N-[2-(3,4-二甲氧基苯基)-1-甲基乙基]-2-羟基-2-苯基乙胺 | 62717-86-6

• 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: N-[2-(3,4-二甲氧基苯基)-1-甲基乙基]-2-羟基-2-苯基乙胺
• 英文名称: N-[2-(3,4-dimethoxyphenyl)-1-methylethyl]-2-hydroxy-2-phenylethylamine
• 英文别名: 2-[1-(3,4-dimethoxyphenyl)propan-2-ylamino]-1-phenylethanol
• CAS: 62717-86-6
• 化学式: C₁₉H₂₅NO₃
• 分子量: 315.412
• InChiKey: UCZSRKKLRUJLBG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  23
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  50.7
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-[2-(3,4-二甲氧基苯基)-1-甲基乙基]-2-羟基-2-苯基乙胺 在 甲烷磺酸 作用下， 反应 2.0h， 以79%的产率得到7,8-Dimethoxy-4-methyl-1-phenyl-2,3,4,5-tetrahydro-1H-benzo[d]azepine
  参考文献：
  名称：

  Two General Routes to 1,4-Disubstituted-2,3,4,5-tetrahydro- 1H-3-benzazepines

  摘要：

  [GRAPHICS]Two general routes to 1,4disubstituted-2,3,4,5-tetrahydro-1H-3-benzazepines are described. Both routes utilize an appropriately functionalized phenethylamino alcohol as the penultimate intermediate: the first route makes use of the reductive amination of a benzyl alkyl ketone with alpha-(aminomethyl)benzyl alcohol, while the second route utilizes the addition of a Grignard reagent to the oxazolidine derived from a substitued phenylacetaldehyde and alpha-(methylaminomethyl)benzyl alcohol, In all cases studied, the cis-1,4-disubstituted-2,3,4,5-tetrahydro-1H-3-benzazepine was obtained as the major product.

  DOI：

  10.1021/ol0067641
• 作为产物：
  描述：

  2-(3,4-二甲氧基苯基)-N-甲氧基-N-甲基乙酰胺 在 sodium cyanoborohydride 、 溶剂黄146 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 15.0h， 生成 N-[2-(3,4-二甲氧基苯基)-1-甲基乙基]-2-羟基-2-苯基乙胺
  参考文献：
  名称：

  Two General Routes to 1,4-Disubstituted-2,3,4,5-tetrahydro- 1H-3-benzazepines

  摘要：

  [GRAPHICS]Two general routes to 1,4disubstituted-2,3,4,5-tetrahydro-1H-3-benzazepines are described. Both routes utilize an appropriately functionalized phenethylamino alcohol as the penultimate intermediate: the first route makes use of the reductive amination of a benzyl alkyl ketone with alpha-(aminomethyl)benzyl alcohol, while the second route utilizes the addition of a Grignard reagent to the oxazolidine derived from a substitued phenylacetaldehyde and alpha-(methylaminomethyl)benzyl alcohol, In all cases studied, the cis-1,4-disubstituted-2,3,4,5-tetrahydro-1H-3-benzazepine was obtained as the major product.

  DOI：

  10.1021/ol0067641

文献信息

• Pharmaceutical compositions and methods involving benzazepine derivatives
  申请人：SmithKline Corporation

  公开号：US04011319A1

  公开（公告）日：1977-03-08

  Pharmaceutical compositions and a method of stimulating peripheral dopamine receptors by administering internally a nontoxic effective quantity of a benzazepine derivative to an animal. Renal vasodilator and diuretic methods are also disclosed.

  药用组合物及通过向动物体内施用非毒性有效量的苯并氮杂卓衍生物来刺激外周多巴胺受体的方法。还公开了肾血管扩张剂和利尿剂的方法。
• US4011319A
  申请人：——

  公开号：US4011319A

  公开（公告）日：1977-03-08
• US5468865A
  申请人：——

  公开号：US5468865A

  公开（公告）日：1995-11-21
• [EN] STEREOPREFERENTIAL SYNTHESIS OF 3-(1-PHENYLPROP-2-YL)-5-PHENYLOXAZOLIDINONES<br/>[FR] SYNTHESE STEREOPREFERENTIELLE DU 3-(1-PHENYLPROP-2-YL)-5-PHENYLOXAZOLIDINONES
  申请人：CELGENE CORPORATION

  公开号：WO1995029903A1

  公开（公告）日：1995-11-09

  (EN) The (R,R)-diastereoisomer of oxazolidin-2-ones, which are chemical intermediates for the preparation therapeutic agents useful in the treatment of diabetes and hyperglycemia, are prepared substantially free of isomeric forms through reduction of an acid addition salt of an (R)-N-protected-N-phenylcarboxymethyl-1-phenylprop-2-ylamine to form a secondary alcohol of predominantly the (R,R) chiral form in preference to others, removal of the protecting group to form a secondary amine, and allowing the secondary amine to react with a source of carbonyl groups. A typical embodiment involves the preparation of (R,R)-3-[1-(3,4-dimethoxyphenyl)prop-2-yl]-5-(3-chlorophenyl)oxazolidin-2-one in which both the chemical purity and optical purity are in excess of 99 % .(FR) L'invention porte sur des (R, R)-diastéréoisomères d'oxazolidin-2-ones, intermédiaires de synthèse dans la préparation d'agents curatifs utilisables pour le traitement du diabète et de l'hyperglycémie et qu'on obtient pratiquement exempts de formes isomères: en réduisant un sel d'addition d'une (R)-N-phénylcarboxyméthyl-1phénylprop-2-ylamine à N protégé ce qui donne un alcool secondaire présentant une portion prépondérante de la forme (R, R) chirale de préférence aux autres, puis en en extrayant le groupe protecteur pour former une amine secondaire, puis en faisant réagir ladite amine avec une source de groupes carbonyle. L'une des applications types de l'invention porte sur la préparation de (R;R)-3-[1-3,4-diméthoxyphényl) prop-2-yl]-5-(3-chlorophényl) oxazolidin-2-one dont la pureté chimique et la pureté optique dépassent toutes deux 99 %.
• Two General Routes to 1,4-Disubstituted-2,3,4,5-tetrahydro- 1<i>H</i>-3-benzazepines
  作者：Samuel W. Gerritz、Jennifer S. Smith、Suganthini S. Nanthakumar、David E. Uehling、Jeffery E. Cobb

  DOI：10.1021/ol0067641

  日期：2000.12.1

  [GRAPHICS]Two general routes to 1,4disubstituted-2,3,4,5-tetrahydro-1H-3-benzazepines are described. Both routes utilize an appropriately functionalized phenethylamino alcohol as the penultimate intermediate: the first route makes use of the reductive amination of a benzyl alkyl ketone with alpha-(aminomethyl)benzyl alcohol, while the second route utilizes the addition of a Grignard reagent to the oxazolidine derived from a substitued phenylacetaldehyde and alpha-(methylaminomethyl)benzyl alcohol, In all cases studied, the cis-1,4-disubstituted-2,3,4,5-tetrahydro-1H-3-benzazepine was obtained as the major product.