摩熵化学
数据库官网
小程序
打开微信扫一扫
首页 分子通 化学资讯 化学百科 反应查询 关于我们
请输入关键词

(2R,3S)-N,N-diethyl 3-(4-methoxyphenyl)glycidamide

中文名称
——
中文别名
——
英文名称
(2R,3S)-N,N-diethyl 3-(4-methoxyphenyl)glycidamide
英文别名
(2R,3S)-N,N-diethyl-3-(4-methoxyphenyl)oxirane-2-carboxamide
(2R,3S)-N,N-diethyl 3-(4-methoxyphenyl)glycidamide化学式
CAS
——
化学式
C14H19NO3
mdl
——
分子量
249.31
InChiKey
KXBUSYHKFUMZIB-QWHCGFSZSA-N
BEILSTEIN
——
EINECS
——
  • 物化性质
  • 计算性质
  • ADMET
  • 安全信息
  • SDS
  • 制备方法与用途
  • 上下游信息
  • 反应信息
  • 文献信息
  • 表征谱图
  • 同类化合物
  • 相关功能分类
  • 相关结构分类

计算性质

  • 辛醇/水分配系数(LogP):
    1.6
  • 重原子数:
    18
  • 可旋转键数:
    5
  • 环数:
    2.0
  • sp3杂化的碳原子比例:
    0.5
  • 拓扑面积:
    42.1
  • 氢给体数:
    0
  • 氢受体数:
    3

上下游信息

  • 上游原料
    中文名称 英文名称 CAS号 化学式 分子量

反应信息

  • 作为产物:
    描述:
    2-氨基-N,N-二乙基乙酰胺copper acetylacetonate 、 (S)-2'-methoxy-2-methylthio-1,1'-binaphthalene 、 硫酸 、 sodium nitrite 作用下, 以 二氯甲烷 为溶剂, 反应 72.33h, 生成 (2R,3S)-N,N-diethyl 3-(4-methoxyphenyl)glycidamide
    参考文献:
    名称:
    Catalytic asymmetric synthesis of glycidic amides via chiral sulfur ylides
    摘要:
    Reaction of diazoacetamides with aromatic aldehydes in the presence of 20 mol% of chiral binaphthylsulfide and 10 mol% of copper(II) acetylacetonate gave chiral glycidic amides with up to 64% ee. (C) 1999 Elsevier Science Ltd. All rights reserved.
    DOI:
    10.1016/s0957-4166(99)00289-x
点击查看最新优质反应信息

