(S)-1-benzyloxycarbonyl-2-ethyl-4-piperidone

• 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: (S)-1-benzyloxycarbonyl-2-ethyl-4-piperidone
• 英文别名: benzyl (2S)-2-ethyl-4-oxopiperidine-1-carboxylate
• 化学式: C₁₅H₁₉NO₃
• 分子量: 261.321
• InChiKey: WEIQKOUQSRGZDC-ZDUSSCGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4-甲氧基吡啶 在 甲醇 、 sodium tetrahydroborate 、 copper(I) bromide dimethylsulfide complex 、 (-)-1,2-双((2R,5R)-2,5-二苯基膦)乙烷 作用下， 以 二氯甲烷 为溶剂， 反应 13.75h， 生成 (S)-1-benzyloxycarbonyl-2-ethyl-4-piperidone
  参考文献：
  名称：

  格氏试剂对N杂环受体的高度对映选择性催化加成

  摘要：

  由于手性N-杂环分子支架在药物化学中的重要性，因此备受追捧。这里描述的是第一种通用催化方法，它利用单一催化剂系统，以优异的收率和对映选择性获得了各种手性2和4取代的四氢喹诺酮，二氢4吡啶酮和哌啶酮。

  DOI：

  10.1002/anie.201906237

文献信息

• Catalytic enantioselective conjugate addition of dialkylzinc reagents to N-substituted-2,3-dehydro-4-piperidones
  作者：Radovan Šebesta、Maria Gabriella Pizzuti、Arnold J. Boersma、Adriaan J. Minnaard、Ben L. Feringa

  DOI：10.1039/b417727d

  日期：——

  The first, highly enantioselective, copper/phosphoramidite-catalyzed conjugate addition of dialkylzinc reagents to N-substituted 2,3-dehydro-4-piperidones is described.

  描述了二烷基锌试剂到N-取代的2，3-脱氢-4-哌啶酮的第一次高对映选择性的铜/亚铁酰胺催化的共轭加成反应。
• Multinuclear Catalyst for Copper-Catalyzed Asymmetric Conjugate Addition of Organozinc Reagents
  作者：Kohei Endo、Mika Ogawa、Takanori Shibata

  DOI：10.1002/anie.200906839

  日期：2010.3.22

  A whole lot o' metal: An efficient copper‐catalyzed asymmetric conjugate addition was achieved using a binol‐derived ligand. The catalytic system has a turnover number of 2000, and the excellent catalytic performance could be attributed to the generation of a multinuclear complex such as 1. binol=2,2′‐dihydroxy‐1,1′‐binaphthyl.

  大量金属：使用由多元醇衍生的配体实现了铜的高效催化不对称共轭物的添加。该催化系统的周转数为2000，出色的催化性能可归因于多核络合物（如1）的生成。binol = 2,2'-二羟基-1,1'-联萘基。
• Copper-Catalyzed Asymmetric 1,4-Addition of Alkenyl Alanes to <i>N</i>-Substituted-2-3-dehydro-4-piperidones
  作者：Daniel Müller、Alexandre Alexakis

  DOI：10.1021/ol3004436

  日期：2012.4.6

  Readily available vinyl alanes are used in the Cu-catalyzed asymmetric conjugate addition reaction to N-substituted-2-3-dehydro-4-piperidones. The enhanced reactivity of recently developed and easily prepared phosphine amine ligands in combination with inexpensive Cu(II)naphtenate (CuNp) allows the introduction of a great variety of alkenyl, alkyl, and aryl aluminums in high enantioselectivity.
• Ferrocene phosphane–carbene ligands in Cu-catalyzed enantioselective 1,4-additions of Grignard reagents to α,β-unsaturated carbonyl compounds
  作者：Jana Csizmadiová、Mária Mečiarová、Ambroz Almássy、Branislav Horváth、Radovan Šebesta

  DOI：10.1016/j.jorganchem.2013.03.033

  日期：2013.8

  Chiral ferrocene phosphane-carbenes are good ligands for the copper-catalyzed 1,4-addition of Grignard reagents to various Michael acceptors. The products were obtained in high enantiomeric purity (up to e.r. = 95:5) and excellent regioselectivity (r.r. = 99:1). These ligands are also useful for domino conjugate addition followed by enolate trapping with imine and aldehyde. (C) 2013 Elsevier B.V. All rights reserved.
• NOVEL TETRAHYDROPYRIDOPYRIMIDINES FOR THE TREATMENT AND PROPHYLAXIS OF HEPATITIS B VIRUS INFECTION
  申请人：F. Hoffmann-La Roche AG

  公开号：EP3535262A1

  公开（公告）日：2019-09-11