(4S,2'S,3'R)-(-)-4-isopropyl-2-(3'-phenyloxiranyl)-4,5-dihydrooxazole | 432504-75-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (4S,2'S,3'R)-(-)-4-isopropyl-2-(3'-phenyloxiranyl)-4,5-dihydrooxazole
• 英文别名: (1R,2S,4'S)-(+)-2-(4-isopropyl-2-oxazolin-2-yl)-styrenoxide；(4S)-2-[(2S,3R)-3-phenyloxiran-2-yl]-4-propan-2-yl-4,5-dihydro-1,3-oxazole
• CAS: 432504-75-1
• 化学式: C₁₄H₁₇NO₂
• 分子量: 231.294
• InChiKey: WHMMPYUJQQFGKV-UPJWGTAASA-N

物化性质

• 沸点：
  340.5±42.0 °C(Predicted)
• 密度：
  1.22±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (4S,2'S,3'R)-(-)-4-isopropyl-2-(3'-phenyloxiranyl)-4,5-dihydrooxazole 在 四甲基乙二胺 、 仲丁基锂 作用下， 以 四氢呋喃 、 乙醚 、 环己烷 为溶剂， 生成 (3S,5S,8R,9S)-3-isopropyl-9-methyl-7,7,8-triphenyl-8,9-epoxy-1,6-dioxa-4-azaspiro[4.4]nonane
  参考文献：
  名称：

  Stereospecific β-Lithiation of Oxazolinyloxiranes:  Synthesis of α,β-Epoxy-γ-butyrolactones

  摘要：

  Stereospecific beta-lithlation of beta-aryl-substituted oxazollnyloxiranes is described. The trapping reaction of such reactive intermediates with carbonyl compounds gave alpha,beta-epoxy-gamma-butyrolactones after deblocking of the oxazoline moiety. This methodology has been also extended to the synthesis of optically active alpha,beta-epoxy-gamma-butyrolactones.

  DOI：

  10.1021/ol025781i
• 作为产物：
  描述：

  苯甲醛 、 (4S)-2-chloromethyl-4-isopropyl-2-oxazoline 在 titanium(IV) isopropylate 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 以50%的产率得到(4S,2'S,3'R)-(-)-4-isopropyl-2-(3'-phenyloxiranyl)-4,5-dihydrooxazole
  参考文献：
  名称：

  Stereospecific β-Lithiation of Oxazolinyloxiranes:  Synthesis of α,β-Epoxy-γ-butyrolactones

  摘要：

  Stereospecific beta-lithlation of beta-aryl-substituted oxazollnyloxiranes is described. The trapping reaction of such reactive intermediates with carbonyl compounds gave alpha,beta-epoxy-gamma-butyrolactones after deblocking of the oxazoline moiety. This methodology has been also extended to the synthesis of optically active alpha,beta-epoxy-gamma-butyrolactones.

  DOI：

  10.1021/ol025781i

文献信息

• Lithiation of optically active oxazolinyloxiranes: configurational stability
  作者：Renzo Luisi、Vito Capriati、Claudia Carlucci、Leonardo Degennaro、Saverio Florio

  DOI：10.1016/j.tet.2003.09.018

  日期：2003.12

  The α-lithiation reaction of optically active oxazolinyloxiranes has been investigated. The trapping reaction with D2O, MeI and acetone affording substituted oxazolinyloxiranes proved that the corresponding lithiated species are configurationally unstable. A stereoconvergency was observed in the case of lithiation–deuteration sequence of two oxazolinyloxiranes.

  已经研究了光学活性的恶唑啉基氧杂环丁烷的α-锂化反应。用D 2 O，MeI和丙酮进行捕集反应，得到取代的恶唑啉基恶唑啉酮，证明相应的锂化物种构型不稳定。在两个恶唑啉基氧杂环丁烷的锂化-氘化序列的情况下，观察到立体会聚。
• Oxazolinyloxiranyllithium-mediated synthesis of highly strained heterocyclic compounds
  作者：Renzo Luisi、Vito Capriati、Leonardo Degennaro、Saverio Florio

  DOI：10.1016/j.tet.2003.09.017

  日期：2003.12

  The addition reaction of alpha-lithiated oxazolinyloxiranes to nitrones has been investigated. 1,5,9-Trioxa-8,10-diazadispiro[2.0.4.3]undecanes formed in a completely diastereoselective manner upon treatment of alpha-lithiated oxiranes with nitrones. The lithiation of optically active trans and cis-oxazolinyloxiranes followed by the addition of a nitrone resulted in the formation of the same dispirocyclic compound. An explanation for the observed stereoselectivity is provided. (C) 2003 Elsevier Ltd. All rights reserved.
• Stereospecific β-Lithiation of Oxazolinyloxiranes:  Synthesis of α,β-Epoxy-γ-butyrolactones
  作者：Vito Capriati、Leonardo Degennaro、Raffaele Favia、Saverio Florio、Renzo Luisi

  DOI：10.1021/ol025781i

  日期：2002.5.1

  Stereospecific beta-lithlation of beta-aryl-substituted oxazollnyloxiranes is described. The trapping reaction of such reactive intermediates with carbonyl compounds gave alpha,beta-epoxy-gamma-butyrolactones after deblocking of the oxazoline moiety. This methodology has been also extended to the synthesis of optically active alpha,beta-epoxy-gamma-butyrolactones.