(4S)-N-[(3S)-methylheptanoyl]-4-phenyl-1,3-oxazolidin-2-one | 463304-45-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: (4S)-N-[(3S)-methylheptanoyl]-4-phenyl-1,3-oxazolidin-2-one
• 英文别名: N-(3'S-methylheptanoyl)-4S-phenyl-1,3-oxazolidin-2-one；2-Oxazolidinone, 3-[(3S)-3-methyl-1-oxoheptyl]-4-phenyl-, (4R)-；(4R)-3-[(3S)-3-methylheptanoyl]-4-phenyl-1,3-oxazolidin-2-one
• CAS: 463304-45-2
• 化学式: C₁₇H₂₃NO₃
• 分子量: 289.375
• InChiKey: PCJZVYVNRUNANA-ZFWWWQNUSA-N

物化性质

• 熔点：
  58-60 °C
• 沸点：
  442.0±34.0 °C(Predicted)
• 密度：
  1.103±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (4S)-N-[(3S)-methylheptanoyl]-4-phenyl-1,3-oxazolidin-2-one 在 锂硼氢 作用下， 以 乙醚 为溶剂， 生成 (S)-3-methylheptanal
  参考文献：
  名称：

  The Remarkable Ability of Lithium Ion To Reverse the Stereoselectivity in the Conjugate Addition of Li[BuCuI] to a Chiral N-Crotonyl-2-oxazolidinone

  摘要：

  [GRAPHICS]The influence of lithium ions on the conjugate addition of the monoorganocuprate reagent, Li[BuCuI], to a chiral crotonate has been investigated. The results show that iodotrimethylsilane (TMSI) is crucial for the asymmetric conjugate addition of the copper reagent, but only in THF or when 12-crown-4 is used. The reaction is thought not to involve any halosilane in any critical steps in the organocopper mechanisms conducted in Et2O.

  DOI：

  10.1021/ol035453y
• 作为产物：
  描述：

  (E)-Hept-2-enoyl chloride 在 正丁基锂 、 copper iodide - dimethyl sulfide complex 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 为溶剂， 反应 4.91h， 生成 (4S)-N-[(3S)-methylheptanoyl]-4-phenyl-1,3-oxazolidin-2-one
  参考文献：
  名称：

  单有机铜试剂向手性酰亚胺的高度非对映选择性共轭加成

  摘要：

  描述了使用各种单有机铜酸盐试剂Li [RCuI]向手性N-烯酰基酰胺上的立体选择性缀合物加成。在THF中添加Li [RCuI]时，TMSI的存在提供了最高的立体选择性。在醚或常规的铜促进的格氏试剂中使用Li [RCuI]可获得相反的主要非对映异构体比率。呈现支持的结果的青睐抗-小号-顺使用Li的基板的构象[RCuI] / TMSI在THF中，而铜促进的格氏试剂或锂[RCuI]试剂在醚有利于相对顺式-小号-顺构象。研究了锂离子对单有机铜试剂Li [BuCuI]的立体选择性共轭加成的影响，并提出了两种不同的机理途径。结果表明，碘三甲基硅烷（TMSI）对于铜试剂的不对称共轭添加至关重要，但仅在THF中或使用12-crown-4时才重要。认为该反应在醚中进行的有机铜机理的任何关键步骤中均不涉及任何卤代硅烷。（CuI）4（SMe 2）3复合物前体在使用单有机铜试剂的共轭物加成中起重要作用。

  DOI：

  10.1016/j.tet.2003.12.049

文献信息

• Diastereoselective addition of monoorganocuprates to a chiral fumarate: reaction development and synthesis of (−)-dihydroprotolichesterinic acid
  作者：J. Caleb Hethcox、Charles S. Shanahan、Stephen F. Martin

  DOI：10.1016/j.tet.2015.05.023

  日期：2015.9

  Recent studies of diastereoselective conjugate additions of monoorganocuprates, Li[RCuI], to chiral γ-alkoxycrotonates and fumarates are disclosed. This methodology was applied to the shortest total synthesis of (−)-dihydroprotolichesterinic acid to date, but several attempts to prepare other succinate-derived natural products, such as pilocarpine and antrodin E, were unsuccessful.

