1,3-bis[(2R)-piperidin-2-yl]propan-2-yloxy-tert-butyl-dimethylsilane | 482376-76-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 1,3-bis[(2R)-piperidin-2-yl]propan-2-yloxy-tert-butyl-dimethylsilane
• CAS: 482376-76-1
• 化学式: C₁₉H₄₀N₂OSi
• 分子量: 340.625
• InChiKey: RHBKZLDOYXLORY-IAGOWNOFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.44
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  33.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1,3-bis[(2R)-piperidin-2-yl]propan-2-yloxy-tert-butyl-dimethylsilane 在 palladium on activated charcoal 盐酸 、 4 A molecular sieve 、 三乙胺 、 pyridinium chlorochromate 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 为溶剂， 反应 20.0h， 生成 di-(tert-butoxycarbonyl)-anaferine
  参考文献：
  名称：

  Enantioselective Synthesis of (−)-Anaferine Dihydrochloride by a Ruthenium-Catalysed Tandem Ring Rearrangement Metathesis

  摘要：

  A stereoselective synthesis of (-)-anaferine dihydrochloride has been developed. The bis(tetrahydropyridine) system 10 was formed by a tandem ring rearrangement metathesis of the chiral bis(but-3-enylamino)cycloheptene derivative 9. (-)-Anaferine dihydrochloride was obtained in 23% overall yield in eleven steps and its absolute configuration was confirmed as (R,R) by this total synthesis.

  DOI：

  10.1002/1099-0690(200208)2002:16<2855::aid-ejoc2855>3.0.co;2-1
• 作为产物：
  描述：

  (1R,4S,6S)-4-acetoxy-6-[(tert-butyldimethylsilyl)oxy]-2-cyclohepten-1-ol 在 palladium on activated charcoal 吡啶 、 甲醇 、 potassium cyanide 、 Grubbs catalyst first generation 、 氢气 、 potassium carbonate 、 甲基磺酰氯 、 苯硫酚 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 117.5h， 生成 1,3-bis[(2R)-piperidin-2-yl]propan-2-yloxy-tert-butyl-dimethylsilane
  参考文献：
  名称：

  Enantioselective Synthesis of (−)-Anaferine Dihydrochloride by a Ruthenium-Catalysed Tandem Ring Rearrangement Metathesis

  摘要：

  A stereoselective synthesis of (-)-anaferine dihydrochloride has been developed. The bis(tetrahydropyridine) system 10 was formed by a tandem ring rearrangement metathesis of the chiral bis(but-3-enylamino)cycloheptene derivative 9. (-)-Anaferine dihydrochloride was obtained in 23% overall yield in eleven steps and its absolute configuration was confirmed as (R,R) by this total synthesis.

  DOI：

  10.1002/1099-0690(200208)2002:16<2855::aid-ejoc2855>3.0.co;2-1

文献信息

• Enantioselective Synthesis of (−)-Anaferine Dihydrochloride by a Ruthenium-Catalysed Tandem Ring Rearrangement Metathesis
  作者：Siegfried Blechert、Christian Stapper

  DOI：10.1002/1099-0690(200208)2002:16<2855::aid-ejoc2855>3.0.co;2-1

  日期：2002.8

  A stereoselective synthesis of (-)-anaferine dihydrochloride has been developed. The bis(tetrahydropyridine) system 10 was formed by a tandem ring rearrangement metathesis of the chiral bis(but-3-enylamino)cycloheptene derivative 9. (-)-Anaferine dihydrochloride was obtained in 23% overall yield in eleven steps and its absolute configuration was confirmed as (R,R) by this total synthesis.