2-phenyl-4(S)-<2-((2-methyl-2-propyl)thio)-2-oxoethyl>-2-oxazoline | 102614-13-1

• 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: 2-phenyl-4(S)-<2-((2-methyl-2-propyl)thio)-2-oxoethyl>-2-oxazoline
• 英文别名: 2-phenyl-4(S)-{2-[(2-methyl-2-propyl)thio]-2-oxoethyl}-2-oxazoline；S-tert-butyl 2-[(4S)-2-phenyl-4,5-dihydro-1,3-oxazol-4-yl]ethanethioate
• CAS: 102614-13-1
• 化学式: C₁₅H₁₉NO₂S
• 分子量: 277.387
• InChiKey: GLMXAFHXMUPJJM-LBPRGKRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  64
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-phenyl-4(S)-<2-((2-methyl-2-propyl)thio)-2-oxoethyl>-2-oxazoline 在 二异丁基氢化铝 、 三乙胺 、 zinc(II) chloride 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 、 二氯甲烷 、 甲苯 为溶剂， 反应 3.24h， 生成 (2S,4R)-2-(N-Benzylamino)-4-<oxy>-6-hepten-1-ol
  参考文献：
  名称：

  Synthetic Studies on the Polyene Macrolide Antibiotics. Development of syn- and anti-1,3-Diol Subunits and Assembly of the Polyacetate Region of Amphotericin B

  摘要：

  The synthesis of syn- and anti-1,3-diol subunits from thiol ester oxazoline 4 has been described. The key features of these synthetic sequences include the stereodivergent allylation of an asymmetric beta-amino aldehyde (7) and the stereospecific transformation of a vicinal amino alcohol to an epoxide. The resultant diasteromeric silyl-protected epoxy alcohols (10s and 10a) serve as convenient precursors to the isomeric diol aldehyde derivatives 13, 13-ent, and 16. One of these fragments, compound 13, has been exploited in a highly convergent synthesis of the C1-C13 polyacetate segment of amphotericin B.

  DOI：

  10.1021/jo00129a019
• 作为产物：
  描述：

  苯甲酰氯 、 alkaline earth salt of/the/ methylsulfuric acid 在 三乙胺 作用下， 以 吡啶 、 二氯甲烷 为溶剂， 反应 60.0h， 生成 2-phenyl-4(S)-<2-((2-methyl-2-propyl)thio)-2-oxoethyl>-2-oxazoline
  参考文献：
  名称：

  L-天冬氨酸在无环立体选择性合成中。两性霉素B的合成研究

  摘要：

  合成这些片段 C21-C37 de l'amphotericine B, l t-丁基二甲基甲硅烷氧基-15 二甲基-14,16 甲氧基乙氧基甲氧基-17 十八碳烯-2,4,6,8,10,12 al

  DOI：

  10.1021/ja00276a040

文献信息

• 2-phenyloxazolines as carboxylate precursors - applications to the synthesis of asymmetric branched-chain structures
  作者：Glenn J. McGarvey、Kenneth J. Wilson、Carl E. Shanholtz

  DOI：10.1016/s0040-4039(00)79046-0

  日期：1992.5

  A synthetic approach to the title compounds is presented that features the asymmetric elaboration of a chiral, non-racemic oxazoline followed by a two-step oxidative ring cleavage of the heterocycle to a triamide for further transformation.
• The asymmetric synthesis of branched chain polyketide compounds through stereoselective aldol condensations of .beta.-heteroatom ester enolates
  作者：Glenn J. McGarvey、Roger N. Hiner、J. Michael Williams、Yoshio Matsubara、James W. Poarch

  DOI：10.1021/jo00369a047

  日期：1986.9
• A remarkable base-induced rearrangement of hydroxy oxazolines to amido tetrahydrofurans
  作者：Kenneth J. Wilson、Michal Sabat、Glenn J. McGarvey

  DOI：10.1021/jo00075a007

  日期：1993.11

  Asymmetric beta-hydroxy oxazolines have been shown to rearrange at room temperature to isomeric tetrahydrofurans when deprotonated with potassium hydride in tetrahydrofuran.
• Synthetic Studies on the Polyene Macrolide Antibiotics. Development of syn- and anti-1,3-Diol Subunits and Assembly of the Polyacetate Region of Amphotericin B
  作者：Glenn J. McGarvey、Jeffrey A. Mathys、Kenneth J. Wilson、Kenneth R. Overly、Paul T. Buonora、P. Grant Spoors

  DOI：10.1021/jo00129a019

  日期：1995.12

  The synthesis of syn- and anti-1,3-diol subunits from thiol ester oxazoline 4 has been described. The key features of these synthetic sequences include the stereodivergent allylation of an asymmetric beta-amino aldehyde (7) and the stereospecific transformation of a vicinal amino alcohol to an epoxide. The resultant diasteromeric silyl-protected epoxy alcohols (10s and 10a) serve as convenient precursors to the isomeric diol aldehyde derivatives 13, 13-ent, and 16. One of these fragments, compound 13, has been exploited in a highly convergent synthesis of the C1-C13 polyacetate segment of amphotericin B.
• L-Aspartic acid in acyclic stereoselective synthesis. Synthetic studies on amphotericin B
  作者：Glenn J. McGarvey、J. Michael. Williams、Roger N. Hiner、Yoshio. Matsubara、Taeboem. Oh

  DOI：10.1021/ja00276a040

  日期：1986.8

  Synthese du fragment C21-C37 de l'amphotericine B, le t-butyldimethylsiloxy-15 dimethyl-14,16 methoxyethoxymethoxy-17 octadecaene-2,4,6,8,10,12 al

  合成这些片段 C21-C37 de l'amphotericine B, l t-丁基二甲基甲硅烷氧基-15 二甲基-14,16 甲氧基乙氧基甲氧基-17 十八碳烯-2,4,6,8,10,12 al