tert-butyl (2S)-1-[(1E)-buta-1,3-dienyl]-5-oxopyrrolidine-2-carboxylate | 175789-22-7

• 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: tert-butyl (2S)-1-[(1E)-buta-1,3-dienyl]-5-oxopyrrolidine-2-carboxylate
• CAS: 175789-22-7
• 化学式: C₁₃H₁₉NO₃
• 分子量: 237.299
• InChiKey: JYIGZTCIRGNZSS-ZKXNXJMVSA-N

物化性质

• 沸点：
  358.1±31.0 °C(Predicted)
• 密度：
  1.124±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-羟基氨基甲酸叔丁酯 、 tert-butyl (2S)-1-[(1E)-buta-1,3-dienyl]-5-oxopyrrolidine-2-carboxylate 在 benzyltrimethylammonium periodate 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以72%的产率得到t-butyl (6S)-6-[(5'S)-5'-t-butyloxycarbonyl-2'-oxo-pyrrolidin-1'-yl]-3,6-dihydro-2H-1,2-oxazine-2-carboxylate
  参考文献：
  名称：

  Asymmetric synthesis of potent glycosidase and very potent α-mannosidase inhibitors: 4-amino-4-deoxy-l-erythrose and 4-amino-4,5-dideoxy-l-ribose

  摘要：

  Pyrrolidine amino-sugars, cyclic iminoalditols as well as linear aminoalditols in 4-amino-L-erythrose and 4-amino-5-deoxy-L-ribose series were synthesised by asymmetric hetero-Diels-Alder reaction followed by chemical transformations. 4-Amino-4-deoxy-L-erythrose and 4-amino-4,5-dideoxy-L-ribose were potent beta-D-glucosidase, alpha-D-mannosidase, alpha- and beta-D-galactosidase inhibitors. We have shown that the ribose derivative was a very potent inhibitor of alpha-D-mannosidase. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)01512-0
• 作为产物：
  描述：

  醋酸叔丁酯 在 高氯酸 、 4 A molecular sieve 、 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 反应 8.0h， 生成 tert-butyl (2S)-1-[(1E)-buta-1,3-dienyl]-5-oxopyrrolidine-2-carboxylate
  参考文献：
  名称：

  酰基亚硝基二烯基不对称杂Diels-Alder反应中的手性N-二烯基-L-焦谷氨酸酯

  摘要：

  的N二烯基- L-焦酯的不对称狄尔斯-阿尔德反应1A-H与酰基亚硝基亲二烯体4A-H ，得到非对映体加合物6A-n中，图7a-N与12-90％去，这取决于溶剂和温度。作出了解释。发现“烯丙基效应”（MO相互作用）可有效解释加合物的构象。

  DOI：

  10.1016/0040-4020(95)01111-0

文献信息

• Chiral N-dienyl-L-pyroglutamic esters in asymmetric hetero-Diels-Alder reactions with acylnitroso dienophiles
  作者：Jean-Bernard Behr、Albert Defoin、Joaquim Pires、Jacques Streith、Ludwig Macko、Margaretha Zehnder

  DOI：10.1016/0040-4020(95)01111-0

  日期：1996.2

  Asymmetric Diels-Alder reaction of the N-dienyl-L-pyroglutamic esters 1a-h with acyl nitroso dienophiles 4a-h gave diastereoisomeric adducts 6a-n, 7a-n with 12–90 % de, depending on solvents and temperature. An interpretation was gived. The “allylic effect” ( MO interactions) was found to be effective to account for the conformations of the adducts.

  的N二烯基- L-焦酯的不对称狄尔斯-阿尔德反应1A-H与酰基亚硝基亲二烯体4A-H ，得到非对映体加合物6A-n中，图7a-N与12-90％去，这取决于溶剂和温度。作出了解释。发现“烯丙基效应”（MO相互作用）可有效解释加合物的构象。
• Asymmetric synthesis of potent glycosidase and very potent α-mannosidase inhibitors: 4-amino-4-deoxy-l-erythrose and 4-amino-4,5-dideoxy-l-ribose
  作者：Jean-Bernard Behr、Carine Chevrier、Albert Defoin、Céline Tarnus、Jacques Streith

  DOI：10.1016/s0040-4020(02)01512-0

  日期：2003.1

  Pyrrolidine amino-sugars, cyclic iminoalditols as well as linear aminoalditols in 4-amino-L-erythrose and 4-amino-5-deoxy-L-ribose series were synthesised by asymmetric hetero-Diels-Alder reaction followed by chemical transformations. 4-Amino-4-deoxy-L-erythrose and 4-amino-4,5-dideoxy-L-ribose were potent beta-D-glucosidase, alpha-D-mannosidase, alpha- and beta-D-galactosidase inhibitors. We have shown that the ribose derivative was a very potent inhibitor of alpha-D-mannosidase. (C) 2003 Elsevier Science Ltd. All rights reserved.