文献信息

  • Highly Enantioselective Synthesis of Glycidic Amides Using Camphor-Derived Sulfonium Salts. Mechanism and Applications in Synthesis
    作者:Varinder K. Aggarwal、Jonathan P. H. Charmant、Daniel Fuentes、Jeremy N. Harvey、George Hynd、Diasuke Ohara、Willy Picoul、Raphaël Robiette、Catherine Smith、Jean-Luc Vasse、Caroline L. Winn
    DOI:10.1021/ja0568345
    日期:2006.2.1
    amide-stabilized sulfur ylides derived from readily available camphor-derived sulfonium salts for the synthesis of glycidic amides have been studied. Primary, secondary, and tertiary amides were tested, and it was found that the highest enantioselectivities were observed with tertiary amides, which provided glycidic amides in good to excellent yields, exclusive trans selectivity, and excellent enantioselectivities
    已经研究了一系列由容易获得的樟脑衍生锍盐衍生的酰胺稳定硫叶立德用于合成缩水甘油酰胺的反应。对伯、仲和叔酰胺进行了测试,发现使用叔酰胺观察到最高的对映选择性,这提供了良好至极好的收率、专属反式选择性和极好的对映选择性的缩水甘油酰胺。该反应对于芳香醛是普遍的,但脂肪醛给出了更多可变的对映选择性。通过用有机锂试剂处理,环氧酰胺可以干净地转化为环氧酮。我们还能够用各种亲核试剂实现环氧酰胺的选择性开环,然后将酰胺水解以产生相应的羧酸。
  • Towards a General Understanding of Carbonyl-Stabilised Ammonium Ylide-Mediated Epoxidation Reactions
    作者:Johanna Novacek、Lukas Roiser、Katharina Zielke、Raphaël Robiette、Mario Waser
    DOI:10.1002/chem.201602052
    日期:2016.8.1
    carbonyl‐stabilised ammonium ylide‐mediated epoxidation reactions were systematically investigated by experimental and computational means and the hereby obtained energy profiles provide explanations for the observed experimental results. In addition, we were able to identify the first tertiary amine‐based chiral auxiliary that allows for high enantioselectivities and high yields for such epoxidation reactions.
    通过实验和计算手段系统地研究了羰基稳定的铵叶立德介导的环氧化反应的关键因素,由此获得的能量分布为观察到的实验结果提供了解释。此外,我们还能够鉴定出第一个基于叔胺的手性助剂,该助剂可实现高对映选择性和高产率,用于此类环氧化反应。
  • Highly Enantioselective Darzens Reaction of a Camphor-Derived Sulfonium Amide to Give Glycidic Amides and Their Applications in Synthesis
    作者:Varinder K. Aggarwal、George Hynd、Willy Picoul、Jean-Luc Vasse
    DOI:10.1021/ja0272540
    日期:2002.8.1
    sulfonium ylide bearing chiral groups on sulfur has been investigated. We have discovered that the camphor-derived amide-stabilized ylide reacts with aldehydes at -50 degrees C in ethanol to give glycidic amides in one step with up to 99% ee and complete diastereoselectivity. From analyzing reactions of different ratios of diastereomers at sulfur it was found that the major diastereomer gave very high
    已经研究了在硫上带有手性基团的酰胺稳定的锍叶立德的反应。我们发现樟脑衍生的酰胺稳定叶立德在 -50 摄氏度的乙醇中与醛反应,一步生成缩水甘油酰胺,ee 高达 99%,完全非对映选择性。通过分析不同比例的非对映异构体在硫处的反应,发现主要的非对映异构体具有非常高的对映选择性,而次要的非对映异构体的选择性要低得多(54% ee)。进一步的机理研究表明,对映选择性不是在甜菜碱形成步骤(CC 键形成是可逆的)中受到控制,而是在两种非对映甜菜碱新形成的 CC 周围键旋转的不同障碍中受到控制。研究了环氧酰胺的进一步转化。发现环氧酰胺可以通过与有机锂试剂反应转化为环氧酮,并且它们可以被亲核试剂使用 Yb(OTf)3 以完全区域选择性开环。该方法的实用性在 SK&F 104353 的合成中得到了例证,SK&F 104353 是一种白三烯 D4 拮抗剂,可用于治疗支气管哮喘。
  • [EN] ASYMMETRIC SYNTHESIS OF GLYCIDIC AMIDES<br/>[FR] SYNTHESE ASYMETRIQUE D'AMIDES GLYCIDIQUES
    申请人:UNIV BRISTOL
    公开号:WO2003087075A1
    公开(公告)日:2003-10-23
    Enantiomerically enriched trans-2,3-epoxyamides of the formula (I) in which R1 is a 1-18C aliphatic hydrocarbyl optionally substituted by one or more substituent groups selected from halo, nitro, phenyl and -ORW, where RW is H, 1-6C alkyl, benzyl or phenyl, or is aryl containing from 6-12 ring carbon atoms which is optionally substituted by one or more substituent groups selected from 1-6C alkyl, halo, nitro, phenyl, benzyl and -ORW, where RW is as defined above, or is a monocyclic or fused bicyclic heterocyclic group containing at least one heteroatom selected from N, O and S which group is optionally substituted by one or more substituent groups selected from 1-6C alkyl, halo, nitro, phenyl, benzyl and -ORW, where RW is as defined above; R2 and R3 are the same or different group selected from H, 1-6C alkyl optionally substituted with one or more substituent groups selected from halo, nitro, phenyl and -ORW, where RW is as defined above, 2-6C alkenyl optionally substituted with one or more substituent groups selected from halo, nitro, phenyl and -ORW, where RW is as defined above, phenyl optionally substituted by one or more substituent groups selected from 1-6C alkyl, halo, nitro, phenyl, benzyl and -ORW, where RW is as defined above, and monocyclic heterocyclic groups containing one or more heteroatoms selected from O, S and N, optionally substituted with one or more substituent groups selected from 1-6C alkyl, halo, nitro, phenyl, benzyl and -ORW, where RW is as defined above or R2 or R3, or R2 or R3, together with the nitrogen atom to which they are attached, form a heterocyclic ring, are made by a method comprising reacting a sulfonium salt of the formula (II) wherein R2 and R3 are as defined above, R4 is a group selected from 1-12C alkyl, 6-12C aryl and 7-13C aralkyl and -SiMe3, R5 is 1-4C alkyl group and X- is a counterion, with an aldehyde of the formula R1CHO, where R1 is as defined above, in a solvent in the presence of a base. The use of this method gives excellent yields of the trans epoxides. Sulfonium salts of the formula (II), as defined above, are also disclosed.
    公式(I)中的对映体富集的trans-2,3-环氧酰胺,其中R1是1-18C脂肪烃基,可选地被一个或多个取代基所取代,所选的取代基包括卤素,硝基,苯基和-ORW,其中RW为H,1-6C烷基,苄基或苯基,或是含有6-12个环碳原子的芳基,可选地被一个或多个取代基所取代,所选的取代基包括1-6C烷基,卤素,硝基,苯基,苄基和-ORW,其中RW如上所定义,或是含有至少一个异原子(N,O和S)的单环或融合双环杂环基团,可选地被一个或多个取代基所取代,所选的取代基包括1-6C烷基,卤素,硝基,苯基,苄基和-ORW,其中RW如上所定义;R2和R3是相同或不同的基团,所选的基团包括H,1-6C烷基,可选地被一个或多个取代基所取代,所选的取代基包括卤素,硝基,苯基和-ORW,其中RW如上所定义,2-6C烯基,可选地被一个或多个取代基所取代,所选的取代基包括卤素,硝基,苯基和-ORW,其中RW如上所定义,苯基,可选地被一个或多个取代基所取代,所选的取代基包括1-6C烷基,卤素,硝基,苯基,苄基和-ORW,其中RW如上所定义,以及含有一个或多个异原子(O,S和N)的单环杂环基团,可选地被一个或多个取代基所取代,所选的取代基包括1-6C烷基,卤素,硝基,苯基,苄基和-ORW,其中RW如上所定义,或R2或R3,或R2或R3与它们连接的氮原子一起形成一个杂环环;通过在碱存在下,在溶剂中反应公式(II)的磺鎵盐,其中R2和R3如上所定义,R4是所选的基团,包括1-12C烷基,6-12C芳基和7-13C芳基烷基和-SiMe3,R5是1-4C烷基,X-是一个计数离子,与公式R1CHO的醛在溶剂中反应来制备这些化合物。使用此方法可获得优异的trans环氧化物收率。公式(II)中的磺鎵盐也被揭示。
  • Meth-Cohn Otto, Horak R. Martinus, Fouche Gerda, J. Chem. Soc. Perkin Trans. 1, (1994) N 11, S 1517-1527
    作者:Meth-Cohn Otto, Horak R. Martinus, Fouche Gerda
    DOI:——
    日期:——
查看更多