(2S,3S,7R,8R,9S,10S)-4-benzyloxycarbonyl-8-hydroxy-2,3-diphenyl-7-phenylselenenyloctahydrobenzo-1,4-oxazine | 405144-83-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (2S,3S,7R,8R,9S,10S)-4-benzyloxycarbonyl-8-hydroxy-2,3-diphenyl-7-phenylselenenyloctahydrobenzo-1,4-oxazine
• 英文别名: benzyl (2S,3S,4aS,7R,8R,8aS)-8-hydroxy-2,3-diphenyl-7-phenylselanyl-2,3,4a,5,6,7,8,8a-octahydrobenzo[b][1,4]oxazine-4-carboxylate
• CAS: 405144-83-4
• 化学式: C₃₄H₃₃NO₄Se
• 分子量: 598.6
• InChiKey: IOGAWASFTZTEDP-ACQYNFKHSA-N

物化性质

• 沸点：
  721.9±60.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.85
• 重原子数：
  40
• 可旋转键数：
  7
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  59
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2S,3S,7R,8R,9S,10S)-4-benzyloxycarbonyl-8-hydroxy-2,3-diphenyl-7-phenylselenenyloctahydrobenzo-1,4-oxazine 在 sodium periodate 、 iodonium(di-γ-collidine) perchlorate 、 sodium hydride 、 碳酸氢钠 作用下， 以 四氢呋喃 、 甲醇 、 氯仿 、 水 为溶剂， 反应 70.0h， 生成 (4R,7S,8S,10S,11R,12S,13S)-6-benzyloxycarbonyl-4-iodo-3-methyl-2-oxo-7,8-diphenyldecahydro-1,9-dioxa-3,6-diazacyclopenta[a]naphthalene
  参考文献：
  名称：

  Introduction of cis-vicinal amino alcohol functionality into the cyclohexane ring employing (1S,2S)-2-amino-1,2-diphenylethanol: synthesis of enantiopure aminocyclohexitols

  摘要：

  Pd(0)-catalyzed allylic amination of 3-bromocyclohexene with (1S,2S)-2-amino-1,2-diphenylethanol and subsequent intramolecular oxyselenenylation of the resulting allylic amine 6 followed by oxidation-elimination afforded the valuable cis-fused bicyclic olefin 10. Oxyselenenylation of cyclohexene with (1S,2S)-N-(benzyloxycarbonyl)-2-amino-1,2-diphenylethanol and subsequent oxidation-elimination gave the allylic ether 18. Intramolecular aminoselenenylation of 18 followed by oxidation elimination provided the cis-fused bicyclic olefin 21, which is the regioisomer of 10. Further stereoselective transformation of 10 afforded enantiopure aminocyclohexitols. (C) 2001 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(01)00484-0
• 作为产物：
  描述：

  3-溴环己烯 在 四(三苯基膦)钯 sodium tetrahydroborate 、 sodium periodate 、 二甲基二环氧乙烷 、 sodium hydride 、 碳酸氢钠 、 三乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 63.0h， 生成 (2S,3S,7R,8R,9S,10S)-4-benzyloxycarbonyl-8-hydroxy-2,3-diphenyl-7-phenylselenenyloctahydrobenzo-1,4-oxazine
  参考文献：
  名称：

  Introduction of cis-vicinal amino alcohol functionality into the cyclohexane ring employing (1S,2S)-2-amino-1,2-diphenylethanol: synthesis of enantiopure aminocyclohexitols

  摘要：

  Pd(0)-catalyzed allylic amination of 3-bromocyclohexene with (1S,2S)-2-amino-1,2-diphenylethanol and subsequent intramolecular oxyselenenylation of the resulting allylic amine 6 followed by oxidation-elimination afforded the valuable cis-fused bicyclic olefin 10. Oxyselenenylation of cyclohexene with (1S,2S)-N-(benzyloxycarbonyl)-2-amino-1,2-diphenylethanol and subsequent oxidation-elimination gave the allylic ether 18. Intramolecular aminoselenenylation of 18 followed by oxidation elimination provided the cis-fused bicyclic olefin 21, which is the regioisomer of 10. Further stereoselective transformation of 10 afforded enantiopure aminocyclohexitols. (C) 2001 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(01)00484-0