meso-1,2-bis(3-methylphenyl)-1,2-ethanediamine | 117106-34-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: meso-1,2-bis(3-methylphenyl)-1,2-ethanediamine
• 英文别名: (1R,2S)-1,2-bis(3-methylphenyl)ethane-1,2-diamine
• CAS: 117106-34-0
• 化学式: C₁₆H₂₀N₂
• 分子量: 240.348
• InChiKey: ZZCFHMGJMQEYQJ-IYBDPMFKSA-N

物化性质

• 沸点：
  383.8±37.0 °C(Predicted)
• 密度：
  1.071±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  52
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  meso-1,2-bis(3-methylphenyl)-1,2-ethanediamine 、 氯甲酸烯丙酯 在 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以46%的产率得到(1S,2R)-N-2-amino-1,2-bis(3-methylphenyl)ethylallyl carbamate
  参考文献：
  名称：

  Lipase-catalyzed desymmetrization of meso-1,2-diaryl-1,2-diaminoethanes

  摘要：

  The synthesis and enzyme-catalyzed desymmetrization of meso-1,2-diaryl-1,2-diaminoethanes have been investigated. A family of aromatic meso-1,2-diamines, containing different substitution patterns in the aromatic ring, was first prepared and then desymmetrized enantioselectively using lipases as biocatalysts. Selective alkoxycarbonylation of one of the amino groups was achieved using allyl carbonates, isolating the corresponding allyl monocarbamates with moderate to high enantiomeric excess at 45 degrees C. Candida antarctica lipase types A (CAL-A) and B (CAL-B) displayed the best activities and stereopreferences, with a dramatic influence being observed depending on the diamine structure. Non substituted and para-substituted aryldiamines led to the formation of allyl carbamates with good enantiomeric excess, using CAL-A for the less hindered substrates and CAL-B for the more hindered ones. On the other hand meta- and ortho-derivatives afforded low or negligible conversions and selectivities, respectively. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2014.01.007
• 作为产物：
  描述：

  3-甲基苯甲醛 在 硫酸 、 水 作用下， 反应 15.0h， 以78%的产率得到meso-1,2-bis(3-methylphenyl)-1,2-ethanediamine
  参考文献：
  名称：

  Lipase-catalyzed desymmetrization of meso-1,2-diaryl-1,2-diaminoethanes

  摘要：

  The synthesis and enzyme-catalyzed desymmetrization of meso-1,2-diaryl-1,2-diaminoethanes have been investigated. A family of aromatic meso-1,2-diamines, containing different substitution patterns in the aromatic ring, was first prepared and then desymmetrized enantioselectively using lipases as biocatalysts. Selective alkoxycarbonylation of one of the amino groups was achieved using allyl carbonates, isolating the corresponding allyl monocarbamates with moderate to high enantiomeric excess at 45 degrees C. Candida antarctica lipase types A (CAL-A) and B (CAL-B) displayed the best activities and stereopreferences, with a dramatic influence being observed depending on the diamine structure. Non substituted and para-substituted aryldiamines led to the formation of allyl carbamates with good enantiomeric excess, using CAL-A for the less hindered substrates and CAL-B for the more hindered ones. On the other hand meta- and ortho-derivatives afforded low or negligible conversions and selectivities, respectively. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2014.01.007

文献信息

• Heterocyclic compounds as P2X7 ion channel blockers
  申请人：Shum Patrick

  公开号：US20050026916A1

  公开（公告）日：2005-02-03

  The present invention relates to a novel series of 4,5-diphenyl-2-amino-4,5-dihydro-imidazole derivatives of the formula II: wherein R, R 1 , R 2 , R 3 , R 4 , R 5 , X and Y are as defined herein. This invention also relates to methods of making these compounds. The compounds of this invention are P2X7 ion channel blockers and are therefore useful as pharmaceutical agents, especially in the treatment and/or prevention of a variety of diseases having an inflammatory component, including inflammatory bowel disease, rheumatoid arthritis and disease conditions associated with the central nervous system, such as stroke, Alzheimer's disease, etc.

  本发明涉及一种新的4,5-二苯基-2-氨基-4,5-二氢咪唑衍生物系列，其化学式为II： 其中R、R1、R2、R3、R4、R5、X和Y如本文所定义。本发明还涉及制备这些化合物的方法。本发明的化合物是P2X7离子通道阻断剂，因此在作为药用剂方面具有用途，特别是在治疗和/或预防具有炎症成分的各种疾病方面，包括炎症性肠病、类风湿关节炎以及与中枢神经系统相关的疾病状况，如中风、阿尔茨海默病等。
• HETEROCYCLIC COMPOUNDS AS P2X7 ION CHANNEL BLOCKERS
  申请人：SHUM Patrick

  公开号：US20080132550A1

  公开（公告）日：2008-06-05

  The present invention relates to a novel series of 4,5-diphenyl-2-amino-4,5-dihydro-imidazole derivatives of the formula II: wherein R, R 1 , R 2 , R 3 , R 4 , R 5 , X and Y are as defined herein. This invention also relates to methods of making these compounds. The compounds of this invention are P2X7 ion channel blockers and are therefore useful as pharmaceutical agents, especially in the treatment and/or prevention of a variety of diseases having an inflammatory component, including inflammatory bowel disease, rheumatoid arthritis and disease conditions associated with the central nervous system, such as stroke, Alzheimer's disease, etc.

  本发明涉及一种新的4,5-二苯基-2-氨基-4,5-二氢咪唑衍生物系列，其化学式为II：其中R、R1、R2、R3、R4、R5、X和Y如本文所定义。本发明还涉及制备这些化合物的方法。本发明的化合物是P2X7离子通道阻滞剂，因此在治疗和/或预防具有炎症成分的多种疾病方面，包括炎症性肠病、类风湿性关节炎以及与中枢神经系统相关的疾病状态，如中风、阿尔茨海默病等方面，具有药物学上的用途。
• 4,5-DIHYDRO-IMIDAZOLE AS P2X7 ION CHANNEL BLOCKERS
  申请人：Aventis Pharmaceuticals, Inc.

  公开号：EP1651613A1

  公开（公告）日：2006-05-03
• US7326792B2
  申请人：——

  公开号：US7326792B2

  公开（公告）日：2008-02-05
• US7741493B2
  申请人：——

  公开号：US7741493B2

  公开（公告）日：2010-06-22