5-[4-(4,4-dimethyl-4,5-dihydro-1,3-oxazol-2-yl)-3-methylisoxazol-5-yl]pent-1-en-3-ol | 1029133-06-9

• 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: 5-[4-(4,4-dimethyl-4,5-dihydro-1,3-oxazol-2-yl)-3-methylisoxazol-5-yl]pent-1-en-3-ol
• 英文别名: 5-[4-(4,4-dimethyl-5H-1,3-oxazol-2-yl)-3-methyl-1,2-oxazol-5-yl]pent-1-en-3-ol
• CAS: 1029133-06-9
• 化学式: C₁₄H₂₀N₂O₃
• 分子量: 264.324
• InChiKey: DJMHYPGVCFUIBP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  67.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  环氧丁烯 、 4-(4',5'-dihydro-4',4'-dimethyl-Δ²-oxazolin-2-yl)-3,5-dimethylisoxazole 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 2.0h， 以28%的产率得到2-{[4-(4,4-dimethyl-4,5-dihydro-1,3-oxazol-2-yl)-3-methylisoxazol-5-yl]methyl}but-3-en-1-ol
  参考文献：
  名称：

  Synthetic utility of epoxides for chiral functionalization of isoxazoles

  摘要：

  The lithio-anion of isoxazole 2 was found to ring open propylene oxide in good yields with complete regioselectivity. Vinylic and benzylic epoxides were utilized as key examples of electrophiles and found to produce a mixture of regioisomeric adducts. Additionally, the use of chiral epoxides was explored, and absolute configuration was determined by X-ray crystallography to prove that nucleophilic attack at the benzylic carbon of (R)-styrene oxide proceeds with 100% inversion at the benzylic carbon to afford the (S)-alcohol (4b). (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.03.059

文献信息

• Synthetic utility of epoxides for chiral functionalization of isoxazoles
  作者：Jared K. Nelson、Christopher T. Burns、Miles P. Smith、Brendan Twamley、N.R. Natale

  DOI：10.1016/j.tetlet.2008.03.059

  日期：2008.5

  The lithio-anion of isoxazole 2 was found to ring open propylene oxide in good yields with complete regioselectivity. Vinylic and benzylic epoxides were utilized as key examples of electrophiles and found to produce a mixture of regioisomeric adducts. Additionally, the use of chiral epoxides was explored, and absolute configuration was determined by X-ray crystallography to prove that nucleophilic attack at the benzylic carbon of (R)-styrene oxide proceeds with 100% inversion at the benzylic carbon to afford the (S)-alcohol (4b). (C) 2008 Elsevier Ltd. All rights reserved.