4-[(R)-(6-Chloro-2,5-diphenyl-pyrimidin-4-yloxy)-((2S,4S,5R)-5-ethyl-1-aza-bicyclo[2.2.2]oct-2-yl)-methyl]-6-triisopropylsilanyloxy-quinoline | 914379-06-9

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 金鸡纳生物碱
• 英文名称: 4-[(R)-(6-Chloro-2,5-diphenyl-pyrimidin-4-yloxy)-((2S,4S,5R)-5-ethyl-1-aza-bicyclo[2.2.2]oct-2-yl)-methyl]-6-triisopropylsilanyloxy-quinoline
• CAS: 914379-06-9
• 化学式: C₄₄H₅₃ClN₄O₂Si
• 分子量: 733.469
• InChiKey: ZTRBKESDXUBEHN-SNVASPJLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.81
• 重原子数：
  52.0
• 可旋转键数：
  12.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  60.37
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  4-[(R)-(6-Chloro-2,5-diphenyl-pyrimidin-4-yloxy)-((2S,4S,5R)-5-ethyl-1-aza-bicyclo[2.2.2]oct-2-yl)-methyl]-6-triisopropylsilanyloxy-quinoline 在 氢氟酸 作用下， 以 水 、 乙腈 为溶剂， 反应 0.5h， 以400 mg的产率得到
  参考文献：
  名称：

  Structure Reassignment and Synthesis of Jenamidines A₁/A₂, Synthesis of (+)-NP25302, and Formal Synthesis of SB-311009 Analogues

  摘要：

  and C (8-10). Jenamidines A(1)/A(2) (8) were synthesized from activated proline derivative 43 by conversion to 26 in two steps and 50% overall yield. Acylation of 26 with acid chloride 38d gave 39d, which was deprotected with TFA and then mild base to give 8 in 45% yield from 26. (-)-trans-2,5-Dimethylproline ethyl ester (49) was prepared by the enantioselective Michael reaction of ethyl 2-nitropropionate (51) and methyl vinyl ketone (50) using modified dihydroquinine 60 as the catalyst. Further elaboration converted 49 to natural (+)-NP25302 (12). A Wittig reaction of proline NCA ( 76) with ylide 79 gave 72 as a 9/1 E/Z mixture in 27% yield, completing a one-step formal synthesis of SB-311009 analogues.

  DOI：

  10.1021/jo061650+
• 作为产物：
  描述：

  三异丙基氯硅烷 在 咪唑 、 氢氧化钾 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 1.0h， 生成 4-[(R)-(6-Chloro-2,5-diphenyl-pyrimidin-4-yloxy)-((2S,4S,5R)-5-ethyl-1-aza-bicyclo[2.2.2]oct-2-yl)-methyl]-6-triisopropylsilanyloxy-quinoline
  参考文献：
  名称：

  Structure Reassignment and Synthesis of Jenamidines A₁/A₂, Synthesis of (+)-NP25302, and Formal Synthesis of SB-311009 Analogues

  摘要：

  and C (8-10). Jenamidines A(1)/A(2) (8) were synthesized from activated proline derivative 43 by conversion to 26 in two steps and 50% overall yield. Acylation of 26 with acid chloride 38d gave 39d, which was deprotected with TFA and then mild base to give 8 in 45% yield from 26. (-)-trans-2,5-Dimethylproline ethyl ester (49) was prepared by the enantioselective Michael reaction of ethyl 2-nitropropionate (51) and methyl vinyl ketone (50) using modified dihydroquinine 60 as the catalyst. Further elaboration converted 49 to natural (+)-NP25302 (12). A Wittig reaction of proline NCA ( 76) with ylide 79 gave 72 as a 9/1 E/Z mixture in 27% yield, completing a one-step formal synthesis of SB-311009 analogues.

  DOI：

  10.1021/jo061650+