3,4-dimethyl-N-(4-(trifluoromethyl)phenethyl)aniline | 1111734-75-8

• 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: 3,4-dimethyl-N-(4-(trifluoromethyl)phenethyl)aniline
• 英文别名: (3,4-dimethyl-phenyl)-[2-(4-trifluoromethyl-phenyl)-ethyl]-amine；3,4-dimethyl-N-[2-[4-(trifluoromethyl)phenyl]ethyl]aniline
• CAS: 1111734-75-8
• 化学式: C₁₇H₁₈F₃N
• 分子量: 293.332
• InChiKey: KQIKORPYXGAMGV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3,4-dimethyl-N-(4-(trifluoromethyl)phenethyl)aniline 、 草酰氯单乙酯 在 三乙胺 作用下， 以 乙醚 为溶剂， 反应 24.33h， 以97%的产率得到N-(3,4-dimethyl-phenyl)-N-[2-(4-trifluoromethyl-phenyl)-ethyl]-oxalamic acid ethyl ester
  参考文献：
  名称：

  MONOAMIDE DERIVATIVES AS OREXIN RECEPTOR ANTAGONISTS

  摘要：

  本发明涉及以下式的化合物 其中 Ar，R 1 ，R 2 ，R 3 ，R 4 ，R 5 ，n，o和p如本文所定义 或其药用合适的酸盐、光学纯对映体、拉氏体或二对映异构体混合物。式I的化合物可用于治疗睡眠障碍，如睡眠呼吸暂停症、嗜睡症、失眠、睡眠障碍、时差综合征、昼夜节律紊乱或与神经系统疾病相关的睡眠障碍。

  公开号：

  US20090036422A1
• 作为产物：
  描述：

  N-(3,4-dimethylphenyl)-2-(4-(trifluoromethyl)phenyl)acetamide 在 硼烷四氢呋喃络合物 、 盐酸 、 水 作用下， 以 四氢呋喃 为溶剂， 反应 21.0h， 生成 3,4-dimethyl-N-(4-(trifluoromethyl)phenethyl)aniline
  参考文献：
  名称：

  MONOAMIDE DERIVATIVES AS OREXIN RECEPTOR ANTAGONISTS

  摘要：

  本发明涉及以下式的化合物 其中 Ar，R 1 ，R 2 ，R 3 ，R 4 ，R 5 ，n，o和p如本文所定义 或其药用合适的酸盐、光学纯对映体、拉氏体或二对映异构体混合物。式I的化合物可用于治疗睡眠障碍，如睡眠呼吸暂停症、嗜睡症、失眠、睡眠障碍、时差综合征、昼夜节律紊乱或与神经系统疾病相关的睡眠障碍。

  公开号：

  US20090036422A1

文献信息

• Copper-Catalyzed Aerobic Oxidative Cross-Dehydrogenative Coupling of Amine and α-Carbonyl Aldehyde: A Practical and Efficient Approach to α-Ketoamides with Wide Substrate Scope
  作者：Chun Zhang、Xiaolin Zong、Liangren Zhang、Ning Jiao

  DOI：10.1021/ol301130u

  日期：2012.7.6

  A copper-catalyzed aerobic oxidative cross-dehydrogenative coupling (CDC) of amine with α-carbonyl aldehyde has been developed. Many types of amines are tolerant in this transformation leading to various α-ketoamides compounds. Wide substrate scope, CDC strategy and using air as oxidant make this transformation highly efficient and practical. Molecular oxygen acts not only as the oxidant, but also

  已经开发了铜与胺的α-羰基醛的铜催化的需氧氧化交叉脱氢偶联（CDC）。许多类型的胺可耐受这种转化，从而导致产生各种α-酮酰胺化合物。广泛的底物范围，CDC策略以及使用空气作为氧化剂，使这种转化高效而实用。分子氧不仅充当氧化剂，还充当引发该催化过程的引发剂。此外，机理研究表明，α-羰基醛的羰基起着促进该化学过程的指导基团的作用。
• Copper-Catalyzed Aerobic Oxidative Coupling of Aryl Acetaldehydes with Anilines Leading to α-Ketoamides
  作者：Chun Zhang、Zejun Xu、Liangren Zhang、Ning Jiao

  DOI：10.1002/anie.201105285

  日期：2011.11.18

  reaction provides an efficient route to α‐ketoamides compounds, which are ubiquitous structural units in a number of biologically active compounds. N‐substituted anilines are suitable substrates for this transformation. Two CH bonds as well as one CH and one NH bond are cleaved in this reaction. Molecular oxygen (1 atm) is used as the oxidant and the reaction involves dioxygen activation.

