(R)-4-hydroxymethyl-2-methyl-2-oxazoline | 61999-31-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑啉类
• 英文名称: (R)-4-hydroxymethyl-2-methyl-2-oxazoline
• 英文别名: (R)-4-(hydroxymethyl)-2-methyloxazoline；((R)-2-methyl-4,5-dihydro-oxazol-4-yl)-methanol；(2-methyl-4,5-dihydro-oxazol-4-yl)-methanol；(4R)-(+)-2-Methyl-4-hydroxymethyl-2-oxazolin；(4R)-4-(Hydroxymethyl)-2-methyl-2-oxazolin；[(4R)-2-methyl-4,5-dihydro-1,3-oxazol-4-yl]methanol
• CAS: 61999-31-3
• 化学式: C₅H₉NO₂
• 分子量: 115.132
• InChiKey: XMRIIMZQUDHJLK-RXMQYKEDSA-N

物化性质

• 沸点：
  56-59 °C(Press: 0.03 Torr)
• 密度：
  1.25±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  8
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  41.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R)-4-hydroxymethyl-2-methyl-2-oxazoline 在 selenium(IV) oxide 、 sodium hydride 作用下， 以 四氢呋喃 、 1,4-二氧六环 为溶剂， 反应 2.0h， 生成 (5S)-5-<(benzyloxy)methyl>-5,6-dihydro-2H-1,4-oxazin-2-one
  参考文献：
  名称：

  Oxidative Rearrangement of 2-Substituted Oxazolines. A Novel Entry to 5,6-Dihydro-2H-1,4-oxazin-2-ones and Morpholin-2-ones

  摘要：

  A novel synthesis of 5,6-dihydro-2H-1,4-oxazin-2-ones by SeO2-promoted oxidative rearrangement of 2-alkyl- and 2-(arylmethyl)oxazolines is described. Yields are good to excellent; (up to 94%) with the highest yields obtained for 2-arylmethyl- and 2-neopentyl-substituted oxazolines. This reaction provides convenient access to novel 5-aryl-substituted dihydrooxazinones in high yield. The latter compounds are important ''chiral glycine'' synthons for asymmetric synthesis of a-amino acids. Since oxazolines are readily derived from carboxylic acids or their equivalents, this oxidative rearrangement constitutes an entry to synthesis of a-amino acids from carboxylic acids. A mechanism is proposed to account for the rearrangement involving a ''nitrilium to acylium'' 1,2-migration.

  DOI：

  10.1021/jo952144f
• 作为产物：
  描述：

  (2S)-4-甲基-3,5-噁唑啉羧酸乙酯 在 bis-(2-methoxyethoxy)-aluminium hydride 作用下， 以 乙醚 、 苯 为溶剂， 生成 (R)-4-hydroxymethyl-2-methyl-2-oxazoline
  参考文献：
  名称：

  Highly stereoselective addition of organolithium reagents to chiral oxazolines. Asymmetric synthesis of 3-substituted alkanoic acids and 3-substituted lactones

  摘要：

  DOI：

  10.1021/jo01327a046

文献信息

• A Family of Mycothiol Analogues
  作者：Spencer Knapp、Benjamin Amorelli、Etzer Darout、Christian C. Ventocilla、Lawrence M. Goldman、Richard A. Huhn、Ellen C. Minnihan

  DOI：10.1081/car-200059965

  日期：2005.3

  A thioglycoside aminotriol scaffold has been elaborated by acylation, reductive alkylation, sulfonation, phosphorylation, and other procedures to produce a library of 40 functionalized thioglycosides that superficially resemble the enzyme-binding portions of the Mycobacterium tuberculosis detoxifier mycothiol and its metabolic congeners. To the extent that these analogues mimic the transition states derived from substrates of the mycothiol-associated enzymes, they might prove useful as inhibitors and, ultimately, as drug leads.
• Meyers,A.I.; Whitten,C.E., Heterocycles, 1976, vol. 4, p. 1687 - 1692
  作者：Meyers,A.I.、Whitten,C.E.

  DOI：——

  日期：——
• Highly stereoselective addition of organolithium reagents to chiral oxazolines. Asymmetric synthesis of 3-substituted alkanoic acids and 3-substituted lactones
  作者：A. I. Meyers、R. Keith Smith、Charles E. Whitten

  DOI：10.1021/jo01327a046

  日期：1979.6
• Oxidative Rearrangement of 2-Substituted Oxazolines. A Novel Entry to 5,6-Dihydro-2<i>H</i>-1,4-oxazin-2-ones and Morpholin-2-ones
  作者：Cynthia M. Shafer、Tadeusz F. Molinski

  DOI：10.1021/jo952144f

  日期：1996.1.1

  A novel synthesis of 5,6-dihydro-2H-1,4-oxazin-2-ones by SeO2-promoted oxidative rearrangement of 2-alkyl- and 2-(arylmethyl)oxazolines is described. Yields are good to excellent; (up to 94%) with the highest yields obtained for 2-arylmethyl- and 2-neopentyl-substituted oxazolines. This reaction provides convenient access to novel 5-aryl-substituted dihydrooxazinones in high yield. The latter compounds are important ''chiral glycine'' synthons for asymmetric synthesis of a-amino acids. Since oxazolines are readily derived from carboxylic acids or their equivalents, this oxidative rearrangement constitutes an entry to synthesis of a-amino acids from carboxylic acids. A mechanism is proposed to account for the rearrangement involving a ''nitrilium to acylium'' 1,2-migration.