  公开了对单有机单酸酯Li [RCuI]的非对映选择性共轭加成到手性γ-烷氧基巴豆酸酯和富马酸酯的最新研究。该方法已应用于迄今为止最短的（-）-dihydroprotolichesterinic acid的全合成，但未能成功制备其他由琥珀酸酯衍生的天然产物，例如毛果芸香碱和antrodinE。
• Asymmetric conjugate additions of TMSI promoted monoorganocuprate reagents, Li[RCuI], to various N-enoyl oxazolidinones
  作者：Patrick Pollock、Jesse Dambacher、Robert Anness、Mikael Bergdahl

  DOI：10.1016/s0040-4039(02)00646-9

  日期：2002.5

  Diastereoselective conjugate additions to different α,β-unsaturated N-acyl oxazolidinones using various monoorganocuprate reagents, Li[RCuI], are described. The TMSI activated conjugate addition reactions provided high yields (80–98%) and reversed major diastereomers (70–96% de) compared to the conventional copper(I)-promoted additions of Grignard reagents or the addition of Li[RCuI] to precomplexed MgBr2/imides

  描述了使用各种单有机铜酸盐试剂Li [RCuI]向不同的α，β-不饱和N-酰基恶唑烷酮类化合物的非对映选择性共轭加成。与常规铜（I）促进的格氏试剂或Li [RCuI]的预配合物相比，TMSI活化的共轭物加成反应可提供高收率（80–98％）并逆转主要非对映异构体（70–96％de） MgBr 2 /酰亚胺。
• Highly diastereoselective conjugate additions of monoorganocopper reagents to chiral imides
  作者：Jesse Dambacher、Robert Anness、Patrick Pollock、Mikael Bergdahl

  DOI：10.1016/j.tet.2003.12.049

  日期：2004.2

  Grignard reagents or the Li[RCuI] reagents in ether favor the opposite syn-s-cis conformation. Influence of lithium ions on the stereoselective conjugate addition of the monoorganocuprate reagent, Li[BuCuI], has been investigated and two different mechanistic pathways are presented. The results show that iodotrimethylsilane (TMSI) is crucial for the asymmetric conjugate addition of the copper reagent, but

  描述了使用各种单有机铜酸盐试剂Li [RCuI]向手性N-烯酰基酰胺上的立体选择性缀合物加成。在THF中添加Li [RCuI]时，TMSI的存在提供了最高的立体选择性。在醚或常规的铜促进的格氏试剂中使用Li [RCuI]可获得相反的主要非对映异构体比率。呈现支持的结果的青睐抗-小号-顺使用Li的基板的构象[RCuI] / TMSI在THF中，而铜促进的格氏试剂或锂[RCuI]试剂在醚有利于相对顺式-小号-顺构象。研究了锂离子对单有机铜试剂Li [BuCuI]的立体选择性共轭加成的影响，并提出了两种不同的机理途径。结果表明，碘三甲基硅烷（TMSI）对于铜试剂的不对称共轭添加至关重要，但仅在THF中或使用12-crown-4时才重要。认为该反应在醚中进行的有机铜机理的任何关键步骤中均不涉及任何卤代硅烷。（CuI）4（SMe 2）3复合物前体在使用单有机铜试剂的共轭物加成中起重要作用。
• The Remarkable Ability of Lithium Ion To Reverse the Stereoselectivity in the Conjugate Addition of Li[BuCuI] to a Chiral <i>N</i>-Crotonyl-2-oxazolidinone
  作者：Jesse Dambacher、Mikael Bergdahl

  DOI：10.1021/ol035453y

  日期：2003.9.1

  [GRAPHICS]The influence of lithium ions on the conjugate addition of the monoorganocuprate reagent, Li[BuCuI], to a chiral crotonate has been investigated. The results show that iodotrimethylsilane (TMSI) is crucial for the asymmetric conjugate addition of the copper reagent, but only in THF or when 12-crown-4 is used. The reaction is thought not to involve any halosilane in any critical steps in the organocopper mechanisms conducted in Et2O.