2-[(E)-Benzylimino]-1-((1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-ethanone | 471242-92-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 2-[(E)-Benzylimino]-1-((1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-ethanone
• 英文别名: 2-benzylimino-1-[(1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3lambda6-thia-4-azatricyclo[5.2.1.01,5]decan-4-yl]ethanone；2-benzylimino-1-[(1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3λ6-thia-4-azatricyclo[5.2.1.01,5]decan-4-yl]ethanone
• CAS: 471242-92-9
• 化学式: C₁₉H₂₄N₂O₃S
• 分子量: 360.477
• InChiKey: CXFIXJXDOTYAPK-GPMSIDNRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  75.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-[(E)-Benzylimino]-1-((1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-ethanone 在 lithium aluminium tetrahydride 、 三氟化硼乙醚 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 5.5h， 生成 (-)-[(1S,3-exo)-2-benzyl-2-azabicyclo[2.2.1]hept-5-en-3-yl]methanol
  参考文献：
  名称：

  Diastereoselectivity in the hetero [4+2] cycloaddition of cyclopentadiene to N-benzyliminoacetyl derivatives of (2R)-bornane-10,2-sultam and other chiral secondary alcohols

  摘要：

  Various protonated chiral glyoxyloyl-alpha -imino-N-benzyl hetero-dienophiles have been examined in the diastereoselective exo-cycloaddition to cyclopentadiene at -78 degreesC promoted by CF3CO2-BF3, a dissociated non-nucleophilic counter ion. The best pi -facial selectivities were observed with (2R)-bornane-10,2-sultam (76% d.e.) and (2R)-10-dicyclohexylsulfonamoyl-isoborneol (80% d.e.) as chiral auxiliaries. These conditions were found to be superior in terms of yields and selectivities as compared to analogous aza-dienophiles treated with simple Lewis acids or under thermal conditions. Absolute configurations were assigned on the basis of an X-ray analysis of the major cycloadduct (3 'S)-3a as well as by chiroptical comparison with the corresponding new amino alcohol (-)-(3S)-4a. Plausible transition states are briefly discussed on the basis of PM3 conformational calculations. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00356-1
• 作为产物：
  描述：

  (3aS,6R,7aR)-hexahydro-1-<(ζ)-(hydroxy)(methoxy)acetyl>-8,8-dimethyl-3H-3a,6-methano-2,1-benzisothiazole 2,2-dioxide 、 苄胺 在 sodium sulfate 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 生成 2-[(E)-Benzylimino]-1-((1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-ethanone
  参考文献：
  名称：

  Lee, Jung Gyu; Choi, Kyung Il; Pae, Ae Nim, Journal of the Chemical Society. Perkin Transactions 1 (2001), 2002, # 10, p. 1314 - 1317

  摘要：

  DOI：

文献信息

• Lee, Jung Gyu; Choi, Kyung Il; Pae, Ae Nim, Journal of the Chemical Society. Perkin Transactions 1 (2001), 2002, # 10, p. 1314 - 1317
  作者：Lee, Jung Gyu、Choi, Kyung Il、Pae, Ae Nim、Koh, Hun Yeong、Kang, Yonghan、Cho, Yong Seo

  DOI：——

  日期：——
• Diastereoselectivity in the hetero [4+2] cycloaddition of cyclopentadiene to N-benzyliminoacetyl derivatives of (2R)-bornane-10,2-sultam and other chiral secondary alcohols
  作者：Sławomir Szymański、Christian Chapuis、Janusz Jurczak

  DOI：10.1016/s0957-4166(01)00356-1

  日期：2001.7

  Various protonated chiral glyoxyloyl-alpha -imino-N-benzyl hetero-dienophiles have been examined in the diastereoselective exo-cycloaddition to cyclopentadiene at -78 degreesC promoted by CF3CO2-BF3, a dissociated non-nucleophilic counter ion. The best pi -facial selectivities were observed with (2R)-bornane-10,2-sultam (76% d.e.) and (2R)-10-dicyclohexylsulfonamoyl-isoborneol (80% d.e.) as chiral auxiliaries. These conditions were found to be superior in terms of yields and selectivities as compared to analogous aza-dienophiles treated with simple Lewis acids or under thermal conditions. Absolute configurations were assigned on the basis of an X-ray analysis of the major cycloadduct (3 'S)-3a as well as by chiroptical comparison with the corresponding new amino alcohol (-)-(3S)-4a. Plausible transition states are briefly discussed on the basis of PM3 conformational calculations. (C) 2001 Elsevier Science Ltd. All rights reserved.