2-phenyl-1-(3,4-dimethoxyphenyl)ethyl amine | 80235-75-2

• 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: 2-phenyl-1-(3,4-dimethoxyphenyl)ethyl amine
• 英文别名: 3,4-dimethoxy-bibenzyl-α-ylamine；3,4-Dimethoxy-bibenzyl-α-ylamin；α-(3,4-dimethoxyphenyl)-β-phenylethylamine；α-(3,4-dimethoxyphenyl)benzeneethanamine；α-(3.4-dimethoxyphenyl)benzeneethanamine；1-(3,4-dimethoxyphenyl)-2-phenylethylamine；alpha-(3,4-Dimethoxyphenyl)benzeneethanamine；1-(3,4-dimethoxyphenyl)-2-phenylethanamine
• CAS: 80235-75-2
• 化学式: C₁₆H₁₉NO₂
• 分子量: 257.332
• InChiKey: WAKRXOCPJKLWAS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  44.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-phenyl-1-(3,4-dimethoxyphenyl)ethyl amine 在 氢溴酸 作用下， 生成 α-amino-bibenzyl-3,4-diol
  参考文献：
  名称：

  Nerlekar; Nargund, Journal of the Karnatak University, 1957, vol. 2, p. 66

  摘要：

  DOI：
• 作为产物：
  描述：

  3’,4’-二甲氧基苯基苯乙酮 在 盐酸 作用下， 生成 2-phenyl-1-(3,4-dimethoxyphenyl)ethyl amine
  参考文献：
  名称：

  Nerlekar; Nargund, Journal of the Karnatak University, 1957, vol. 2, p. 66

  摘要：

  DOI：

文献信息

• Selective .beta..sub.3 agonists for the treatment of diabetes and obesity
  申请人：Merck & Co., Inc.

  公开号：US05714506A1

  公开（公告）日：1998-02-03

  Compounds of formula ##STR1## are selective .beta..sub.3 adrenergic receptor agonists with very little .beta..sub.1 and .beta..sub.2 adrenergic receptor activity and as such the compounds are capable of increasing lipolysis and energy expenditure in cells. The compounds thus have potent activity in the treatment of Type II diabetes and obesity. The compounds can also be used to lower triglyceride levels and cholesterol levels or raise high density lipoprotein levels or to decrease gut motility. In addition, the compounds can be used to reduced neurogenic inflammation or as antidepressant agents.

  公式为##STR1##的化合物是选择性的β3肾上腺素受体激动剂，几乎没有β1和β2肾上腺素受体活性，因此这些化合物能够增加细胞内的脂解和能量消耗。因此，这些化合物在治疗2型糖尿病和肥胖症方面具有强效活性。这些化合物还可以用于降低甘油三酯水平和胆固醇水平，或提高高密度脂蛋白水平，或减少肠道蠕动。此外，这些化合物还可以用于减少神经源性炎症或作为抗抑郁药物。
• Rapid, one-pot synthesis of α,α-disubstituted primary amines by the addition of Grignard reagents to nitriles under microwave heating conditions
  作者：Brian T. Gregg、Kathryn C. Golden、John F. Quinn、Hong-Jun Wang、Wei Zhang、Ruifang Wang、Francis Wekesa、Dmytro O. Tymoshenko

  DOI：10.1016/j.tetlet.2009.04.081

  日期：2009.7

  A series of α,α-disubstituted amines have been prepared in a simple and efficient one-pot procedure by the addition of Grignard reagents to a series of aliphatic, aromatic, and heteroaromatic nitriles. Key to this reported procedure is the unprecedented addition of the Grignard reagent to the nitrile under heating by microwave irradiation which both significantly improves reaction yields and reduces

  通过将格氏试剂添加到一系列脂族，芳族和杂芳族腈中，以简单有效的一锅法制备了一系列α，α-二取代胺。该报道方法的关键是在微波辐射加热下，将格氏试剂前所未有地添加到腈中，这既显着提高了反应产率，又缩短了反应时间。通常，格利雅（Grignard）加成反应在100°C下5-10分钟内完成，然后用硼氢化钠快速还原，得到目标胺。
• Aryloxypropanolamine .beta. 3 adrenergic agonists
  申请人：Bristol-Myers Squibb Company

  公开号：US05541204A1

  公开（公告）日：1996-07-30

  Compounds of the formula ##STR1## and pharmaceutically acceptable salts thereof wherein: R.sup.1 to R.sup.9 are as defined herein and m is the integer 0 or 1. These compounds are beta 3 adrenergic receptor agonists and are useful, therefore for example, in the treatment of diabetes, obesity, gastrointestinal diseases and achalasia.

  化合物的公式为##STR1##及其药学上可接受的盐，其中：R.sup.1至R.sup.9如此处所定义，m为整数0或1。这些化合物是β3肾上腺素能受体激动剂，因此例如在糖尿病、肥胖症、胃肠道疾病和食管失弛缓症的治疗中有用。
• Catecholamine surrogates useful as .beta..sub.3 agonists
  申请人：Bristol-Myers Squibb Company

