(1R)-1-(1'-adamantyl)-2-bromo-1-hydroxyethane | 145238-44-4

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 卤代醇
• 英文名称: (1R)-1-(1'-adamantyl)-2-bromo-1-hydroxyethane
• 英文别名: (1R)-1-(1-adamantyl)-2-bromoethanol
• CAS: 145238-44-4
• 化学式: C₁₂H₁₉BrO
• 分子量: 259.186
• InChiKey: JOPAFDSOJPEXPK-CRCJWISWSA-N

物化性质

• 沸点：
  330.9±15.0 °C(Predicted)
• 密度：
  1.435±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (1R)-1-(1'-adamantyl)-2-bromo-1-hydroxyethane 在 盐酸 、 sodium hydroxide 、 正丁基锂 、 三氟甲磺酸三甲基硅酯 、 三氟化硼乙醚 作用下， 以 四氢呋喃 、 甲醇 、 乙二醇二甲醚 、 乙醚 、 水 、 乙腈 为溶剂， 反应 30.5h， 生成 A 77636盐酸盐
  参考文献：
  名称：

  The enantioselective synthesis of the potent dopamine D1 agonist (1R,3S)-3-(1'-adamantyl)-1-(aminomethyl)-3,4-dihydro-5,6-dihydroxy-1H-2-benzopyran (A77636)

  摘要：

  The synthesis of both enantiomers of the title compound is described. The corresponding racemic compound (+/-)-1 was previously shown to be a highly potent and selective dopamine Dl agonist. Key to the synthesis of the enantiomers was the oxazaborolidine-catalyzed asymmetric reduction of the alpha-bromomethyl ketone 12 which led to the optically enriched epoxide 7. An aryllithium addition to the epoxide followed by a diastereospecific cyclization to the isochroman system furnished compound 17, which was deprotected to afford (-)-1 with >99.5% optical purity.

  DOI：

  10.1021/jo00052a025
• 作为产物：
  描述：

  1-金刚烷基溴甲酮 在 1-aza-2-boro-3-oxa-1,4,4-triphenylbicyclo<3.3.0>octane 硼烷四氢呋喃络合物 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 生成 (1R)-1-(1'-adamantyl)-2-bromo-1-hydroxyethane
  参考文献：
  名称：

  The enantioselective synthesis of the potent dopamine D1 agonist (1R,3S)-3-(1'-adamantyl)-1-(aminomethyl)-3,4-dihydro-5,6-dihydroxy-1H-2-benzopyran (A77636)

  摘要：

  The synthesis of both enantiomers of the title compound is described. The corresponding racemic compound (+/-)-1 was previously shown to be a highly potent and selective dopamine Dl agonist. Key to the synthesis of the enantiomers was the oxazaborolidine-catalyzed asymmetric reduction of the alpha-bromomethyl ketone 12 which led to the optically enriched epoxide 7. An aryllithium addition to the epoxide followed by a diastereospecific cyclization to the isochroman system furnished compound 17, which was deprotected to afford (-)-1 with >99.5% optical purity.

  DOI：

  10.1021/jo00052a025

文献信息

• US5591884A
  申请人：——

  公开号：US5591884A

  公开（公告）日：1997-01-07
• US5621133A
  申请人：——

  公开号：US5621133A

  公开（公告）日：1997-04-15
• [EN] DOPAMINE AGONISTS<br/>[FR] AGONISTES DE DOPAMINE
  申请人：ABBOTT LABORATORIES

  公开号：WO1996038435A1

  公开（公告）日：1996-12-05

  (EN) Novel compounds having formula (I) and the pharmaceutically acceptable salts, esters and amides thereof, wherein A is -O-; R1, R3, R4, R5, R6, R7, R9, R10, X and Y are specifically defined such that X and Y are not both hydrogen; and up to one combination of (a) R2 and R5, (b) R5 and R6, (c) R5 and R7, (d) R6 and R7, and (e) R7 and Y, taken together with the atoms to which they are attached, may form a ring, the compounds being useful for treating dopamine-related neurological, psychological and cardiovascular disorders as well as in the treatment of cognitive impairment, attention deficit disorder, and substance abuse and other addictive behavior disorders. Also disclosed are intermediates and processes useful in the preparation of the above compounds.(FR) Nouveaux composés représentés par la formule (I), ainsi que leurs sels, esters et amides acceptables pharmaceutiquement, où A représente -O-; R1, R3, R4, R5, R6, R7, R9, R10, X et Y sont définis spécifiquement, de sorte que X et Y ne sont pas tous deux hydrogène; et une combinaison au plus de (a) R2 et R5, (b) R5 et R6, (c) R5 et R7, (d) R6 et R7 et (e) R7 et Y, avec les atomes auxquels ils sont fixés, peut constituer un noyau. Ces composés sont utiles pour traiter les troubles neurologiques, psychologiques et cardio-vasculaires associés à la dopamine, ainsi que l'altération cognitive, le déficit de l'attention, la toxicomanie et d'autres troubles de comportement provoqués par la dépendance. L'invention concerne également des intermédiaires et des procédés utiles pour la préparation desdits composés.
• The enantioselective synthesis of the potent dopamine D1 agonist (1R,3S)-3-(1'-adamantyl)-1-(aminomethyl)-3,4-dihydro-5,6-dihydroxy-1H-2-benzopyran (A77636)
  作者：Michael P. DeNinno、Richard J. Perner、Howard E. Morton、Stanley DiDomenico

  DOI：10.1021/jo00052a025

  日期：1992.12

  The synthesis of both enantiomers of the title compound is described. The corresponding racemic compound (+/-)-1 was previously shown to be a highly potent and selective dopamine Dl agonist. Key to the synthesis of the enantiomers was the oxazaborolidine-catalyzed asymmetric reduction of the alpha-bromomethyl ketone 12 which led to the optically enriched epoxide 7. An aryllithium addition to the epoxide followed by a diastereospecific cyclization to the isochroman system furnished compound 17, which was deprotected to afford (-)-1 with >99.5% optical purity.