cis-(N-benzyloxycarbonyl)-2,6-di-carboxymethyl piperidine | 144433-68-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: cis-(N-benzyloxycarbonyl)-2,6-di-carboxymethyl piperidine
• 英文别名: N-carbobenzoxy-cis-2,6-bis(methoxycarbonyl)piperidine；1-O-benzyl 2-O,6-O-dimethyl (2S,6R)-piperidine-1,2,6-tricarboxylate
• CAS: 144433-68-1
• 化学式: C₁₇H₂₁NO₆
• 分子量: 335.357
• InChiKey: VLFVAHUMHYFTQO-OKILXGFUSA-N

物化性质

• 沸点：
  438.8±45.0 °C(Predicted)
• 密度：
  1.237±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  82.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  cis-(N-benzyloxycarbonyl)-2,6-di-carboxymethyl piperidine 在 锂硼氢 作用下， 以 四氢呋喃 为溶剂， 以81%的产率得到N-carbobenzoxy-cis-2,6-bis(hydroxymethyl)piperidine
  参考文献：
  名称：

  Efficient synthesis of cis-2,6-di-(2-quinolylpiperidine)

  摘要：

  An efficient synthesis of cis-2,6-di-(2-quinolylpiperidine) has been developed. The key steps involve Wittig reaction of N-Cbz-protected cis-piperidine-2,6-dicarboxaldehyde (3) with 2-(triphenylphosphinylmethyl)quinoline bromide (4) and sequential removal of the N-Cbz group and double bond reduction. This synthetic procedure provides an efficient preparation for this useful norlobelane analogue. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.07.067
• 作为产物：
  描述：

  4-氧代-1,4-二氢-2,6-吡啶二甲酸 在 Rh/Al₂O₃ 盐酸 、 氢气 、 N,N-二异丙基乙胺 、 2,2-二甲氧基丙烷 作用下， 以 四氢呋喃 、 水 为溶剂， 25.0 ℃ 、103.42 kPa 条件下， 反应 23.0h， 生成 cis-(N-benzyloxycarbonyl)-2,6-di-carboxymethyl piperidine
  参考文献：
  名称：

  Enzymatic Route to Chiral, Nonracemic cis-2,6- and cis,cis-2,4,6-Substituted Piperidines. Synthesis of (+)-Dihydropinidine and Dendrobate Alkaloid (+)-241D

  摘要：

  Piperidine-based compounds are an important class of natural alkaloids found in plants, insects, and amphibians. A general asymmetric synthesis of 2-alkyl-6-methylpiperidines is presented via the enzymatic desymmetrization of meso cis-2,6- and cis,cis-2,4,6-substituted piperidines with Aspergillus niger lipase(ANL). The enzymatic reaction proceeds in excellent chemical yield and high enantiotopic selectivity (ee greater than or equal to 98%). The general method is used to effect the synthesis of (+)-dihydropinidine-HCl as well as the first asymmetric synthesis of dendrobate alkaloid (+)-241D.

  DOI：

  10.1021/jo9519569

文献信息

• Enzyme-catalysed hydrolysis of N-benzyloxycarbonyl-cis-2,6-(acetoxymethyl)piperidine. A facile route to optically active piperidines
  作者：Robert Chênevert、Michael Dickman

  DOI：10.1016/s0957-4166(00)86034-6

  日期：1992.8

  We report the first enzymatic asymmetrization of a piperidine system. Hydrolysis of N-benzyloxycarbonyl-cis-2,6-(acetoxymethyl)piperidine in the presence of Aspergillus niger lipase gave the corresponding 2R, 6S mono-acetate in good chemical yield and very high optical purity (ee greater-than-or-equal-to 98%).
• Synthesis of symmetrical 1,5-disubstituted granatanines
  作者：Ashish P. Vartak、Linda P. Dwoskin、Peter A. Crooks

  DOI：10.1016/j.tetlet.2008.08.066

  日期：2008.10

  A general entry into symmetrical 1,5-disubstituted granatanines that involves an alkylative ring-closure on a 2,6-bis enolate piperidine intermediate is described. (c) 2008 Elsevier Ltd. All rights reserved.