.068

文献信息

• Expeditious Routes to Polycyclic Molecular Frameworks via One-Pot, Two-Step Ugi Ring-Closing Sequences
  作者：Christopher Hulme、Zhigang Xu、Fabio De Moliner、Alexandra Cappelli、Muhammed Ayaz

  DOI：10.1055/s-0033-1340219

  日期：——

  Ugi condensation between ethyl glyoxylate, isonitriles, N -Boc-α-amino acids, and mono - N -Boc-protected diamines followed by a series of acid-promoted cyclization steps in a one-pot fashion is reported. This process allows for the assembly of complex polycyclic structures by means of just two simple synthetic operations and a single chromatographic purification in high overall yields. Of note, the

  一个非常通用和强大的多组分反应方案，包括乙醛酸乙酯、异腈、N-Boc-α-氨基酸和单-N-Boc-保护的二胺之间的 Ugi 缩合，然后是一系列酸促进的环化步骤-锅时尚报道。该过程允许通过仅两个简单的合成操作和单次色谱纯化以高总产率组装复杂的多环结构。值得注意的是，据报道，第一个支架源自高度选择性的闭环事件序列，涉及三个内部氨基亲核试剂。
• Facile One-Pot Synthesis of Benzimidazole and Quinoxalin-2(1H)-one Scaffolds via Two-Component Coupling Reaction, Deprotection, and Intermolecular Cyclization
  作者：Jin Zhang、Zhi-Gang Xu、Zhong-Zhu Chen、Ying Tang、Lei Zuo、Dian-Yong Tang

  DOI：10.1055/s-0034-1379016

  日期：——

  Two scaffolds, namely benzimidazole and quinoxalin2(1H)-one, were synthesized by treating 2-(N-Boc-amino)phenylisocyanide (Boc: tert-butoxycarbonyl) with carboxylic acids and glyoxylic acids, respectively. The target compounds were generated directly after two-component coupling, deprotection, and intermolecular cyclization.