tert-butyl (R)-2-[N(1)-benzylpiperidin-2-yl]acetate | 1227062-91-0

• 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: tert-butyl (R)-2-[N(1)-benzylpiperidin-2-yl]acetate
• 英文别名: tert-butyl (R)-(N-benzylpiperidin-2'-yl)acetate；tert-butyl 2-[(2R)-1-benzylpiperidin-2-yl]acetate
• CAS: 1227062-91-0
• 化学式: C₁₈H₂₇NO₂
• 分子量: 289.418
• InChiKey: SHSGPSHAYMKCPN-MRXNPFEDSA-N

物化性质

• 沸点：
  363.5±15.0 °C(Predicted)
• 密度：
  1.022±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  tert-butyl (R)-2-[N(1)-benzylpiperidin-2-yl]acetate 在 草酰氯 、 potassium tert-butylate 、 二异丁基氢化铝 、 二甲基亚砜 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 22.83h， 生成 (R)-2-allyl-1-benzylpiperidine
  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 、 碘 、 三苯基膦 作用下， 以 甲苯 、 乙腈 为溶剂， 反应 32.0h， 生成 tert-butyl (R)-2-[N(1)-benzylpiperidin-2-yl]acetate
  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
• 作为试剂：
  描述：

  tert-butyl (R,R)-3-[N-benzyl-N-(α-methyl-p-methoxybenzyl)amino]-7-hydroxyheptanoate 在 咪唑 、 tert-butyl (R)-2-[N(1)-benzylpiperidin-2-yl]acetate 、 20 wt.% Pd(OH)2 on activated carbon 、 2,2,6,6-tetramethylpiperidinyl-lithium 、 氢气 、 碘 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 氯仿 、 甲苯 、 乙腈 为溶剂， -78.0~80.0 ℃ 、101.33 kPa 条件下， 反应 113.0h， 生成 tert-butyl (R,R)-3-oxooctahydroindolizine-1-carboxylate
  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.