(5S,6S)-5,6-Di(benzoyloxy)-1-(2-bromoethyl)cyclohex-1-ene | 226255-51-2

• 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: (5S,6S)-5,6-Di(benzoyloxy)-1-(2-bromoethyl)cyclohex-1-ene
• 英文别名: [(1S,2R)-2-benzoyloxy-3-(2-bromoethyl)cyclohex-3-en-1-yl] benzoate
• CAS: 226255-51-2
• 化学式: C₂₂H₂₁BrO₄
• 分子量: 429.31
• InChiKey: LLJUFKUNVIJKJZ-VQTJNVASSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (5S,6S)-5,6-Di(benzoyloxy)-1-(2-bromoethyl)cyclohex-1-ene 在 咪唑 、 lithium hydroxide 、 sodium tetrahydroborate 、 1,1,2,3-四甲基胍 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 (7R,8S,10bS)-8-(tert-Butyl-dimethyl-silanyloxy)-7-hydroxy-1,5,6,7,8,9,10,10b-octahydro-oxazolo[4,3-a]isoquinolin-3-one
  参考文献：
  名称：

  Model Study for a General Approach to Morphine and Noroxymorphone via a Rare Heck Cyclization

  摘要：

  [GRAPHICS]beta-Bromoethylbenzene was converted to the pentacycle 6 in 11 steps. The key features of this model were the toluene dioxygenase catalyzed production of diol 13 and the stereospecific Heck closure of 5 to 6.

  DOI：

  10.1021/ol991135g
• 作为产物：
  描述：

  2-(2-Bromoethyl)cyclohexa-1,3-diene 在 4-二甲氨基吡啶 、 溶剂黄146 、 N,N'-二环己基碳二亚胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 (5S,6S)-5,6-Di(benzoyloxy)-1-(2-bromoethyl)cyclohex-1-ene
  参考文献：
  名称：

  Model Study for a General Approach to Morphine and Noroxymorphone via a Rare Heck Cyclization

  摘要：

  [GRAPHICS]beta-Bromoethylbenzene was converted to the pentacycle 6 in 11 steps. The key features of this model were the toluene dioxygenase catalyzed production of diol 13 and the stereospecific Heck closure of 5 to 6.

  DOI：

  10.1021/ol991135g

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.
• Model Study for a General Approach to Morphine and Noroxymorphone via a Rare Heck Cyclization
  作者：Dean A. Frey、Caiming Duan、Tomas Hudlicky

  DOI：10.1021/ol991135g

  日期：1999.12.1

  [GRAPHICS]beta-Bromoethylbenzene was converted to the pentacycle 6 in 11 steps. The key features of this model were the toluene dioxygenase catalyzed production of diol 13 and the stereospecific Heck closure of 5 to 6.