1-N-(3'-methoxyphenyl)-4-N-methyl-1-4-diaza-cyclohexane | 57318-64-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: 1-N-(3'-methoxyphenyl)-4-N-methyl-1-4-diaza-cyclohexane
• 英文别名: 1-(3'-methoxyphenyl)-4-methylpiperazine；1-(3-methoxyphenyl)-4-methylpiperazine；1-(3-methoxy-phenyl)-4-methyl-piperazine；4-Methyl-1-<3-methoxy-phenyl>-piperazin；1-(3-Methoxyphenyl)-4-methyl-piperazine
• CAS: 57318-64-6
• 化学式: C₁₂H₁₈N₂O
• 分子量: 206.288
• InChiKey: GIBGGWFWTSZAGO-UHFFFAOYSA-N

物化性质

• 沸点：
  106-108 °C(Press: 0.3 Torr)
• 密度：
  1.048±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  15.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-N-(3'-methoxyphenyl)-4-N-methyl-1-4-diaza-cyclohexane 在 40percent aq. HBr 作用下， 反应 60.0h， 以88%的产率得到3-(4-methylpiperazin-1-yl)phenol
  参考文献：
  名称：

  Structure−Affinity Relationships of a Unique Nicotinic Ligand:  N-Dimethyl-N⁴-phenylpiperazinium Iodide (DMPP)

  摘要：

  DMPP is a well-known nicotinic agonist that does not fit any proposed pharmacophore for nicotinic binding and represents a unique ligand among the hundreds of nicotinic agonists studied in the past decades. A systematic modulation of the chemical structure of DMPP, aimed to establish its structure-affinity relationships, is reported. The research has allowed to identify molecules such as I Ic, 13c, 14c, and 28c, with affinities for alpha (4)beta (2) receptors in the low nanomolar range, some 2 orders of magnitude lower than the lead compound. The agonistic properties of the most interesting compounds have been assessed by measuring their analgesic activity on mice (hot-plate test). Another result of the research was the identification of DMPP analogues, such as 3a (K-i = 90 nM) and 14b (K-i = 180 nM), that maintain affinity for the central nicotinic receptor when the ammonium function is changed into an aminic one and are therefore possible leads for drug development in neurodegenerative diseases.

  DOI：

  10.1021/jm010901y
• 作为产物：
  描述：

  N-甲基哌嗪 、 间氟苯甲醚 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 生成 1-N-(3'-methoxyphenyl)-4-N-methyl-1-4-diaza-cyclohexane
  参考文献：
  名称：

  Direct substitution of aromatic ethers by lithium amides. A new aromatic amination reaction

  摘要：

  Reaction of lithiated dialkylamines with methoxy aromatics in refluxing THF leads to products resulting from a direct ipso-substitution. Especially with lithiated secondary amines high conversions and selectivities are achieved. Sulfonyl-substituted aromatics react equally well, but halogenated aromatics give rise to side-products arising from a competing pathway via aryne intermediates. The scope and mechanistic implications of this novel nucleophilic amination reaction are described.

  DOI：

  10.1021/jo00071a019

文献信息

• Novel Anthra [1, 2-d]imidazole-6,11-dione Derivatives, Preparation Method and application thereof
  申请人：HUANG Hsu-Shan

  公开号：US20110207719A1

  公开（公告）日：2011-08-25

  A series of novel anthra[1,2-d]imidazole-6,11-dione derivatives, and the preparation method and application of said derivatives, wherein said application includes a pharmaceutical composition containing said derivatives for treating cancer, and said application involves effects of said derivatives for inhibiting telomerase activity, inhibiting the growth of cancer cell, treating cancer and the like.

