(4-Chlorophenyl)-[3-(methylamino)-4-nitrophenyl]methanone | 914401-83-5

• 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: (4-Chlorophenyl)-[3-(methylamino)-4-nitrophenyl]methanone
• CAS: 914401-83-5
• 化学式: C₁₄H₁₁ClN₂O₃
• 分子量: 290.706
• InChiKey: QVJROYHCEOISFF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  74.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (4-Chlorophenyl)-[3-(methylamino)-4-nitrophenyl]methanone 在 sodium tetrahydroborate 、 氯化亚砜 、 氢气 、 肼 、 sodium nitrite 作用下， 以 水 为溶剂， 生成 (+/-)-6-[(4-chlorophenyl)-hydrazinomethyl)-1-methyl-1H-benzotriazole
  参考文献：
  名称：

  Development Summary towards a Manufacturable Process for R 83842 [(S)-6-[(4-chlorophenyl) (1H-1,2,4-triazol-1-yl)methyl]-1-methyl-1H-benzotriazole]

  摘要：

  A scalable process to produce enantiomeric R 83842, (S)-6-[(4-chlorophenyl) (1H-1,2,4-triazol-1-yl)methyl]-1-methyl-1H-benzotriazole, is developed and described as a lecture* transcript. Cheap and safe reagents have been used. A typical procedure for oxidative destruction of aqueous cyanide waste, and stability data on N-acetyl hydrazine are provided. Special focus is on cost analysis as an important tool in developing performant synthetic methods. The method consists of preparing a chiral monosubstituted hydrazine which is ring closed to the chiral 1-alkylated 1,2,4-triazole title compound.

  DOI：

  10.1021/op990081n
• 作为产物：
  描述：

  对氯苯乙腈 在 苄基三乙基氯化铵 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 生成 (4-Chlorophenyl)-[3-(methylamino)-4-nitrophenyl]methanone
  参考文献：
  名称：

  Development Summary towards a Manufacturable Process for R 83842 [(S)-6-[(4-chlorophenyl) (1H-1,2,4-triazol-1-yl)methyl]-1-methyl-1H-benzotriazole]

  摘要：

  A scalable process to produce enantiomeric R 83842, (S)-6-[(4-chlorophenyl) (1H-1,2,4-triazol-1-yl)methyl]-1-methyl-1H-benzotriazole, is developed and described as a lecture* transcript. Cheap and safe reagents have been used. A typical procedure for oxidative destruction of aqueous cyanide waste, and stability data on N-acetyl hydrazine are provided. Special focus is on cost analysis as an important tool in developing performant synthetic methods. The method consists of preparing a chiral monosubstituted hydrazine which is ring closed to the chiral 1-alkylated 1,2,4-triazole title compound.

  DOI：

  10.1021/op990081n

文献信息

• Benzotriazole Derivatives as Cannabinoid Receptor Antagonists
  申请人：Berwaer Monique Jenny Marie

  公开号：US20080194656A1

  公开（公告）日：2008-08-14

  The present invention relates to a group of benzotriazole derivatives, infra that are potent cannabinoid-CB 1 modulators (known as antagonists or inverse agonists), useful in the treatment obesity, psychiatric and neurological disorders, as well as other diseases involving cannabinoid-CB 1 neurotransmission (Current Opinion in Drug Discovery & Development 2004 7(4):498-506) the pharmaceutically acceptable acid addition salts and stereoisomeric forms thereof, wherein R 1 is hydrogen, halo, trifluoromethyl, C 1-4 alkyl, C 1-4 alkyloxy- or C 1-4 alkyloxycarbonyl; R 2 is hydrogen, phenyl, C 3-7 cycloalkyl or C 1-6 alkyl optionally substituted with Ar 1 ; R 3 is hydrogen, hydroxyl or C 1-6 alkyl; Ar 1 is phenyl or phenyl substituted with up to three halo substituents; and Het represents a monocyclic 5 or 6 membered partially saturated or aromatic heterocycle selected from furanyl, thienyl, pyrrolyl, oxazolyl, thiazolyl, imidazolyl, pyrazolyl, isoxazolyl, isothiazolyl, oxadiazolyl, triazolyl, thiadiazolyl, pyrimidinyl, pyridinyl, pyrazinyl, triazinyl, pyridazinyl, 2H-pyranyl or 4H-pyranyl wherein said heterocycle is optionally substituted with C 1-6 alkyl;

  本发明涉及一组苯并三唑衍生物，其为有效的大麻素-CB1调节剂（也称为拮抗剂或反向激动剂），可用于治疗肥胖症、精神和神经疾病以及涉及大麻素-CB1神经递质的其他疾病（《药物发现与开发的现状》2004年7（4）：498-506），包括其药学上可接受的酸加合物盐和立体异构体形式。其中，R1为氢、卤素、三氟甲基、C1-4烷基、C1-4烷氧基或C1-4烷氧羰基；R2为氢、苯基、C3-7环烷基或C1-6烷基，可选地取代Ar1；R3为氢、羟基或C1-6烷基；Ar1为苯基或取代了最多三个卤素基团的苯基；Het表示从呋喃基、噻吩基、吡咯基、噁唑基、噻唑基、咪唑基、吡唑基、异噁唑基、异噻唑基、噁二唑基、三唑基、噻二唑基、嘧啶基、吡啶基、吡嗪基、三嗪基、吡啶嗪基、2H-吡喃基或4H-吡喃基中选择的一个单环5或6成员部分饱和或芳香杂环，其中所述杂环可选地取代C1-6烷基。
• Organic Process Research amp; Development 2000, 4, 162-166
  作者：

  DOI：——

  日期：——
• Development Summary towards a Manufacturable Process for R 83842 [(<i>S</i>)-6-[(4-chlorophenyl) (1H-1,2,4-triazol-1-yl)methyl]-1-methyl-1H-benzotriazole]
  作者：A. G. M. De Knaep、A. M. J. Vandendriessche、D. J. E. Daemen、J. J. Dingenen、K. D. Laenen、R. L. Nijs、F. L. J. Pauwels、D. F. Van den Heuvel、F. J. Van der Eycken、R. W. E. Vanierschot、G. M. L. W. van Laar、W. L. A. Verstappen、B. L. A. Willemsens

  DOI：10.1021/op990081n

  日期：2000.5.1

  A scalable process to produce enantiomeric R 83842, (S)-6-[(4-chlorophenyl) (1H-1,2,4-triazol-1-yl)methyl]-1-methyl-1H-benzotriazole, is developed and described as a lecture* transcript. Cheap and safe reagents have been used. A typical procedure for oxidative destruction of aqueous cyanide waste, and stability data on N-acetyl hydrazine are provided. Special focus is on cost analysis as an important tool in developing performant synthetic methods. The method consists of preparing a chiral monosubstituted hydrazine which is ring closed to the chiral 1-alkylated 1,2,4-triazole title compound.