(3S,6S,6aS)-6-Pent-4-enyl-3-phenyl-tetrahydro-1,5-dioxa-3a-aza-pentalen-4-one | 360776-18-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: (3S,6S,6aS)-6-Pent-4-enyl-3-phenyl-tetrahydro-1,5-dioxa-3a-aza-pentalen-4-one
• 英文别名: (3S,7S,7aS)-7-pent-4-enyl-3-phenyl-2,3,7,7a-tetrahydro-[1,3]oxazolo[3,2-c][1,3]oxazol-5-one
• CAS: 360776-18-7
• 化学式: C₁₆H₁₉NO₃
• 分子量: 273.332
• InChiKey: JADMPPMYPKJENH-ILXRZTDVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3S,6S,6aS)-6-Pent-4-enyl-3-phenyl-tetrahydro-1,5-dioxa-3a-aza-pentalen-4-one 在 Grubbs catalyst first generation 、 四氯化钛 作用下， 以 二氯甲烷 为溶剂， 生成 (Z)-3-((S)-2-Hydroxy-1-phenyl-ethyl)-3a,4,5,8,9,9a-hexahydro-3H-cyclooctaoxazol-2-one
  参考文献：
  名称：

  Ring-closing metathesis of diolefinic oxazolidinones: a new access to tropanes and aminocyclitols

  摘要：

  Ring-closing metathesis of diolefinic oxazolidinones prepared through N-Boc-2-acyl or alpha,beta -epoxy oxazolidine methodology give stereodefined bicyclic oxazolidinones. The 5,6-membered bicyclic oxazolidinones are then converted into new aminocyclitols by diastereoselective dihydroxylation whereas their 5,7-membered bicyclic homologues are transformed into tropanic alkaloids through an aminocyclization step. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)00830-9
• 作为产物：
  描述：

  magnesium,pent-1-ene,bromide 在 sodium tetrahydroborate 、 sodium hydride 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 生成 (3S,6S,6aS)-6-Pent-4-enyl-3-phenyl-tetrahydro-1,5-dioxa-3a-aza-pentalen-4-one
  参考文献：
  名称：

  Ring-closing metathesis of diolefinic oxazolidinones: a new access to tropanes and aminocyclitols

  摘要：

  Ring-closing metathesis of diolefinic oxazolidinones prepared through N-Boc-2-acyl or alpha,beta -epoxy oxazolidine methodology give stereodefined bicyclic oxazolidinones. The 5,6-membered bicyclic oxazolidinones are then converted into new aminocyclitols by diastereoselective dihydroxylation whereas their 5,7-membered bicyclic homologues are transformed into tropanic alkaloids through an aminocyclization step. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)00830-9