(S)-4-methoxymethyl-2-phenyl-oxazoline | 148278-93-7

• 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: (S)-4-methoxymethyl-2-phenyl-oxazoline
• 英文别名: (4S)-4-(methoxymethyl)-2-phenyl-4,5-dihydro-1,3-oxazole
• CAS: 148278-93-7
• 化学式: C₁₁H₁₃NO₂
• 分子量: 191.23
• InChiKey: QPNSEMBLSMYWAM-JTQLQIEISA-N

物化性质

• 沸点：
  292.3±13.0 °C(Predicted)
• 密度：
  1.12±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  30.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-4-methoxymethyl-2-phenyl-oxazoline 在 盐酸 作用下， 以 水 为溶剂， 生成 (R)-2-氨基-3-甲氧基丙-1-醇
  参考文献：
  名称：

  Concise synthesis of (+)-serinolamide A

  摘要：

  Serinolamide A, isolated from a species of marine cyanobacteria, exhibits a moderate agonist effect and selectivity for the CB1 cannabinoid receptor, which is unusual for marine natural products. Herein, we reported a highly efficient enantiospecific first total synthesis of (+)-serinolamide A from L-serine in nine steps with 30% overall yield. The synthesis method provides a facile, practicable, and economical approach for the preparation of other similar endocanabinoid lipids. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.09.084
• 作为产物：
  描述：

  苯甲亚胺酸乙酯 在 sodium hydride 、 二异丁基氢化铝 作用下， 以 甲醇 为溶剂， 生成 (S)-4-methoxymethyl-2-phenyl-oxazoline
  参考文献：
  名称：

  Concise synthesis of (+)-serinolamide A

  摘要：

  Serinolamide A, isolated from a species of marine cyanobacteria, exhibits a moderate agonist effect and selectivity for the CB1 cannabinoid receptor, which is unusual for marine natural products. Herein, we reported a highly efficient enantiospecific first total synthesis of (+)-serinolamide A from L-serine in nine steps with 30% overall yield. The synthesis method provides a facile, practicable, and economical approach for the preparation of other similar endocanabinoid lipids. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.09.084

文献信息

• Asymmetric Addition to Chiral Aromatic and Unsaturated Oxazolines Using a Novel Chiral Auxiliary
  作者：A. I. Meyers、Wolfgang Schmidt、Marc J. Mckennon

  DOI：10.1055/s-1993-25842

  日期：——

  By utilizing S-serine, both enantiomers of the reduced methoxyamino alcohol (12) were efficiently prepared. The corresponding oxazolines, prepared from these auxiliaries, showed favorable properties toward additions to naphthalenes 22 and cyclohexene, 27.

  通过利用S-丝氨酸，成功合成了还原的甲氧基氨醇（12）的两种对映体。由这些辅助试剂制备的相应噁唑啉在与萘（22）和环己烯（27）的加成反应中显示出良好的性能。
• Concise synthesis of (+)-serinolamide A
  作者：Ya-Ru Gao、Shi-Huan Guo、Zhuan-Xiang Zhang、Shuai Mao、Yan-Lei Zhang、Yong-Qiang Wang

  DOI：10.1016/j.tetlet.2013.09.084

  日期：2013.11

  Serinolamide A, isolated from a species of marine cyanobacteria, exhibits a moderate agonist effect and selectivity for the CB1 cannabinoid receptor, which is unusual for marine natural products. Herein, we reported a highly efficient enantiospecific first total synthesis of (+)-serinolamide A from L-serine in nine steps with 30% overall yield. The synthesis method provides a facile, practicable, and economical approach for the preparation of other similar endocanabinoid lipids. (C) 2013 Elsevier Ltd. All rights reserved.