N-carbobenzoxy-cis-2,6-bis(hydroxymethyl)piperidine | 144433-70-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-carbobenzoxy-cis-2,6-bis(hydroxymethyl)piperidine
• 英文别名: Benzyl (2R,6S)-2,6-bis(hydroxymethyl)piperidine-1-carboxylate；benzyl (2S,6R)-2,6-bis(hydroxymethyl)piperidine-1-carboxylate
• CAS: 144433-70-5
• 化学式: C₁₅H₂₁NO₄
• 分子量: 279.336
• InChiKey: GFDRAYXIIRZWRR-OKILXGFUSA-N

物化性质

• 沸点：
  455.0±20.0 °C(Predicted)
• 密度：
  1.198±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  70
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-carbobenzoxy-cis-2,6-bis(hydroxymethyl)piperidine 在 盐酸 、 palladium 10% on activated carbon 、 potassium tert-butylate 、 氢气 、 戴斯-马丁氧化剂 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 水 为溶剂， 生成 cis-2,6-di-(2-quinolylpiperidine)
  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：

  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

文献信息

• Stereoselective and regioselective synthesis of azepane and azepine derivatives via piperidine ring expansion
  作者：Hyun-soon Chong、Bishwajit Ganguly、Grant A. Broker、Robin D. Rogers、Martin W. Brechbiel

  DOI：10.1039/b204677f

  日期：2002.9.11

  Diastereomerically pure azepane derivatives 5, 13 were prepared by piperidine ring expansion with exclusive stereoselectivity and regioselectivity and in excellent yield. The structure and stereochemistry of 5 were confirmed via X-ray crystallographic analysis. The ring expansion strategy was applied to the construction of an azepine backbone 22 of a potential biologically active compound. The regiochemistry and stereochemistry of the piperidine ring expansion process were investigated by semiempirical molecular orbital calculations.

  通过哌啶扩环法制备了非对映纯氮杂环庚烷衍生物 5 和 13，具有独一无二的立体选择性和区域选择性，而且收率极高。通过 X 射线晶体分析证实了 5 的结构和立体化学性质。扩环策略被应用于构建具有潜在生物活性化合物的氮杂环庚骨架 22。通过半经验分子轨道计算研究了哌啶扩环过程的区域化学和立体化学。
• 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%).
• Enzymatic Route to Chiral, Nonracemic <i>cis</i>-2,6- and <i>cis</i>,<i>cis</i>-2,4,6-Substituted Piperidines. Synthesis of (+)-Dihydropinidine and Dendrobate Alkaloid (+)-241D
  作者：Robert Chênevert、Michael Dickman

  DOI：10.1021/jo9519569

  日期：1996.1.1

  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.
• Enzymatic desymmetrization of meso cis-2,6- and cis,cis-2,4,6-substituted piperidines. Chemoenzymatic synthesis of (5S,9S)-(+)-indolizidine 209D
  作者：Robert Chênevert、Ghodsi Mohammadi Ziarani、Marie Pascale Morin、Mohammed Dasser

  DOI：10.1016/s0957-4166(99)00315-8

  日期：1999.8

  The stereoselective acylation of meso piperidines 3a,b by vinyl acetate (solvent and acyl donor) in the presence of Candida antarctica lipase gave the corresponding (2S,6R) and (2S,4R,6R) monoesters 2a,b in high enantiomeric purity. (5S,9S)-(+)-Indolizidine 209D was prepared in eight steps from (2S,6R)-2a. (C) 1999 Elsevier Science Ltd. All rights reserved.
• A chemoenzymatic-RCM strategy for the enantioselective synthesis of new dihydroxylated 5-hydroxymethyl-indolizidines and 6-hydroxymethyl-quinolizidines
  作者：Giordano Lesma、Alessia Colombo、Nicola Landoni、Alessandro Sacchetti、Alessandra Silvani

  DOI：10.1016/j.tetasy.2007.07.017

  日期：2007.8

  A direct method for the synthesis of new azasugars-like compounds has been developed, which involves a new biocatalytic protocol based on the use of a lipase from Candida Cylindracea and of a ionic liquid as reaction medium, to prepare the key Cl-symmetric piperidine precursor. By subsequent application of RCM reactions and OSO4-catalyzed double bond syn-dihydroxylation, the synthesis of the target compounds could be accomplished in a straightforward and stereocontrolled manner. (c) 2007 Elsevier Ltd. All rights reserved.