  公开号：US05776983A1

  公开（公告）日：1998-07-07

  Compounds of the formula ##STR1## or pharmaceutically acceptable salts thereof wherein: A is a bond, --(CH.sub.2).sub.n -- or --CH(B)--, where n is an integer of 1 to 3 and B is --CN, --CON(R.sup.9)R.sup.9' or --CO.sub.2 R.sup.7 ; R.sup.1 is lower alkyl, aryl or arylalkyl; R.sup.2 is hydrogen, hydroxy, alkoxy, --CH.sub.2 OH, cyano, --C(O)OR.sup.7, --CO.sub.2 H, --CONH.sub.2, tetrazole, --CH.sub.2 NH.sub.2 or halogen; ##STR2## R.sup.3 is hydrogen, alkyl, heterocycle or R.sup.4 is hydrogen, alkyl or B; R.sup.5, R.sup.5', R.sup.8, R.sup.8' or R.sup.8" are independently hydrogen, alkoxy, lower alkyl, halogen, --OH, --CN, --(CH.sub.2).sub.n NR.sup.6 COR.sup.7, --CON(R.sup.6)R.sup.6', --CON(R.sup.6)OR.sup.6', --CO.sub.2 R.sup.6, --SR.sup.7, --SOR.sup.7, --SO.sub.2 R.sup.7, --N(R.sup.6)SO.sub.2 R.sup.1, --N(R.sup.6)R.sup.6', --NR.sup.6 COR.sup.7, --OCH.sub.2 CON(R.sup.6)R.sup.6', --OCH.sub.2 CO.sub.2 R.sup.7 or aryl; or R.sup.5 and R.sup.5' or R.sup.8 and R.sup.8' may together with the carbon atoms to which they are attached form an aryl or heterocycle; R.sup.6 and R.sup.6' are independently hydrogen or lower alkyl; and R.sup.7 is lower alkyl; R.sup.9 is hydrogen, lower alkyl, alkyl, cycloalkyl, arylalkyl, aryl, heteroaryl; or R.sup.9 and R.sup.9' may together with the nitrogen atom to which they are attached form a heterocycle; with the proviso that when A is a bond or --(CH.sub.2).sub.n and R.sup.3 is hydrogen or unsubstituted alkyl, then R.sup.4 is B or substituted alkyl. These compounds are beta.sub.3 adrenergic receptor agonists and are useful, therefore for example, in the treatment of diabetes, obesity and gastrointestinal diseases.

  化合物的结构式为##STR1##或其药学上可接受的盐，其中：A是一个键，--(CH.sub.2).sub.n--或--CH(B)--，其中n是1到3的整数，B是--CN，--CON(R.sup.9)R.sup.9'或--CO.sub.2R.sup.7; R.sup.1是低碳基，芳香基或芳基烷基; R.sup.2是氢，羟基，烷氧基，--CH.sub.2OH，氰基，--C(O)OR.sup.7，--CO.sub.2H，--CONH.sub.2，四唑，--CH.sub.2NH.sub.2或卤素; ##STR2## R.sup.3是氢，烷基，杂环或R.sup.4是氢，烷基或B; R.sup.5，R.sup.5'，R.sup.8，R.sup.8'或R.sup.8"独立地是氢，烷氧基，低碳基，卤素，--OH，--CN，--(CH.sub.2).sub.nNR.sup.6COR.sup.7，--CON(R.sup.6)R.sup.6'，--CON(R.sup.6)OR.sup.6'，--CO.sub.2R.sup.6，--SR.sup.7，--SOR.sup.7，--SO.sub.2R.sup.7，--N(R.sup.6)SO.sub.2R.sup.1，--N(R.sup.6)R.sup.6'，--NR.sup.6COR.sup.7，--OCH.sub.2CON(R.sup.6)R.sup.6'，--OCH.sub.2CO.sub.2R.sup.7或芳香基; 或R.sup.5和R.sup.5'或R.sup.8和R.sup.8'可以与它们连接的碳原子一起形成一个芳香基或杂环; R.sup.6和R.sup.6'独立地是氢或低碳基; R.sup.7是低碳基; R.sup.9是氢，低碳基，烷基，环烷基，芳基烷基，芳香基，杂芳基; 或R.sup.9和R.sup.9'可以与它们连接的氮原子一起形成一个杂环; 假设当A是键或--(CH.sub.2).sub.n时，R.sup.3是氢或未取代的烷基，则R.sup.4是B或取代的烷基。这些化合物是beta.sub.3肾上腺素受体激动剂，因此在糖尿病，肥胖症和胃肠疾病的治疗中有用。
• Synthesis of amines
  申请人：SUMITOMO CHEMICAL COMPANY, LIMITED

  公开号：EP0008532A1

  公开（公告）日：1980-03-05

  A process for the preparation of an amide of the formula wherein R is an eventually substituted alkyl, alkenyl, aralkyl or phenyl group, by hydrolysis of a nitrile of the formula (II) wherein R is as defined above, in the presence of a base and hydrogen peroxide using an organic quaternary ammonium salt and/or a tertiary amine as a catalyst. This process is useful for the preparation of amides of formula (III) wherein n is 1, 2 or 3 Ar and Ar' are eventually substituted phenyl groups R3 is hydrogen or a substituent. These amides can be decomposed in amines by a halogen or a hypohalite in the presence of a base.

  一种通过水解式（II）腈制备式（I）酰胺的工艺 其中 R 是最终取代的烷基、烯基、芳基或苯基，通过水解式（II）的腈 其中 R 如上定义，在碱和过氧化氢存在下，使用有机季铵盐和/或叔胺作为催化剂。该工艺可用于制备式 (III) 的酰胺 其中 n 为 1、2 或 3 Ar 和 Ar'为最终取代的苯基 R3 是氢或取代基。 这些酰胺可以在碱存在下通过卤素或次卤素分解成胺。