1-(2-Phenylethyl)-1-phenylhydrazine | 65249-04-9

• 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: 1-(2-Phenylethyl)-1-phenylhydrazine
• 英文别名: N-amino-N-phenethylaniline；N-phenethyl-N-phenyl-hydrazine；N-Phenaethyl-N-phenyl-hydrazin；N-Phenyl-N-phenethyl-hydrazin；Hydrazine, 1-phenyl-1-(2-phenylethyl)-；1-phenyl-1-(2-phenylethyl)hydrazine
• CAS: 65249-04-9
• 化学式: C₁₄H₁₆N₂
• 分子量: 212.294
• InChiKey: AORSMXGTRACRRH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  29.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(2-Phenylethyl)-1-phenylhydrazine 在 2-丁烯腈 、 palladium 10% on activated carbon 、 zinc(II) chloride 作用下， 以 2-甲基-2-丁醇 、 甲苯 为溶剂， 反应 15.0h， 生成 3-methyl-1-phenethyl-1H-indole
  参考文献：
  名称：

  钯催化的胺类脱氢生成胺。通过胺与芳肼的交叉偶联反应获得吲哚的自然路线

  摘要：

  AbstractH‐substituted imines are elusive compounds formed when aldehydes or ketones are mixed with ammonia. However, this class of molecules can be prepared through selective removal of a hydrogen molecule from a primary amine using a transition metal catalyst. This biomimetic transformation, previously employed for the N‐alkylation of anilines, is applied here to a domino preparation of differently substituted indoles from aliphatic primary amines and arylhydrazines. Several different linear and branched aliphatic primary amines are oxidized with reusable palladium on charcoal to the corresponding primary imines entrapped as arylhydrazones that can be isolated as such. Arylhydrazones can be further converted into N‐alkylindole derivatives via an acid‐mediated indolisation reaction. The one‐pot domino hydrogen transfer Fischer indole synthesis under heterogeneous catalysis is also possible, giving access to diverse substituted indoles, including NH indoles obtained after deprotection of the corresponding benzyl compounds. The truly heterogeneous nature of the catalyst was demonstrated by recycling the catalyst in the same reaction, and in other palladium‐catalysed transformations.magnified image

  DOI：

  10.1002/adsc.201300559
• 作为产物：
  描述：

  2-[N-(2-phenylethyl)anilino]isoindole-1,3-dione 在 一水合肼 作用下， 以 乙醇 为溶剂， 以91%的产率得到1-(2-Phenylethyl)-1-phenylhydrazine
  参考文献：
  名称：

  A Convenient Synthesis of 1-Alkyl-1-phenylhydrazines fromN-Aminophthalimide

  摘要：

  N-Alkylaminophthalimides were synthesized by condensation of N-aminophthalimide with aldehydes, and subsequent reduction of the intermediate with pyridine-borane in acetic acid. N-Phenylation and removal of the phthalimide group gave 1-alkyl-1-phenylhydrazines in high yield.

  DOI：

  10.1081/scc-120015563

文献信息

• β-Phenylethylamines, Indolines and Isoquinolones via Hydroamination of Styrenes by Microwave Irradiation
  作者：Julio A. Seijas、M. Pilar Vázquez-Tato、M. Montserrat Martínez

  DOI：10.1055/s-2001-14585

  日期：——

  Microwave irradiation promotes hydroamination of styrenes. This method can be used as a direct way of producing different kinds of bioactive compounds: open chain compounds like β-phenylethylamines or cyclized products like indolines or isoquinolones.

  微波辐射促进了苯乙烯的胺化反应。这种方法可作为直接合成各种生物活性化合物的途径，包括开链化合物如β-苯乙胺，以及环化产物如吲哚啉或异喹啉酮。
• Potassium Hydroxide Catalyzed Addition of Arylamines to Styrenes
  作者：Sven Doye、Daniel Jaspers

  DOI：10.1055/s-0030-1260555

  日期：2011.6

  Potassium hydroxide is a competent and cheap catalyst for theintermolecular addition of arylamines to styrenes. The reactionsare performed in nontoxic dimethyl sulfoxide and can be used forthe large-scale synthesis of β-phenylethylamines.

