[(1S,2R)-2-benzoyloxy-3-[2-(4-hydroxy-2-oxo-1,3-oxazolidin-3-yl)ethyl]cyclohex-3-en-1-yl] benzoate

• 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: [(1S,2R)-2-benzoyloxy-3-[2-(4-hydroxy-2-oxo-1,3-oxazolidin-3-yl)ethyl]cyclohex-3-en-1-yl] benzoate
• 化学式: C₂₅H₂₅NO₇
• 分子量: 451.476
• InChiKey: FOWLFDYVHTVZLW-JAFNVKOHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  33
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  102
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  [(1S,2R)-2-benzoyloxy-3-[2-(4-hydroxy-2-oxo-1,3-oxazolidin-3-yl)ethyl]cyclohex-3-en-1-yl] benzoate 在 lithium hydroxide 、 四氯化钛 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 甲醇 、 二氯甲烷 、 二甲基亚砜 为溶剂， 生成 (7S,8R,10bR)-7,8-Dihydroxy-1,5,6,7,8,9,10,10b-octahydro-oxazolo[4,3-a]isoquinolin-3-one
  参考文献：
  名称：

  Chemoenzymatic and electrochemical oxidations in the synthesis of octahydroisoquinolines for conversion to morphine. Relative merits of radical vs. acid-catalyzed cyclizations

  摘要：

  Second-generation stereoselective synthesis of octahydroisoquinoline 3, a potential key intermediate for the projected synthesis of the natural enantiomer of morphine, has been accomplished in five steps from arene cis-diol 8. Electrochemical oxidation of 9b furnished 7b, a precursor for the key benzoate-assisted acyl-iminium cyclization. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)10384-7
• 作为产物：
  描述：

  (1R,2S)-3-(2-Bromo-ethyl)-cyclohex-3-ene-1,2-diol 在 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 1,1,2,3-四甲基胍 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 生成 [(1S,2R)-2-benzoyloxy-3-[2-(4-hydroxy-2-oxo-1,3-oxazolidin-3-yl)ethyl]cyclohex-3-en-1-yl] benzoate
  参考文献：
  名称：

  Chemoenzymatic and electrochemical oxidations in the synthesis of octahydroisoquinolines for conversion to morphine. Relative merits of radical vs. acid-catalyzed cyclizations

  摘要：

  Second-generation stereoselective synthesis of octahydroisoquinoline 3, a potential key intermediate for the projected synthesis of the natural enantiomer of morphine, has been accomplished in five steps from arene cis-diol 8. Electrochemical oxidation of 9b furnished 7b, a precursor for the key benzoate-assisted acyl-iminium cyclization. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)10384-7

文献信息

• Intramolecular N-Acyliminium Ion-Olefin Cyclization in the Synthesis of Optically Pure Isoquinoline Derivatives: Control of Stereochemistry and Application to Synthesis of Morphine Alkaloids
  作者：Patricia Bottari、Mary Ann A. Endoma、Tomáš Hudlický、Ion Ghiviriga、Khalil A. Abboud

  DOI：10.1135/cccc19990203

  日期：——

  The 3-[2-(cyclohex-1-eneyl)ethyl]-[1,3]oxazoline-2,4-dione derivatives 9, 14 and 16 were subjected to hydride reduction followed by acid-catalyzed olefin-N-acyliminium ion cyclization to afford a series of perhydroisoquinolines 10, 11a, 11b, 19a-19c, 20a, 20b and 21. A mechanism was proposed that accounts for the observed stereoselectivity of the cyclization reactions based on the neighboring group participation by a benzoate group.

  3-[2-(环己-1-烯基)乙基]-[1,3]噁唑-2,4-二酮衍生物9、14和16经过氢化还原后，接着进行酸催化的烯烃-N-酰亚胺离子环化反应，得到一系列的过氢化异喹啉10、11a、11b、19a-19c、20a、20b和21。提出了一种机理，解释了邻基参与的苯甲酸酯基对环化反应的立体选择性。
• Chemoenzymatic and electrochemical oxidations in the synthesis of octahydroisoquinolines for conversion to morphine. Relative merits of radical vs. acid-catalyzed cyclizations
  作者：Mary Ann Endoma、Gabor Butora、Christopher D. Claeboe、Tomas Hudlicky、Khalil A. Abboud

  DOI：10.1016/s0040-4039(97)10384-7

  日期：1997.12

  Second-generation stereoselective synthesis of octahydroisoquinoline 3, a potential key intermediate for the projected synthesis of the natural enantiomer of morphine, has been accomplished in five steps from arene cis-diol 8. Electrochemical oxidation of 9b furnished 7b, a precursor for the key benzoate-assisted acyl-iminium cyclization. (C) 1997 Elsevier Science Ltd.