(4S)-N-(3-methylbutanoyl)-4-(1-methylethyl)-2-oxazolidinone | 96930-24-4

• 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-(3-methylbutanoyl)-4-(1-methylethyl)-2-oxazolidinone
• 英文别名: (4S)-4-Isopropyl-3-(3-methylbutanoyl)-1,3-oxazolidin-2-one；(4S)-3-(3-methylbutanoyl)-4-propan-2-yl-1,3-oxazolidin-2-one
• CAS: 96930-24-4
• 化学式: C₁₁H₁₉NO₃
• 分子量: 213.277
• InChiKey: TZFXVYWRBTZTML-SECBINFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 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-(3-methylbutanoyl)-4-(1-methylethyl)-2-oxazolidinone 在 palladium on activated charcoal 、 镍 盐酸 、 氢气 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 水 、 溶剂黄146 为溶剂， -78.0 ℃ 、3.45 MPa 条件下， 反应 0.25h， 生成 L-缬氨酸
  参考文献：
  名称：

  Amination of chiral enolates by dialkyl azodiformates. Synthesis of .alpha.-hydrazino acids and .alpha.-amino acids

  摘要：

  DOI：

  10.1021/ja00280a051
• 作为产物：
  描述：

  (S)-4-异丙基-2-唑烷酮 、 异戊酰氯 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 1.0h， 以95%的产率得到(4S)-N-(3-methylbutanoyl)-4-(1-methylethyl)-2-oxazolidinone
  参考文献：
  名称：

  vinigrol的聚合对映选择性合成，这是一种结构新颖的二萜类化合物，具有有效的血小板聚集抑制和抗高血压特性。1.阴离子共生在辛基亚结构的构建中的应用。

  摘要：

  在0摄氏度存在MgBr（2）.OEt（2）的情况下，构建基块15和36e的耦合以exo立体选择性（3.2：1）进行，比不使用碳氢化合物37e时更有利于获得甲醇37e。加性（exo / endo = 1：5.7）。设置顺式八氢萘55的所有相关立体中心的关键转换是37e的氧阴离子加速的[3,3]-σ重排。一个显着的特征是在结构上强制采用了船状过渡态，该态可用于以全顺式排列方式正确设置四个邻甲硫氨酸氢。由于最初通过埃文斯恶唑烷酮方案对映选择性地安装了异丙基取代基，因此55转化为碘砜62的方法可以通过X射线晶体学确认所有绝对立体化学赋值。没有观察到分子内阴离子环化62以产生三环骨架。这种反应性的缺乏归因于构象因素，该构象因素抑制了正确的S（N）2反应轨迹的实现。

  DOI：

  10.1021/jo0301301

文献信息

• Optically active α-alkylsuccinates from the stereoselective alkylation of chiral imide enolates.
  作者：Antoine Fadel、Jacques Salaün

  DOI：10.1016/s0040-4039(00)82319-9

  日期：1988.1

  The chiral oxazolidinones and were alkylated by methyl bromoacetate, then subsequent removal of the chiral auxiliary provided readily with high stereoselectivity the α-alkylated succinates and . Acyloin condensation and bromination gave the optically active α-t-butylcyclobutanedione .

  用溴乙酸甲酯将手性恶唑烷酮和手性恶唑烷酮和烷基化，然后除去手性助剂，容易提供具有高立体选择性的α-烷基化琥珀酸酯和α-烷基化琥珀酸酯。环糊精缩合和溴化得到光学活性的α-叔丁基环丁二酮。
• Stereoselective Michael Addition Reactions of Acylated Oxazolidinones to Ethyl 3-Trifluoromethylacrylate
  作者：Takashi Yamazaki、Jiro Haga、Tomoya Kitazume

  DOI：10.1246/cl.1991.2175

  日期：1991.12

  Michael addition reactions of acyl oxazolidinones to ethyl 3-trifluoromethylacrylate were found to proceed smoothly with a high degree of diastereo- as well as diastereofacial selectivity at the new carbon–carbon bond.

  发现酰基恶唑烷酮与 3-三氟甲基丙烯酸乙酯的迈克尔加成反应在新的碳-碳键处以高度的非对映选择性和非对映选择性顺利进行。
• Stereoselective Synthesis of Trifluoromethylated Compounds with Controlled Adjacent Tertiary Carbons by Michael Addition to (E)-3-(Trifluoromethyl)acrylates
  作者：Noriyasu Shinohara、Jiro Haga、Takashi Yamazaki、Tomoya Kitazume、Shinichiro Nakamura

  DOI：10.1021/jo00119a013

  日期：1995.7

  Michael addition reaction of various lithium enolates to ethyl (E)-3-(trifluoromethyl)acrylate (E)-1 was found to be one of the most effective routes to construct materials not only with a CF3 group but also with readily distinguishable multiple functionalities by the routine chemical transformations. Particularly, employment of lithium enolates from chiral acyloxazolidinones as Michael donors resulted in the formation of 1,4-adducts, usually with a high degree of diastereoselectivity as well as with a high degree of diastereofacial selectivities only in a single step. Further, it was suggested by both the experimental results and the ab initio calculations that interaction between fluorine-(s) and lithium strongly stabilized the present Michael intermediates, allowing for the smooth reactions even with ketone enolates under kinetically controlled conditions.
• Synthesis of optically active α-phenylselenyl carbonyl derivatives
  作者：Andrew B. Holmes、Alan Nadin、Peter J. O'Hanlon、Neil D. Pearson

  DOI：10.1016/s0957-4166(00)82087-x

  日期：1992.10

  Homochiral silyl enol ethers derived from N-acyl oxazolidinones can be phenyselenylated in high diastereoselectivity and good yield with phenylselenyl chloride. Removal of the chiral auxiliary is accompanied by some epimerisation. leading to isolation of the corresponding alpha-phenylselenyl methyl esters in moderate enantiomeric excess. A slightly improved enantiomeric excess is achieved if 4(S)-benzyl-2-oxazolidinethione 17 is used as a chiral auxiliary.
• Highly Diastereoselective Sequential Enolate-Michael Addition-Ireland Claisen Rearrangement
  作者：Takashi Yamazaki、Noriyasu Shinohara、Tomoya Kitazume、Shoichi Sato

  DOI：10.1021/jo00130a012

  日期：1995.12