(3'R,1S,2R)-N-(4'-benzyloxycarbonylphenyl)-4',4'-dimethyl-2'-oxopyrrolidin-3'-yl 2-(benzyloxycarbonylamino)cyclohex-3-ene-1-carboxylate | 862248-97-3

• 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: (3'R,1S,2R)-N-(4'-benzyloxycarbonylphenyl)-4',4'-dimethyl-2'-oxopyrrolidin-3'-yl 2-(benzyloxycarbonylamino)cyclohex-3-ene-1-carboxylate
• 英文别名: benzyl 4-[(3R)-4,4-dimethyl-2-oxo-3-[(1S,2R)-2-(phenylmethoxycarbonylamino)cyclohex-3-ene-1-carbonyl]oxypyrrolidin-1-yl]benzoate
• CAS: 862248-97-3
• 化学式: C₃₅H₃₆N₂O₇
• 分子量: 596.68
• InChiKey: TWUGBEGHXLJMOP-JBOQNHBVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  44
• 可旋转键数：
  12
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  111
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (3'R,1S,2R)-N-(4'-benzyloxycarbonylphenyl)-4',4'-dimethyl-2'-oxopyrrolidin-3'-yl 2-(benzyloxycarbonylamino)cyclohex-3-ene-1-carboxylate 在 lithium hydroxide 、 2-氯-1-甲基吡啶碘化物 、 水 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 5.0h， 生成 (1S,2R)-1-benzylcarbamoyl-2-(benzyloxycarbonylamino)cyclohex-3-ene
  参考文献：
  名称：

  (R)-(4-(Benzyloxycarbonylphenyl)-3-hydroxy-4,4-dimethyl-2-pyrrolidinone) acrylate derivative as a chiral dienophile for the synthesis of enantiopure 2-aminocyclohexane carboxylic acids

  摘要：

  An asymmetric Diels-Alder reaction between the enantiopure (R)-benzyl-4-(3-acryloyloxy-4,4-dimethyl-2-oxopyrrolidin-1-yl)-benzoate (R)-2 and the N-Z-aminodiene 3 proceeded with total endo diastereoselectivity and was facially controlled in favour of the (3'R,1R,2S)-adduct. The two adducts obtained, 4 (the main compound) and 5, were isolated pure after Column chromatography on silica gel. Their LiOH hydrolysis followed by palladium-catalyzed hydrogenation of the double bond concomitant with hydrogenolysis of the carbamate moiety yielded the enantiopure cis-2-aminocyclohexane carboxylic acids (1R,2S)-8 and (1S,2R)-8. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.05.024
• 作为产物：
  描述：

  (R)-benzyl 4-(3-acryloyloxy-4,4-dimethyl-2-oxopyrrolidin-1-yl)-benzoate 、 (1e)-1,3-丁二烯氨基甲酸苄酯 以 甲苯 为溶剂， 反应 24.0h， 以46%的产率得到(3'R,1R,2S)-N-(4'-benzyloxycarbonylphenyl)-4',4'-dimethyl-2'-oxopyrrolidin-3'-yl 2-(benzyloxycarbonylamino)cyclohex-3-ene-1-carboxylate
  参考文献：
  名称：

  (R)-(4-(Benzyloxycarbonylphenyl)-3-hydroxy-4,4-dimethyl-2-pyrrolidinone) acrylate derivative as a chiral dienophile for the synthesis of enantiopure 2-aminocyclohexane carboxylic acids

  摘要：

  An asymmetric Diels-Alder reaction between the enantiopure (R)-benzyl-4-(3-acryloyloxy-4,4-dimethyl-2-oxopyrrolidin-1-yl)-benzoate (R)-2 and the N-Z-aminodiene 3 proceeded with total endo diastereoselectivity and was facially controlled in favour of the (3'R,1R,2S)-adduct. The two adducts obtained, 4 (the main compound) and 5, were isolated pure after Column chromatography on silica gel. Their LiOH hydrolysis followed by palladium-catalyzed hydrogenation of the double bond concomitant with hydrogenolysis of the carbamate moiety yielded the enantiopure cis-2-aminocyclohexane carboxylic acids (1R,2S)-8 and (1S,2R)-8. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.05.024