(2S,3S,8S,9S,10S)-2,3-diphenyl-8-phenylselenenyloctahydrobenzo-1,4-oxazine | 405144-79-8

• 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,8S,9S,10S)-2,3-diphenyl-8-phenylselenenyloctahydrobenzo-1,4-oxazine
• 英文别名: (2S,3S,4aS,8S,8aS)-2,3-diphenyl-8-phenylselanyl-3,4,4a,5,6,7,8,8a-octahydro-2H-benzo[b][1,4]oxazine
• CAS: 405144-79-8
• 化学式: C₂₆H₂₇NOSe
• 分子量: 448.466
• InChiKey: IWLBBTBJNZSXPP-LROMGURASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.83
• 重原子数：
  29
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  21.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2S,3S,8S,9S,10S)-2,3-diphenyl-8-phenylselenenyloctahydrobenzo-1,4-oxazine 在 sodium periodate 、 sodium hydride 、 碳酸氢钠 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 49.5h， 生成 (2S,3S,9R,10S)-4-benzyloxycarbonyl-2,3-diphenyl-2,3;5,6;9,10-hexahydrobenzo-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
• 作为产物：
  描述：

  3-溴环己烯 在 四(三苯基膦)钯 三乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 8.0h， 生成 (2S,3S,8S,9S,10S)-2,3-diphenyl-8-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

文献信息

• Introduction of cis-vicinal amino alcohol functionality into the cyclohexane ring employing (1S,2S)-2-amino-1,2-diphenylethanol: synthesis of enantiopure aminocyclohexitols
  作者：Kwan Soo Kim、Sung Ook Choi、Jong Myun Park、Yong Joo Lee、Jin Hwan Kim

  DOI：10.1016/s0957-4166(01)00484-0

  日期：2001.10

  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.