-4-(1-methylethyl)-3-(2-methyl-1-oxobutyl)-2-oxazolidinone | 80735-98-4

• 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: -4-(1-methylethyl)-3-(2-methyl-1-oxobutyl)-2-oxazolidinone
• 英文别名: (4S)-3-((2'S)-2'-methylbutanoyl)-4-(1-methylethyl)-2-oxazolidinone；(4S)-3-[(2S)-2-Methylbutyryl]-4-isopropyloxazolidin-2-one；(4S)-3-[(2S)-2-methylbutanoyl]-4-propan-2-yl-1,3-oxazolidin-2-one
• CAS: 80735-98-4
• 化学式: C₁₁H₁₉NO₃
• 分子量: 213.277
• InChiKey: PTLVGXKLHKHRDN-DTWKUNHWSA-N

物化性质

• 沸点：
  323.4±11.0 °C(Predicted)
• 密度：
  1.063±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 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

• 作为产物：
  描述：

  (S)-4-Isopropyl-3-((2R,3R)-2-methyl-3-phenylsulfanyl-butyryl)-oxazolidin-2-one 在 镍 作用下， 以 甲醇 为溶剂， 以94%的产率得到-4-(1-methylethyl)-3-(2-methyl-1-oxobutyl)-2-oxazolidinone
  参考文献：
  名称：

  非对映体区分亲核加成反应在两个连续的立体中心发生不对称诱导

  摘要：

  Distereoface区分苯酚与苯酚的亲核性，提供了一个新的伴随的两个不连续立体中心的不对称结构，并已成功地应用于（+）-地尔硫m的不对称合成。

  DOI：

  10.1016/0040-4039(91)80821-m

文献信息

• Syntheses of isotopically labelled L-α-amino acids with an asymmetric centre at C-3
  作者：John R. Harding、Rachael A. Hughes、Nicholas M. Kelly、Andrew Sutherland、Christine L. Wilis

  DOI：10.1039/b005172l

  日期：——

  Approaches are described to the synthesis of a series of isotopically labelled L-α-amino acids each with an asymmetric centre at C-3, including isoleucine, allo-isoleucine, threonine and allo-threonine. The methods may be simply adapted for the selective incorporation of an isotopic label at each site of L-valine including the selective labelling of either diastereotopic methyl group with carbon-13

  描述了合成一系列同位素标记的L -α-氨基酸的方法，每个氨基酸在C-3处具有不对称中心，包括异亮氨酸， 同种异亮氨酸， 苏氨酸 和 异基因-苏氨酸。所述方法可以简单地适于将同位素标记物选择性地掺入到所述细胞的每个位点。大号缬氨酸 包括对非对映异构体的选择性标记 甲基 碳13和/或氘和 贴标 的 胺 和 氮15。
• Asymmetric alkylation and sulphenylation of chiral O-silylated imide enolates.
  作者：Rikki P. Alexander、Ian Paterson

  DOI：10.1016/s0040-4039(00)95033-0

  日期：1985.1

  The chiral O-silylated enolates (5) can be alkylated or sulphenylated with high diastereoselectivity (∼20:1) by 1,3-dithienium fluoroborate or PhSCl. Phenylthio-alkylation, in contrast, proceeds with low diastereoselectivity.

  手性O-甲硅烷基化的烯醇盐（5）可以被1,3-二氟硼酸二硼鎓或PhSCl高非对映选择性（〜20：1）烷基化或亚磺酰基化。相反，苯硫基烷基化以非对映选择性低的方式进行。
• Asymmetric Diels-Alder cycloaddition reactions with chiral .alpha.,.beta.-unsaturated N-acyloxazolidinones
  作者：David A. Evans、K. T. Chapman、J. Bisaha

  DOI：10.1021/ja00212a037

  日期：1988.2
• Asymmetric alkylation reactions of chiral imide enolates. A practical approach to the enantioselective synthesis of .alpha.-substituted carboxylic acid derivatives
  作者：D. A. Evans、M. D. Ennis、D. J. Mathre

  DOI：10.1021/ja00370a050

  日期：1982.3
• Asymmetric construction of two contiguous stereocenters by diastereoface differentiating addition reaction of thiols to chiral imides: Formal synthesis of (+)-diltiazem
  作者：Okiko Miyata、Tetsuro Shinada、Ichiya Ninomiya、Takeaki Naito

  DOI：10.1016/s0040-4020(96)01191-x

  日期：1997.2

  A high degree of diastereoselectivity has been achieved on the asymmetric construction of two contiguous stereocenters by the conjugate addition of thiols to alpha,beta-unsaturated imides possessing Evans's chiral auxiliary. Addition reactions of thiophenol to chiral E- and Z-2-methylcrotonyl imides 4 proceeded with high diastereoface selectivities. Diastereoselectivities were discussed when E- and Z-imides 4 and 5 were used as the substrates. A successful application was demonstrated by the formal synthesis of a clinically useful cardiac drug, (+)-diltiazem. (C) 1997, Elsevier Science Ltd.