(1S,3S,4R)-2-Benzyl-2-aza-bicyclo[2.2.1]hept-5-ene-3-carboxylic acid (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester | 379685-59-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (1S,3S,4R)-2-Benzyl-2-aza-bicyclo[2.2.1]hept-5-ene-3-carboxylic acid (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester
• 英文别名: [(1R,2S,5R)-5-methyl-2-propan-2-ylcyclohexyl] (1S,3S,4R)-2-benzyl-2-azabicyclo[2.2.1]hept-5-ene-3-carboxylate
• CAS: 379685-59-3
• 化学式: C₂₄H₃₃NO₂
• 分子量: 367.532
• InChiKey: WFXPKNGNILIJOZ-RRWKQDFOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1S,3S,4R)-2-Benzyl-2-aza-bicyclo[2.2.1]hept-5-ene-3-carboxylic acid (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester 在 lithium aluminium tetrahydride 作用下， 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：

  (1R)-(-)-薄荷基乙醛酸 在 3 A molecular sieve 、 三氟化硼乙醚 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 5.5h， 生成 (1S,3S,4R)-2-Benzyl-2-aza-bicyclo[2.2.1]hept-5-ene-3-carboxylic acid (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester
  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

文献信息

• 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.