(R)-1-Phenyl-2-<(R)-2-pyrrolidinyl>ethanol | 134877-23-9

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (R)-1-Phenyl-2-<(R)-2-pyrrolidinyl>ethanol
• 英文别名: (1R,2'R)-1-phenyl-2-(pyrrolidin-2'-yl)ethanol；(1R)-1-phenyl-2-[(2R)-pyrrolidin-2-yl]ethanol
• CAS: 134877-23-9
• 化学式: C₁₂H₁₇NO
• 分子量: 191.273
• InChiKey: VSDZLESKQMMKLT-VXGBXAGGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  32.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  对硝基苯甲醛 、 (R)-1-Phenyl-2-<(R)-2-pyrrolidinyl>ethanol 以 苯 为溶剂， 生成 (1R,3R)-1-(4-Nitro-phenyl)-3-phenyl-hexahydro-pyrrolo[1,2-c][1,3]oxazine
  参考文献：
  名称：

  Ligand assisted hydride delivery : An expeditious stereoselective total synthesis of (±) nor-sedamine and its pyrrolidino analog

  摘要：

  DOI：

  10.1016/s0040-4039(00)99621-7
• 作为产物：
  描述：

  <(S)-1-Benzyl-2-<(R)-2-((R)-2-hydroxy-2-phenylethyl)-pyrrolidino>-2-oxoethyl>-2,2-dimethylpropionat 在 四丁基氢氧化铵 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 以69%的产率得到(R)-1-Phenyl-2-<(R)-2-pyrrolidinyl>ethanol
  参考文献：
  名称：

  Chelat- und nicht-chelat-kontrollierte reduktionen von β-amido-ketonen: Synthese nicht-racemischer 1,3-aminoalkohole mit pyrrolidinstruktur

  摘要：

  The reduction of the amidoketones (R)-1 and (S)-2 has been achieved in a stereocontrolled manner giving either the product with like- or unlike configuration depending upon the reducing agent employed. Thus with Li(O(t)Bu)3AlH the amidoalcohols (R,R)-3 and (S,S)-5 were the major diastereomers formed whereas with K((s)Bu)3BH (R,S)-4 and (S,R)-6 dominated. Stereoselectivities up to 98/2 were observed. As a mechanistic rationale for the change of direction in the asymmetric induction a chelate- and non-chelate-model have been envoked.By including (rac)-9 in this study having a non chiral acyl group it was found that the chiral auxiliary in (R)-1/(S)-2 is essential for a high asymmetric induction under chelate- but not under non-chelate-control.Hydrolysis of the amidoalcohols provided the corresponding 1,3-aminoalcohols (R,R)-12, (S,S)-12, (R,S)-13 and (S,R)-13. The configuration of these compounds has been assigned by means of H-1 NMR spectroscopy.

  DOI：

  10.1016/s0040-4020(01)96102-2

文献信息

• Asymmetric synthesis of Sedum alkaloids via lithium amide conjugate addition
  作者：Stephen G. Davies、Ai M. Fletcher、Paul M. Roberts、Andrew D. Smith

  DOI：10.1016/j.tet.2009.09.104

  日期：2009.12

  Conjugate addition of lithium (R)-N-allyl-N-(α-methylbenzyl)amide or lithium (R)-N-but-3-enyl-N-(α-methylbenzyl)amide to an alkyl hexa-2,4-dienoate or alkyl hepta-2,6-dienoate, followed by ring-closing metathesis of the olefin functionalities within the resultant β-amino ester, generates a range of diastereoisomerically pure azacycles in good yield. These homochiral templates are readily transformed

  将（R）-N-烯丙基-N-（α-甲基苄基）酰胺锂或（R）-N-丁-3-烯基-N-（α-甲基苄基）酰胺共轭加成至烷基hexa-2,4 -二烯酸酯或7,6-二烯丙基烷基酯，然后在所得β-氨基酯中将烯烃官能团进行闭环复分解，以高收率生成一系列非对映异构纯的氮杂环。这些同手性模板很容易转化为景天家族的一系列哌啶生物碱，以及相应的五元，七元和八元环同系物。