(R)-2-[N(1)-benzylpiperidin-2-yl]ethanal | 1227062-95-4

• 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: (R)-2-[N(1)-benzylpiperidin-2-yl]ethanal
• 英文别名: 2-[(2R)-1-benzylpiperidin-2-yl]acetaldehyde
• CAS: 1227062-95-4
• 化学式: C₁₄H₁₉NO
• 分子量: 217.311
• InChiKey: GFLCFWIJWNDRSA-CQSZACIVSA-N

物化性质

• 沸点：
  322.0±15.0 °C(Predicted)
• 密度：
  1.031±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (R)-2-[N(1)-benzylpiperidin-2-yl]ethanal 在 20 wt.% Pd(OH)2 on activated carbon 、 potassium tert-butylate 、 氢气 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 64.5h， 生成 2-丙六氢吡啶盐酸盐
  参考文献：
  名称：

  Asymmetric synthesis of piperidines and octahydroindolizines using a one-pot ring-closure/N-debenzylation procedure

  摘要：

  The conjugate addition of an enantiopure lithium amide to a zeta-hydroxy-alpha,beta-unsaturated ester followed by a one-pot ring-closure/N-debenzylation protocol has been used in the asymmetric syntheses of (S)coniine and (R)-delta-coniceine (isolated as the corresponding hydrochloride salts), and (R,R)-1-(hydroxymethyl)octahydroindolizine (the bicyclic fragment of stellettamides A-C). (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.09.038
• 作为产物：
  描述：

  tert-butyl (R,R)-3-[N-benzyl-N-(α-methyl-p-methoxybenzyl)amino]-7-hydroxyheptanoate 在 咪唑 、 草酰氯 、 碘 、 二异丁基氢化铝 、 二甲基亚砜 、 三苯基膦 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 、 乙腈 为溶剂， 反应 38.33h， 生成 (R)-2-[N(1)-benzylpiperidin-2-yl]ethanal
  参考文献：
  名称：

  Asymmetric synthesis of piperidines and octahydroindolizines using a one-pot ring-closure/N-debenzylation procedure

  摘要：

  The conjugate addition of an enantiopure lithium amide to a zeta-hydroxy-alpha,beta-unsaturated ester followed by a one-pot ring-closure/N-debenzylation protocol has been used in the asymmetric syntheses of (S)coniine and (R)-delta-coniceine (isolated as the corresponding hydrochloride salts), and (R,R)-1-(hydroxymethyl)octahydroindolizine (the bicyclic fragment of stellettamides A-C). (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.09.038

文献信息

• Asymmetric Synthesis of Piperidines and Octahydroindolizines
  作者：Stephen Davies、Deri Hughes、Paul Price、Paul Roberts、Angela Russell、Andrew Smith、James Thomson、Oliver Williams

  DOI：10.1055/s-0029-1219346

  日期：2010.3

  The conjugate addition of a homochiral lithium amide to a xi-hydroxy-alpha,beta-unsaturated ester, followed by a one-pot, ring-closure-N-debenzylation protocol has been used in the asymmetric syntheses of (S)-coniine and (R)-delta-coniceine (isolated as the corresponding hydrochloride salts) and the bicyclic core of stellettamide A.
• Asymmetric synthesis of piperidines and octahydroindolizines using a one-pot ring-closure/N-debenzylation procedure
  作者：Stephen G. Davies、Ai M. Fletcher、Deri G. Hughes、James A. Lee、Paul D. Price、Paul M. Roberts、Angela J. Russell、Andrew D. Smith、James E. Thomson、Oliver M.H. Williams

  DOI：10.1016/j.tet.2011.09.038

  日期：2011.12

  The conjugate addition of an enantiopure lithium amide to a zeta-hydroxy-alpha,beta-unsaturated ester followed by a one-pot ring-closure/N-debenzylation protocol has been used in the asymmetric syntheses of (S)coniine and (R)-delta-coniceine (isolated as the corresponding hydrochloride salts), and (R,R)-1-(hydroxymethyl)octahydroindolizine (the bicyclic fragment of stellettamides A-C). (C) 2011 Elsevier Ltd. All rights reserved.