  氢氧化钾是一种有效且廉价的催化剂，可用于芳胺与苯乙烯的分子间加成。该反应在无毒二甲亚砜中进行，可用于β-苯乙胺的大规模合成。
• Synthesis of trisubstituted hydrazine <i>via</i> MnO₂-promoted oxidative coupling of <i>N</i>,<i>N</i>-disubstituted hydrazine and boronic ester
  作者：Jiaoyang Wang、Danfeng Wang、Xiaofeng Tong

  DOI：10.1039/d1ob00929j

  日期：——

  oxidative coupling process between N,N-disubstituted hydrazine and boronic ester is reported. A 1,1-diazene species is firstly generated upon oxidation of a hydrazine substrate in the presence of MnO2 which then interacts with boronic ester to form the key intermediate boron-ate complex, followed by migration from boron to nitrogen to form a new C–N bond. This new finding provides mild, scalable, and

  报道了MnO 2促进的N，N-二取代肼和硼酸酯之间的氧化偶联过程。首先在 MnO 2存在下氧化肼底物产生 1,1-二氮烯物种，然后与硼酸酯相互作用形成关键的中间体硼酸酯复合物，然后从硼迁移到氮形成新的 C -N 键。这一新发现提供了对三取代肼的温和、可扩展且操作简单的途径。
• A trifluoromethanesulfonic acid-catalyzed reaction of arylhydrazines with benzene
  作者：Toshiharu Ohta、Shinji Miyake、Koichi Shudo

  DOI：10.1016/s0040-4039(00)98933-0

  日期：——

  Arylhydrazines reacted with benzene in the presence of trifluoromethanesulfonic acid (TFSA) to give aminobiphenyls. This is a general method for the synthesis of aminobiphenyls.

  在三氟甲磺酸（TFSA）存在下，芳肼与苯反应生成氨基联苯。这是合成氨基联苯的通用方法。
• Sufentanil and medetomidine anaesthesia in the rat and its reversal with atipamezole and butorphanol
  作者：P. Hedenqvist、J. V. Roughan、P. A. Flecknell

  DOI：10.1258/002367700780384762

  日期：2000.7.1

  Injectable anaesthetics are widely used to anaesthetize rats, but recovery times are often prolonged. Reversible anaesthetic regimens have the advantage that animals may be recovered quickly, thus reducing the incidence of postoperative complications such as hypothermia, and also providing a means of treating inadvertent anaesthetic overdose. This study assessed and compared the characteristics of anaesthesia induced with combinations of sufentanil and medetomidine administered as a single subcutaneous or intraperitoneal dose, and reversal with butorphanol and atipamezole. Combinations of sufentanil/medetomidine at 40 μg/150 μg and 50 μg/150 μg/kg administered subcutaneously, and 80 μg/300 μg/kg by intraperitoneal injection were found to produce surgical anaesthesia for 101 ± 49, 124 ± 45 and 76 ± 23 min (means ± SD) respectively. All three combinations produced marked respiratory depression 30min after injection (< 50% of resting respiratory rate). Oxygen saturation, measured by pulse oximetry, was < 50% in all groups 30 min following drug administration. Subcutaneous administration is recommended since it resulted in a more reliable and more rapid induction of anaesthesia than intraperitoneal administration. The administration of butorphanol and atipamezole (0.2/0.5 mg/kg s.c.) resulted in a rapid (< 7 min) reversal of anaesthesia and an associated respiratory depression. The induction of anaesthesia with sufentanil/medetomidine and its reversal with a combination of atipamezole and butorphanol is an effective technique for anaesthetizing rats. However, due to the marked respiratory depression and the resulting hypoxia, we recommend that this regimen should only be used in animals which are free from respiratory disease and that oxygen should be provided during anaesthesia.

  可注射的麻醉剂广泛用于麻醉大鼠，但恢复时间常常很长。可逆麻醉方案的优点是动物可以快速恢复，从而减少术后并发症（如低体温），并提供治疗意外麻醉过量的手段。本研究评估和比较了以舒芬太尼和美托咪啉组合为单一皮下或腹腔注射剂量诱导的麻醉特性，并以布托啡和阿托品为逆转剂的特性。发现皮下注射舒芬太尼/美托咪啉剂量为40μg/150μg和50μg/150μg/kg，腹腔注射舒芬太尼/美托咪啉剂量为80μg/300μg/kg，分别可产生手术麻醉，持续时间分别为101±49、124±45和76±23分钟（平均值±标准差）。所有三种组合在注射后30分钟产生明显的呼吸抑制（<休息呼吸率的50%）。脉搏血氧饱和度在所有组中注射药物后30分钟均<50％。建议采用皮下注射，因为相对于腹腔注射，皮下注射会产生更可靠和更快速的麻醉诱导。布托啡和阿托品（0.2/0.5 mg/kg皮下注射）的注射导致麻醉迅速逆转（<7分钟），并伴有呼吸抑制。使用舒芬太尼/美托咪啉诱导麻醉并使用阿托品和布托啡组合进行逆转是麻醉大鼠的有效技术。但是，由于明显的呼吸抑制和由此导致的低氧血症，我们建议仅在没有呼吸系统疾病的动物中使用此方案，并在麻醉过程中提供氧气。