methyl N-[(3-nitrophenyl)methylideneamino]carbamate | 346718-90-9

• 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: methyl N-[(3-nitrophenyl)methylideneamino]carbamate
• CAS: 346718-90-9
• 化学式: C₉H₉N₃O₄
• 分子量: 223.188
• InChiKey: ZTZSBEDAYLMFCQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  96.5
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl N-[(3-nitrophenyl)methylideneamino]carbamate 在 氯 、 三乙胺 作用下， 以 四氢呋喃 、 氯仿 为溶剂， 生成 dimethyl 3,6-di(m-nitrophenyl)-1,4-dihydro-1,2,4,5-tetrazine-1,4-dicarboxylate
  参考文献：
  名称：

  Novel Synthesis, Characterisation and Antitumour Activity of Dimethyl-3,6-di(Aryl)-1,4-Dihydro-1,2,4,5-Tetrazine-1,4-Dicarboxylates

  摘要：

  A series of new dimethyl-3,6-di(aryl)-1,4-dihydro-1,2,4,5-tetrazine-1,4-dicarboxylates were synthesised through an intermolecular cyclisation reaction of methyl N'-(alpha-chloro-substituted benzylidene) hydrazinecarboxylate and triethylamine. Their 1,4-dihydro-s-tetrazine structures were characterised by IR, H-1 NMR, MS, elemental analysis. Their antitumour activities were evaluated in vitro by the SRB method for A-549 cells and the MTT method for P-388 cells. The results show that none of the compounds had a high activity, but the substituents clearly had an effect on their antitumour activity.

  DOI：

  10.3184/174751914x14001747558135
• 作为产物：
  描述：

  在 碘苯二乙酸 作用下， 以 乙腈 为溶剂， 生成 methyl N-[(3-nitrophenyl)methylideneamino]carbamate
  参考文献：
  名称：

  由N'-（芳甲基）肼或1-（芳甲基）-2-（芳基亚甲基）肼无金属合成1,3,4-二唑

  摘要：

  摘要 报道了通过氧化脱氢从N '-（芳基甲基）酰肼或1-（芳基甲基）-2-（芳基亚甲基）肼有效且通用的无金属合成1,3,4-恶二唑。通过用乙腈中的（二乙酰氧基碘）苯处理N '-（芳基甲基）酰肼或用[[]处理1-（芳基甲基）-2-（芳基亚甲基）肼来制备一系列2,5-二取代的1,3,4-恶二唑。甲基叔丁基醚中的双（三氟乙酰氧基）碘]苯。醛N-酰基hydr和醛嗪最初是作为中间体原位生成的。 报道了通过氧化脱氢从N '-（芳基甲基）酰肼或1-（芳基甲基）-2-（芳基亚甲基）肼有效且通用的无金属合成1,3,4-恶二唑。通过用乙腈中的（二乙酰氧基碘）苯处理N '-（芳基甲基）酰肼或用[[]处理1-（芳基甲基）-2-（芳基亚甲基）肼来制备一系列2,5-二取代的1,3,4-恶二唑。甲基叔丁基醚中的双（三氟乙酰氧基）碘]苯。醛N-酰基hydr和醛嗪最初是作为中间体原位生成的。

  DOI：

  10.1055/s-0034-1379974

文献信息

• I₂ mediated synthesis of 5-substituted-3-methyl/benzyl-1,3,4-oxadiazol-2(3H)-ones via sequential condensation/oxidative cyclization and rearrangement
  作者：Shyam Sunder Patel、Nisha Chandna、Shreemoyee Kumar、Nidhi Jain

  DOI：10.1039/c5ob02667a

  日期：——

  A simple and efficient iodine-assisted protocol for the synthesis of 5-substituted-3-methyl/benzyl-1,3,4-oxadiazol-2(3H)-ones has been developed. The reaction involves a sequential condensation followed by tandem oxidative cyclization and rearrangement of readily available methyl/benzyl carbazates and aldehydes as starting substrates. The presence of iodine and base promotes intramolecular C–O bond

  已经开发了一种简单有效的碘辅助方案，用于合成5-取代的3-甲基/苄基-1,3,4-恶二唑-2（3 H）-ones。该反应包括顺序缩合，然后串联氧化环化，以及容易获得的甲基/苄基氨基甲酸酯和醛作为起始底物进行重排。碘和碱的存在会促进分子内C–O键的形成，然后在90°C时在缩合步骤形成的intermediate中间体中，甲基/苄基的Chapman式重排。已采用这种无过渡金属的方法，可在温和条件下以高至优异的收率生成各种恶二唑酮。
• Metal-Free Synthesis of 1,3,4-Oxadiazoles from N′-(Arylmethyl)hydrazides or 1-(Arylmethyl)-2-(arylmethylene)hydrazines
  作者：Zhenhua Shang、Sheng Tan、Qianqian Chu

  DOI：10.1055/s-0034-1379974

  日期：——

  tert-butyl ether. Aldehyde N-acylhydrazones and aldazines were initially generated in situ as intermediates. An efficient and versatile metal-free synthesis of 1,3,4-oxadiazoles from N′-(arylmethyl)hydrazides or 1-(arylmethyl)-2-(arylmeth­ylene)hydrazines through oxidative dehydrogenation is reported. A range of 2,5-disubstituted 1,3,4-oxadiazoles were prepared by treating N′-(arylmethyl)hydrazides with (diacetoxyiodo)benzene

  摘要 报道了通过氧化脱氢从N '-（芳基甲基）酰肼或1-（芳基甲基）-2-（芳基亚甲基）肼有效且通用的无金属合成1,3,4-恶二唑。通过用乙腈中的（二乙酰氧基碘）苯处理N '-（芳基甲基）酰肼或用[[]处理1-（芳基甲基）-2-（芳基亚甲基）肼来制备一系列2,5-二取代的1,3,4-恶二唑。甲基叔丁基醚中的双（三氟乙酰氧基）碘]苯。醛N-酰基hydr和醛嗪最初是作为中间体原位生成的。 报道了通过氧化脱氢从N '-（芳基甲基）酰肼或1-（芳基甲基）-2-（芳基亚甲基）肼有效且通用的无金属合成1,3,4-恶二唑。通过用乙腈中的（二乙酰氧基碘）苯处理N '-（芳基甲基）酰肼或用[[]处理1-（芳基甲基）-2-（芳基亚甲基）肼来制备一系列2,5-二取代的1,3,4-恶二唑。甲基叔丁基醚中的双（三氟乙酰氧基）碘]苯。醛N-酰基hydr和醛嗪最初是作为中间体原位生成的。
• Novel Synthesis, Characterisation and Antitumour Activity of Dimethyl-3,6-di(Aryl)-1,4-Dihydro-1,2,4,5-Tetrazine-1,4-Dicarboxylates
  作者：Lu-Ping Lv、Xiao-Feng Zhou、Hai-Bo Shi、Jian-Rong Gao、Wei-Xiao Hu

  DOI：10.3184/174751914x14001747558135

  日期：2014.6

  A series of new dimethyl-3,6-di(aryl)-1,4-dihydro-1,2,4,5-tetrazine-1,4-dicarboxylates were synthesised through an intermolecular cyclisation reaction of methyl N'-(alpha-chloro-substituted benzylidene) hydrazinecarboxylate and triethylamine. Their 1,4-dihydro-s-tetrazine structures were characterised by IR, H-1 NMR, MS, elemental analysis. Their antitumour activities were evaluated in vitro by the SRB method for A-549 cells and the MTT method for P-388 cells. The results show that none of the compounds had a high activity, but the substituents clearly had an effect on their antitumour activity.