五甲苯胺 | 2243-30-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 五甲苯胺
• 英文名称: pentamethylaniline
• 英文别名: 2,3,4,5,6-pentamethylaniline
• CAS: 2243-30-3
• 化学式: C₁₁H₁₇N
• 分子量: 163.263
• InChiKey: DCBKKCYNUSINPI-UHFFFAOYSA-N

物化性质

• 熔点：
  152.5°C
• 沸点：
  253.03°C (estimate)
• 密度：
  0.9137 (estimate)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  26
• 氢给体数：
  1
• 氢受体数：
  1

安全信息

• 海关编码：
  2921430090

反应信息

• 作为反应物：
  描述：

  五甲苯胺 在 盐酸 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 17.0h， 生成 N-(4-chloro-3-methyl-5-isoxazolyl)-2-(pentamethylphenylaminocarbonyl)thiophene-3-sulfonamide
  参考文献：
  名称：

  Endothelin Antagonists:  Substituted Mesitylcarboxamides with High Potency and Selectivity for ET_A Receptors

  摘要：

  We have previously disclosed the discovery of 2,4-disubstituted anilinothiophenesulfonamides with potent ETA-selective endothelin receptor antagonism and the subsequent identification of sitaxsentan (TBC11251, 1) as a clinical development compound (Wu et al. J. Med. Chem. 1997, 40, 1682 and 1690). The orally active 1 has demonstrated efficacy in a phase II clinical trial of congestive heart failure (Givertz ct al. Circulation 1998, 98, Abstr. #3044) and was active in rat models of myocardial infarction (Podesser et al. Circulation. 1998, 98, Abstr. #2896) and acute hypoxia-induced pulmonary hypertension (Chen et al. FASEB J. 1996, 10 (3), A104). We now report that an additional substituent at the 6-position of the anilino ring further increases the potency of this series of compounds. It was also found that a wide range of functionalities at the 3-position of the 2,4,6-trisubstituted ring increased ETA selectivity by similar to 10-fold while maintaining in vitro potency, therefore rendering the compounds amenable to fine-tuning of pharmacological and toxicological profiles with enhanced selectivity. The optimal compound in this series was found to be TBC2576 (7u), which has similar to 10-fold higher ETA binding affinity than 1, high ETA/ETB selectivity, and a serum half-life of 7.3 h in rats, as well as in vivo activity.

  DOI：

  10.1021/jm9900063
• 作为产物：
  描述：

  五甲基苯 在 N-BOC-O-甲苯磺酰羟胺 作用下， 反应 240.0h， 以27%的产率得到五甲苯胺
  参考文献：
  名称：

  无金属直接芳烃 C−H 胺化

  摘要：

  通过形成 CN 键合成芳胺是制备功能材料、活性药物成分和生物活性产品的重要工具。通常，这种化学连接只能通过过渡金属催化的反应、光化学或电化学来实现。在这里，我们报告了在良性条件下使用羟胺衍生物进行的无金属芳烃 C-H 胺化。即使在存在各种官能团的情况下，胺化试剂 TsONHR 和芳烃底物之间的电荷转移相互作用也能实现芳烃的化学选择性胺化。氧气对于有效转化至关重要，其对电子转移步骤的加速作用已通过实验证明。此外，

  DOI：

  10.1002/adsc.202100236

文献信息

• Anti-Viral Compounds
  申请人：DeGoey David A.

  公开号：US20100317568A1

  公开（公告）日：2010-12-16

  Compounds effective in inhibiting replication of Hepatitis C virus (“HCV”) are described. This invention also relates to processes of making such compounds, compositions comprising such compounds, and methods of using such compounds to treat HCV infection.

  描述了一种有效抑制丙型肝炎病毒（“HCV”）复制的化合物。本发明还涉及制备这种化合物的方法、包含这种化合物的组合物，以及使用这种化合物治疗HCV感染的方法。
• Synthesis of Quaternary Carbon Stereocenters by Copper-Catalyzed Asymmetric Allylic Substitution of Allyl Phosphates with Arylboronates
  作者：Momotaro Takeda、Keishi Takatsu、Ryo Shintani、Tamio Hayashi

  DOI：10.1021/jo500068p

  日期：2014.3.21

  A copper-catalyzed asymmetric allylic substitution of γ,γ-disubstituted allyl phosphates with arylboronates has been developed for the construction of quaternary stereocenters. High regio- and enantioselectivities have been achieved by employing a hydroxy-bearing chiral N-heterocyclic carbene ligand, and both E and Z substrates provide the same enantiomer as the major product. The mechanistic aspect

  已经开发了用芳基硼酸酯的铜催化的γ，γ-二取代的烯丙基磷酸的不对称烯丙基取代基，用于构建季立体中心。通过使用带有羟基的手性N-杂环卡宾配体已经实现了高区域选择性和对映体选择性，并且E和Z底物均提供与主要产物相同的对映异构体。还已经研究了这种催化作用的机理，以发现1：1的铜/配体络合物最有可能导致当前的不对称催化作用，并且相对于烯丙基亲电试剂，反应以几乎完美的1,3-抗立体化学进行。
• N-heteroaryl aryl-substituted thienyl-furyl-and pyrrolyl-sulfonamides and derviatives thereof that modulate the activity of endothelin
  申请人：Texas Biotechnology Corporation

