(1R,3S)-3-(1'-adamantyl)-5,6-(cyclohexylidenedioxy)-3,4-dihydro-1-<(N-formylamino)methyl>-1H-2-benzopyran | 145238-46-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: (1R,3S)-3-(1'-adamantyl)-5,6-(cyclohexylidenedioxy)-3,4-dihydro-1-<(N-formylamino)methyl>-1H-2-benzopyran
• 英文别名: (1R,3S)-3-(1'-adamantyl)-5,6-(cyclohexylidenedioxy)-3,4-dihydro-1-[(N-formylamino)methyl]-1H-2-benzopyran；N-[[(6R,8S)-8-(1-adamantyl)spiro[8,9-dihydro-6H-[1,3]dioxolo[4,5-f]isochromene-2,1'-cyclohexane]-6-yl]methyl]formamide
• CAS: 145238-46-6
• 化学式: C₂₇H₃₅NO₄
• 分子量: 437.579
• InChiKey: ODKQNFLQYLXUDX-ZFOSPYDSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  32
• 可旋转键数：
  3
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  56.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1R,3S)-3-(1'-adamantyl)-5,6-(cyclohexylidenedioxy)-3,4-dihydro-1-<(N-formylamino)methyl>-1H-2-benzopyran 在 盐酸 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 乙二醇二甲醚 、 水 为溶剂， 反应 6.0h， 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-(1-Adamantyl)-2-spiro[1,3-benzodioxole-2,1'-cyclohexane]-4-ylethanone 在 proline-derived oxazaborolidine 硼烷四氢呋喃络合物 、 三氟甲磺酸三甲基硅酯 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 2.0h， 生成 (1R,3S)-3-(1'-adamantyl)-5,6-(cyclohexylidenedioxy)-3,4-dihydro-1-<(N-formylamino)methyl>-1H-2-benzopyran
  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

• 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.