  高效实用：标题反应为α-酮酰胺化合物提供了一条有效途径，α-酮酰胺化合物是许多生物活性化合物中普遍存在的结构单元。N-取代的苯胺是该转化的合适底物。两个C  H键以及一种C  H和一个N-  H键被裂解在该反应中。分子氧（1个大气压）用作氧化剂，反应涉及双氧活化。
• Copper-Catalyzed Synthesis of α-Keto Amides from Sulfoxonium Ylides
  作者：Xinghua Wang、Yazhou Li、Naixuan Zhao、Hong Liu、Yu Zhou

  DOI：10.1021/acs.joc.3c00281

  日期：2023.7.7

  We here described a method to synthesize α-keto amides from simple sulfoxonium ylides and secondary amines under the catalysis of copper. This transformation involved a very simple and clean catalytic system, and the substrates could be extended to aryl, heteroaryl, and tert-butyl sulfoxonium ylides to give diversified α-keto amides with good yields. Additionally, the mechanistic studies indicated

  我们在这里描述了一种在铜催化下由简单的亚砜叶立德和仲胺合成α-酮酰胺的方法。该转化涉及非常简单和清洁的催化体系，并且底物可以扩展到芳基、杂芳基和叔丁基亚锍叶立德，从而以良好的收率得到多样化的α-酮酰胺。此外，机理研究表明α-羰基醛可能是反应体系中的关键中间体。
• [EN] MONOAMIDE DERIVATIVES AS OREXIN RECEPTOR ANTAGONISTS<br/>[FR] DÉRIVÉS MONOAMIDE EN TANT QU'ANTAGONISTES DE RÉCEPTEURS AUX ORÉXINES
  申请人：HOFFMANN LA ROCHE

  公开号：WO2009016087A1

  公开（公告）日：2009-02-05

  The present invention relates to compounds of formula (I), wherein Ar is aryl or heteroaryl; R1 is hydrogen, halogen, lower alkyl, lower alkyl substituted by halogen, lower alkoxy, lower alkoxy substituted by halogen, cyano, SO2-lower alkyl or hydroxy; R2 is hydrogen, halogen, lower alkyl, lower alkyl substituted by halogen, lower alkoxy, lower alkoxy substituted by halogen, cyano, S-lower alkyl, SO2-lower alkyl, NO2 or hydroxy; R3 is hydrogen, halogen, lower alkyl, lower alkyl substituted by halogen, lower alkoxy, -(CH2)m-O-lower alkyl, lower alkoxy substituted by halogen, 3-hydroxy-oxetan-3-yl, cyano or SO2-lower alkyl; or if o is 2, R3 may form in 3 and 4 position together with the carbon atoms to which they are attached an addional ring with the groups -O-CH2-O-, -O-CF2-CF2-O-, -N=CH-S-, -O-CF2-O-, -(CH2)4-, -NH-C(O)-NH-, -O-(CH2)2- or _(CH2)2-O-; R4/R5 are independently from each other hydrogen, -(CR'2)mOH, lower alkyl, lower alkoxy, -NRR', or is -(CH2)0,1-heterocycloalkyl, optionally substituted by hydroxy, or R4 and R5 are together =O or =N-OH,; R/R' are independently from each other hydrogen, lower alkyl, C(O)H, -(CR'2)m-OH, -(CR'2)m-NR'2, -(CR'2)m-NR'-C(O)-lower alkyl, -(CR'2)m-O-lower alkyl, -(CR'2)m-O-lower alkenyl, -C(O)O-lower alkyl, -C(O)-CR'2-NH-C(O)O-lower alkyl, -C(O)-CR'2-NR'2, or is -(CH2)0,1-heterocycloalkyl or -(CH2)0,1-furan-2-yl; R' are independently from each other hydrogen, lower alkoxy, phenyl or lower alkyl; n is 1, 2, 3 or 4; o is 1, 2 or 3; p is 1, 2 or 3; m is 1, 2 or 3; or to pharmaceutically suitable acid addition salts, optically pure enantiomers, racemates or diastereomeric mixtures thereof. The compounds of formula (I) may be used for example for the treatment of the sleep disorders, which are sleep apnea, narcolepsy, insomnia, parasomnia, jet lag syndrome, circadian rhythms disorder or sleep disorders associated with neurological diseases.
• MONOAMIDE DERIVATIVES AS OREXIN RECEPTOR ANTAGONISTS
  申请人：Knust Henner

  公开号：US20090036422A1

  公开（公告）日：2009-02-05

  The present invention relates to compounds of formula wherein Ar, R 1 , R 2 , R 3 , R 4 , R 5 , n, o, and p are as defined herein or to pharmaceutically suitable acid addition salts, optically pure enantiomers, racemates or diastereomeric mixtures thereof. The compounds of formula I can be used for the treatment of sleep disorders, such as sleep apnea, narcolepsy, insomnia, parasomnia, jet lag syndrome, circadian rhythms disorder or sleep disorders associated with neurological diseases.

  本发明涉及以下式的化合物 其中 Ar，R 1 ，R 2 ，R 3 ，R 4 ，R 5 ，n，o和p如本文所定义 或其药用合适的酸盐、光学纯对映体、拉氏体或二对映异构体混合物。式I的化合物可用于治疗睡眠障碍，如睡眠呼吸暂停症、嗜睡症、失眠、睡眠障碍、时差综合征、昼夜节律紊乱或与神经系统疾病相关的睡眠障碍。