  公开号：US06420567B1

  公开（公告）日：2002-07-16

  Thienyl-, furyl- and pyrrolyl-sulfonamides, formulations of pharmaceutically-acceptable salts thereof and methods for modulating or altering the activity of the endothelin family of peptides are provided. In particular, N-(isoxazolyl)thienylsulfonamides, N-(isoxazolyl)furylsulfonamides and N-(isoxazolyl)pyrrolylsulfonamides, formulations thereof and methods using these sulfonamides for inhibiting the binding of an endothelin peptide to an endothelin receptor by contacting the receptor with the sulfonamide are provided. Methods for treating endothelin-mediated disorders by administering effective amounts of one or more of these sulfonamides or prodrugs thereof that inhibit the activity of endothelin are also provided.

  噻吩基、呋喃基和吡咯基磺酰胺，以及它们的药物可接受盐的配方，以及调节或改变内皮素肽家族活性的方法。特别是，提供N-(异恶唑基)噻吩磺酰胺、N-(异恶唑基)呋喃磺酰胺和N-(异恶唑基)吡咯磺酰胺，它们的配方以及使用这些磺酰胺通过将受体与磺酰胺接触来抑制内皮素肽与内皮素受体结合的方法。还提供了通过给予有效量的一个或多个这些磺酰胺或抑制内皮素活性的前药来治疗内皮素介导的疾病的方法。
• Acid-Catalyzed [3,3]-Sigmatropic Rearrangements ofN-Propargylanilines
  作者：Peter Barmettler、Hans-J�rgen Hansen

  DOI：10.1002/hlca.19900730602

  日期：1990.9.19

  optical activity of the starting aniline was observed in the acid-catalyzed rearrangement of (−)-(S)-2,6-dimethyl-N-[1′-(p-tolyl)prop-2′-ynyl]aniline ((−)-42; cf. Scheme 25). N-[1′-(p-anisyl)prop-2-ynyl]-2,4,6-trimethylaniline(43; cf. Scheme 25) underwent no acid-catalyzed [3,3]-sigmatropic rearrangement at all. The acid-catalyzed rearrangement of N-(1′,1′-dimethylprop-2′-ynyl)aniline (25; cf. Scheme 10)

  N-（1'，1'-二甲基丙-2'-炔基）-，N-（1'-甲基丙-2'-炔基）-和N-（1'-芳基丙-2'的酸催化重排-Nyn）-2,6-，2,4,6-，2,3,5,6-和2,3,4,5,6-取代的苯胺在1N H 2 SO 4水溶液和ROH的混合物中例如EtOH，PrOH，BuOH等，或在CDCl 3或CCl 4中，在4至9摩尔当量的存在下。三氟乙酸（TFA）进行了研究（参见方案12 - 25和表6和7）。CDCl中N-（3'-X-1'，1'-二甲基-丙-2'-炔基）-2,6-和2,4,6-三甲基苯胺（X = Cl，Br，I）的重排3/ TFA在20℃已经发生与τ 1/2 CA的 1至5小时得到相应的6-（1-X-3'-甲基丁基-1,2'-二烯基）-2,6-二甲基-或2,4,6-三甲基环己-2,4-二烯-1 -亚胺离子（参见方案13和脚注26和34）当4位未被取代时，会发生连续的[3,3]-σ重排，从而生成2
• Regular Two-Dimensional Arrays of Surface-Mounted Molecular Switches: Switching Monitored by UV–vis and NMR Spectroscopy
  作者：Carina Santos Hurtado、Guillaume Bastien、Milan Mašát、Jakub Radek Štoček、Martin Dračínský、Igor Rončević、Ivana Císařová、Charles T. Rogers、Jiří Kaleta

  DOI：10.1021/jacs.0c01753

  日期：2020.5.20

  Using solid-state 15N NMR spectroscopy, the cis/trans isomerization in a 2-D array of surface-mounted azobenzene-based switches was detected for the first time. In order to achieve this, a new class of rod-shaped molecular switches, suitable for formation of two-dimensional regular arrays on large facets of tris(o-phenylenedioxy)cyclotriphosphazene (TPP) nanocrystals, was synthesized. A mechanochemical

  使用固态 15N NMR 光谱，首次检测到表面安装的偶氮苯开关二维阵列中的顺/反异构化。为了实现这一点，合成了一类新的棒状分子开关，适用于在三（邻苯二氧基）环三磷腈（TPP）纳米晶体的大平面上形成二维规则阵列。机械化学方法用于在 TPP 基质中制备相应的主客体表面夹杂物。溶液中的热步骤和超分子表面夹杂物的比较表明，单个分子的转换不受相邻分子的影响。