2-Phenyl-4(S)-(2(S)-hydroxypent-4-enyl)-2-oxazoline | 130459-39-1

• 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(S)-hydroxypent-4-enyl)-2-oxazoline
• 英文别名: (2S)-1-[(4S)-2-phenyl-4,5-dihydro-1,3-oxazol-4-yl]pent-4-en-2-ol
• CAS: 130459-39-1
• 化学式: C₁₄H₁₇NO₂
• 分子量: 231.294
• InChiKey: ANCUFHVEGSXAPZ-STQMWFEESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 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：

  2-Phenyl-4(S)-(2(S)-hydroxypent-4-enyl)-2-oxazoline 在 二异丁基氢化铝 、 三乙胺 作用下， 以 正己烷 、 二氯甲烷 、 甲苯 为溶剂， 反应 0.16h， 生成 (2S,4'S)-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：

  烯丙基三丁基锡 、 (4S)-4-(2'-Oxoethyl)-2-phenyloxazoline 在 正丁基锂 、 三甲基铝 作用下， 以 乙醚 、 正己烷 为溶剂， 以59%的产率得到2-Phenyl-4(S)-(2(R)-hydroxypent-4-enyl)-2-oxazoline
  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

文献信息

• Studies toward the application of oxazolineepoxide equivalency in 1,3-asymmetric induction
  作者：Kenneth R. Overly、J.Michael Willams、Glenn J. McGarvey

  DOI：10.1016/s0040-4039(00)97679-2

  日期：1990.1
• 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.
• OVERLY, KENNETH R.;WILLIAMS, J. MICHAEL;MCGARVEY, GLENN J., TETRAHEDRON LETT., 31,(1990) N2, C. 4573-4576
  作者：OVERLY, KENNETH R.、WILLIAMS, J. MICHAEL、MCGARVEY, GLENN J.

  DOI：——

  日期：——