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(S)-3-ethoxycarbonylamino-4-tert-butyl-2-oxazolidinone

中文名称
——
中文别名
——
英文名称
(S)-3-ethoxycarbonylamino-4-tert-butyl-2-oxazolidinone
英文别名
ethyl N-[(4S)-4-tert-butyl-2-oxo-1,3-oxazolidin-3-yl]carbamate
(S)-3-ethoxycarbonylamino-4-tert-butyl-2-oxazolidinone化学式
CAS
——
化学式
C10H18N2O4
mdl
——
分子量
230.264
InChiKey
KEVCZFQGBPLSGY-SSDOTTSWSA-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):
    2
  • 重原子数:
    16
  • 可旋转键数:
    3
  • 环数:
    1.0
  • sp3杂化的碳原子比例:
    0.8
  • 拓扑面积:
    67.9
  • 氢给体数:
    1
  • 氢受体数:
    4

反应信息

  • 作为产物:
    描述:
    参考文献:
    名称:
    A General Organocatalyst for Direct α-Functionalization of Aldehydes:  Stereoselective C−C, C−N, C−F, C−Br, and C−S Bond-Forming Reactions. Scope and Mechanistic Insights
    摘要:
    The development of a general organocatalyst for the alpha-functionalization of aldehydes, via an enamine intermediate, is presented. Based on optically active alpha,alpha-diarylprolinol silyl ethers, the scope and applications of this catalyst for the stereogenic formation of C-C, C-N, C-F, C-Br, and C-S bonds are outlined. The reactions all proceed in good to high yields and with excellent enantioselectivities. Furthermore, we will present mechanistic insight into the reaction course applying nonlinear effect studies, kinetic resolution, and computational investigations leading to an understanding of the properties of the alpha,alpha-diarylprolinol silyl ether catalysts.
    DOI:
    10.1021/ja056120u
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文献信息

  • Aminal-Pyrrolidine Organocatalysts - Highly Efficient and Modular Catalysts for α-Functionalization of Carbonyl Compounds
    作者:Adrien Quintard、Sébastien Belot、Estelle Marchal、Alexandre Alexakis
    DOI:10.1002/ejoc.200901283
    日期:2010.2
    2-position, gave a synergistic effect leading to two powerful complementary organocatalysts. They show excellent enantiocontrol in the -functionalization of a wide range of linear/branched aldehydes and ketones, including Michael additions to ethenediyl disulfones or nitrostyrene and -amination. We obtained ees up to 98.5 % with low catalyst loadings (down to 1 mol-%). As a proof of efficiency, TOFs of up to
    羟基脯氨酸的 4-位被 aphenol 基团取代,连同 2-位上的氨基,产生协同效应,产生两种强大的互补有机催化剂。它们在广泛的线性/支化醛和酮的 - 官能化中表现出出色的对映控制,包括迈克尔加成到乙二基二砜或硝基苯乙烯和 - 胺化。我们以低催化剂负载量(低至 1 mol%)获得了高达 98.5% 的 ees。作为效率的证明,可以获得高达 1000 h-1 的 TOF。
  • Direct Organo-Catalytic Asymmetricα-Amination of Aldehydes—A Simple Approach to Optically Activeα-Amino Aldehydes,α-Amino Alcohols, andα-Amino Acids
    作者:Anders Bøgevig、Karsten Juhl、Nagaswamy Kumaragurubaran、Wei Zhuang、Karl Anker Jørgensen
    DOI:10.1002/1521-3773(20020517)41:10<1790::aid-anie1790>3.0.co;2-y
    日期:2002.5.17
  • Unusual Reversal of Enantioselectivity in the Proline-Mediated α-Amination of Aldehydes Induced by Tertiary Amine Additives
    作者:Donna G. Blackmond、Antonio Moran、Matthew Hughes、Alan Armstrong
    DOI:10.1021/ja102718x
    日期:2010.6.9
    An intriguing reversal in product enantioselectivity accompanied by a change in the kinetic profile is observed in the alpha-amination of aldehydes catalyzed by proline in the presence of organic bases. Implications for the prevailing stereochemical models for proline and related aminocatalytic transformations are discussed.
  • A General Organocatalyst for Direct α-Functionalization of Aldehydes:  Stereoselective C−C, C−N, C−F, C−Br, and C−S Bond-Forming Reactions. Scope and Mechanistic Insights
    作者:Johan Franzén、Mauro Marigo、Doris Fielenbach、Tobias C. Wabnitz、Anne Kjærsgaard、Karl Anker Jørgensen
    DOI:10.1021/ja056120u
    日期:2005.12.1
    The development of a general organocatalyst for the alpha-functionalization of aldehydes, via an enamine intermediate, is presented. Based on optically active alpha,alpha-diarylprolinol silyl ethers, the scope and applications of this catalyst for the stereogenic formation of C-C, C-N, C-F, C-Br, and C-S bonds are outlined. The reactions all proceed in good to high yields and with excellent enantioselectivities. Furthermore, we will present mechanistic insight into the reaction course applying nonlinear effect studies, kinetic resolution, and computational investigations leading to an understanding of the properties of the alpha,alpha-diarylprolinol silyl ether catalysts.
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