  一系列新型蒽[1,2-d]咪唑-6,11-二酮衍生物，以及所述衍生物的制备方法和应用，其中所述应用包括含有所述衍生物的用于治疗癌症的药物组合物，所述应用涉及所述衍生物抑制端粒酶活性、抑制癌细胞生长、治疗癌症等效果。
• Transition metal-free amination of aryl halides—A simple and reliable method for the efficient and high-yielding synthesis of N-arylated amines
  作者：Jeanne L. Bolliger、Christian M. Frech

  DOI：10.1016/j.tet.2008.11.072

  日期：2009.2

  intermediates is not necessary, allowing the synthesis of pyridine-2,6-diamines in ‘one-pot’. However, catalysts are in many cases not required to efficiently and selectively couple aryl halides with amines, making transition metal-free versions of the Buchwald–Hartwig reaction extremely attractive for the synthesis of N-arylated amines with substrates containing substituents on the aryl halide, which either promote

  提出了一种简单，可靠的反应方案，用于在无过渡金属的反应条件下，由芳基卤化物与各种（也是位阻的）胺反应衍生而来的各种N-芳基化胺的清洁，快速和高产率合成。二恶烷和KN（Si（CH 3）3）2被发现是该转化的理想溶剂和基础。观察到的转化率和产率极好，并且在大多数反应中进行的反应明显高于其催化形式的反应。此外，几乎可以选择性合成6-卤代吡啶-2-胺和不对称吡啶-2,6-二胺（分别来自2,6-二溴吡啶和2,6-二氯吡啶的连续反应）。在非常短的反应时间内即可获得定量收率（相对于2,6-二卤代吡啶）。不需要纯化6-卤代吡啶-2-胺中间体，从而可以在“一锅法”中合成吡啶-2,6-二胺。但是，催化剂在许多情况下不是有效地和选择性地使芳基卤化物与胺偶联，使无过渡金属形式的Buchwald-Hartwig反应对于合成N-芳基化胺（在芳基卤化物上具有取代基的底物）极具吸引力，这会促进区域选择性和/或不需要区域选择性胺化。
• Gonadotropin Releasing Hormone Receptor Antagonist, Preparation Method Thereof And Pharmaceutical Composition Comprising The Same
  申请人：Kim Seon Mi

  公开号：US20130137661A1

  公开（公告）日：2013-05-30

  Disclosed are compounds useful as gonadotrophin-releasing hormone (“GnRH”) receptor antagonist.

  披露了作为促性腺激素释放激素（“GnRH”）受体拮抗剂有用的化合物。
• Novel Aryl Piperazine Derivatives With Medical Utility
  申请人：Campiani Giuseppe

  公开号：US20090238761A1

  公开（公告）日：2009-09-24

  This invention provides novel aryl piperazine derivatives having medical utility, in particular as modulators of dopamine and serotonin receptors, preferably the D 3 , D 2 -like and 5-HT 2 receptor subtypes, and in particular useful for the treatment of neuropsychiatric disorders incl. schizophrenia.

  这项发明提供了具有医疗效用的新型芳基哌嗪衍生物，特别是作为多巴胺和5-羟色胺受体的调节剂，优选为D3、D2样和5-HT2受体亚型，特别适用于治疗包括精神分裂症在内的神经精神障碍。
• NOVEL INDENO[1,2-c]QUINOLIN-11-ONE DERIVATIVES, PREPARATION METHOD AND APPLICATION THEREOF
  申请人：National Defense Medical Center

  公开号：US20150197492A1

  公开（公告）日：2015-07-16

  The present invention provides a novel series of indeno[1,2-c]quinolin-11-one derivatives and further provides their preparation methods as well as applications. Said applications includes utilizing such derivatives as pharmaceutical compositions for treating cancers; moreover, said applications includes the capability possessed by such derivatives to effectively inhibit cancer cell growth as well as the activity of Type I topoisomerases and can be further applied for cancer treatment.

  本发明提供了一系列新颖的indeno[1,2-c]quinolin-11-one衍生物，并进一步提供其制备方法以及应用。所述应用包括将这些衍生物用作治疗癌症的药物组合物；此外，所述应用包括这些衍生物具有有效抑制癌细胞生长以及抑制Ⅰ型拓扑异构酶活性的能力，并可进一步应用于癌症治疗。