α-Chlor-p-nitrobenzylisocyanat | 67280-73-3

• 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: α-Chlor-p-nitrobenzylisocyanat
• 英文别名: 1-[Chloro(isocyanato)methyl]-4-nitrobenzene
• CAS: 67280-73-3
• 化学式: C₈H₅ClN₂O₃
• 分子量: 212.592
• InChiKey: FMMNYSYIICOLPV-UHFFFAOYSA-N

物化性质

• 沸点：
  98-100 °C(Press: 0.01 Torr)
• 密度：
  1.42±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  75.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  α-Chlor-p-nitrobenzylisocyanat 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 14.0h， 生成
  参考文献：
  名称：

  Synthesis of Novel Functionalized Derivatives of 5-Nitro-3,4-dihydropyrimidin-2(1H)-one by the Cyclocondensation of 1-Chlorobenzyl Isocyanates with N,S- and N,N-Nitroketeneacetals

  摘要：

  1-氯苄异氰酸酯与S,N-和N,N-硝基烯酰基的环缩合反应被用来合成迄今为止未知的6-硫甲基-5-硝基-3,4-二氢嘧啶-2(1H)-酮、8-硝基-2,3,6,7-四氢咪唑[1,2-c]嘧啶-5(1H)-酮以及9-硝基-1,2,3,4,7,8-六氢-6H-吡咯[1,6-a]嘧啶-6(1H)-酮。对6-硫甲基-5-硝基-3,4-二氢嘧啶-2(1H)-酮中硫甲基的取代生成6-氨基-5-硝基-3,4-二氢嘧啶-2(1H)-酮，该化合物与4-亚氨基-5-硝基-3,4,5,6-四氢嘧啶-2(1H)-酮存在互变异构平衡。如果将所获得的化合物在1,8-二氮双环[5.4.0]十一烯（DBU）存在下于二噁烷中加热，会消除硝基生成取代的4-亚氨基-3,4-二氢嘧啶-2(1H)-酮。

  DOI：

  10.1055/s-2007-965933
• 作为产物：
  描述：

  4-Nitro-benzyliden-bis- 在 五氯化磷 作用下， 以 苯 为溶剂， 反应 4.0h， 生成 α-Chlor-p-nitrobenzylisocyanat
  参考文献：
  名称：

  通过 α-氯苄基异氰酸酯与 N-烷基（芳基）-β-氨基巴豆酸乙酯的环缩合反应方便地合成 N1-取代的 3,4-二氢嘧啶-2（1H）-酮

  摘要：

  使用 α-氯苄基异氰酸酯与 N-烷基（芳基）-β-氨基巴豆酸乙酯的区域选择性环缩合反应，开发了一种合成 N1 取代的 3,4-二氢嘧啶-2(1H)-酮的新方法。以高收率制备了许多通过其他方法难以获得的 N1-芳基和 N1-烷基取代的 Biginelli 化合物。

  DOI：

  10.1055/s-2006-926241

文献信息

• Synthesis of alkyl hexahydropyrazino-[1,2-c]pyrimidine-9-carboxylates
  作者：M. V. Vovk、O. V. Kushnir、N. V. Melˈnichenko、I. F. Tsymbal

  DOI：10.1007/s10593-011-0865-2

  日期：2011.11

  Cyclocondensation of 3-alkoxycarbonylmethylidenepiperazin-2-ones with alpha-chlorobenzyl isocyanates gave alkyl 8-aryl-1,6-dioxo-1,3,4,6,7,8-hexahydro-2H-pyrazino[1,2-c]pyrimidine-9-carboxylates. The use of 1-aryl-2,2,2-trifluoroethyl isocyanates in an analogous cyclization gave 6-aryl-1,8-dioxo-6-trifluoromethyl-1,3,4,6,7,8-hexahydro-2H-pyrazino[1,2-c]pyrimidine-9-carboxylates.
• Reaction of (S)-(+)-4-amino-4-aryl-5,5,5-trifluoropentan-2-ones with α-chlorobenzyl isocyanates. Synthesis of (S)-(+)-4-aryl-6-(2-arylethenyl)-4-trifluoromethyl-3,4-dihydro-pyrimidin-2(1H)-ones
  作者：N. M. Golovach、V. A. Sukach、M. V. Vovk

  DOI：10.1134/s1070428010100222

  日期：2010.10

  (S)-(+)-4-Amino-4-aryl-5,5,5-trifluoropentan-2-ones reacted with 6h-chlorobenzyl isocyanates with formation of (S)-(+)-4-aryl-6-(2-arylethenyl)-4-trifluoromethyl-3,4-dihydropyrimidin-2(1H)-ones.
• Heterocyclizations of functionalized heterocumulenes with C,N-, C,O-, and C,S-binucleophiles: XIII. Synthesis of dialkyl 2-oxo-3-allyl-1,2,3,6-tetrahydropyrimidine-4,5-dicarboxylates and their reaction with arylhydroxymoyl chlorides
  作者：O. V. Kushnir、N. V. Mel’nichenko、M. V. Vovk

  DOI：10.1134/s1070428011110133

  日期：2011.11

  Dialkyl 2-oxo-3-allyl-1,2,3,6-tetrahydropyrimidine-4,5-dicarboxylates obtained by condensation of 1-chlorobenzyl isocyanates with N-allylfumarates reacted regioselectively with arylhydroxymoyl chlorides with the formation of dialkyl 6-aryl-3-[(3-aryl-4,5-dihydro-5-isoxazolyl)methyl]-2-oxo-1,2,3,6-tetrahydropyrimidine-4,5-dicarboxylates.
• Heterocyclization of functionalized heterocumulenes with C,N-, C,O-, and C,S-binucleophiles: VIII. Synthesis of pyrano(chromeno)[3,4-e][1,3]oxazines by condensation of 1-chloroalkyl isocyanates with 4-hydroxy-6-methylpyran-2-one and 4-hydroxycoumarin
  作者：M. V. Vovk、V. A. Sukach、V. I. Dorokhov

  DOI：10.1134/s1070428007080179

  日期：2007.8

  1-Chlorobenzyl isocyanates react with 4-hydroxy-6-methylpyran-2-one and 4-hydroxycoumarin forming 4-aryl-3,4-dihydro-2H,5H-pyrano(chromeno)[3,4-e][1,3]oxazine-2,5-diones. The reaction of 1-aryl-2,2,2-trifluoro-1-chloroethyl isocyanates with the above substrates gives rise to structurally isomeric 2-aryl-2-trifluoromethyl-2,3-dihydro-2H,5H-pyrano(chromeno)[3,4-e][1,3]-oxazine-4,5-diones.
• Heterocyclization of functionalized heterocumulenes with C,N-, C,O-, and C,S-Binucleophiles: XI. Synthesis of dialkyl 2-oxo-3,6-diaryl-1,2,3,6-tetrahydropyrimidine-4,5-dicarboxylates by cyclocondensation of 1-chlorobenzyl isocyanates with dialkyl anilinofumarates
  作者：M. V. Vovk、O. V. Kushnir、V. A. Sukach、I. F. Tsymbal

  DOI：10.1134/s1070428010050209

  日期：2010.5

  1-Chlorobenzyl isocyanates react with N-arylfumarates with the formation of dialkyl 2-oxo-3,6-diaryl-1,2,3,6-tetrahydropyrimidine-4,5-dicarboxylates that on alkaline hydrolysis are converted into 6-alkoxycarbonyl-1,4-diaryl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylic acids. The condensation of 1-chloro-1-phenyl-2,2,2-trifluoroethyl isocyanate with N-arylfumarates results in dialkyl 6-oxo-2,3-diaryl-2-trifluoromethyl-1,2,3,6-tetrahydropyrimidine-4,5-dicarboxylates.