(2E,4S)-4-<(benzyl)oxy>-2-penten-1-yl p-toluenesulfonate | 243841-19-2

• 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: (2E,4S)-4-<(benzyl)oxy>-2-penten-1-yl p-toluenesulfonate
• 英文别名: [(E,4S)-4-phenylmethoxypent-2-enyl] 4-methylbenzenesulfonate
• CAS: 243841-19-2
• 化学式: C₁₉H₂₂O₄S
• 分子量: 346.447
• InChiKey: KDVXBNFDPYFPLD-LXXRFIIISA-N

物化性质

• 沸点：
  488.2±45.0 °C(predicted)
• 密度：
  1.164±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  24
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  61
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  乙酰乙酸乙酯 、 (2E,4S)-4-<(benzyl)oxy>-2-penten-1-yl p-toluenesulfonate 在 lithium hydroxide 作用下， 生成 ethyl 2-acetyl-(4E,6S)-6-<(benzyl)oxy>-4-heptenoate
  参考文献：
  名称：

  Diastereoselective synthesis of enantiopure 5-[2-(alkoxyalkyl)-1-(hydroperoxypropyl)]-3-alkoxycarbonyl-2-alkyl furans

  摘要：

  The diastereoselective approach to enantiomerically pure furyl hydroperoxides of general type 1 has been accomplished starting from (S)-(-)-ethyl lactate. In the first part of the synthesis the alkylating reagents 7a,b were efficiently produced to be used in the second part for a 4-step known methodology to obtain furyl hydroperoxides. The most relevant transformation of the synthesis is the first reported diastereoselective iodoenoletherification of 2-acetyl-4-heptenoate esters 8a,b possessing a phi-chiral center. Furthermore, the final radical oxidation performed on (E)-5-alkylidene-4,5-dihydrofurans 11a,b led to formation of hydroperoxides (S,S)-12a,b in a diastereocontrolled manner due to 1,2-asymmetric induction. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00187-1
• 作为产物：
  描述：

  (2E,4S)-4-<(benzyl)oxy>-2-pentenol 、 对甲苯磺酰氯 在 氢氧化钾 、 四丁基硫酸氢铵 作用下， 以 苯 为溶剂， 以95%的产率得到(2E,4S)-4-<(benzyl)oxy>-2-penten-1-yl p-toluenesulfonate
  参考文献：
  名称：

  Diastereoselective synthesis of enantiopure 5-[2-(alkoxyalkyl)-1-(hydroperoxypropyl)]-3-alkoxycarbonyl-2-alkyl furans

  摘要：

  The diastereoselective approach to enantiomerically pure furyl hydroperoxides of general type 1 has been accomplished starting from (S)-(-)-ethyl lactate. In the first part of the synthesis the alkylating reagents 7a,b were efficiently produced to be used in the second part for a 4-step known methodology to obtain furyl hydroperoxides. The most relevant transformation of the synthesis is the first reported diastereoselective iodoenoletherification of 2-acetyl-4-heptenoate esters 8a,b possessing a phi-chiral center. Furthermore, the final radical oxidation performed on (E)-5-alkylidene-4,5-dihydrofurans 11a,b led to formation of hydroperoxides (S,S)-12a,b in a diastereocontrolled manner due to 1,2-asymmetric induction. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00187-1

文献信息

• Diastereoselective synthesis of enantiopure 5-[2-(alkoxyalkyl)-1-(hydroperoxypropyl)]-3-alkoxycarbonyl-2-alkyl furans
  作者：Alessandra Lattanzi、Francesco Sagulo、Arrigo Scettri

  DOI：10.1016/s0957-4166(99)00187-1

  日期：1999.5

  The diastereoselective approach to enantiomerically pure furyl hydroperoxides of general type 1 has been accomplished starting from (S)-(-)-ethyl lactate. In the first part of the synthesis the alkylating reagents 7a,b were efficiently produced to be used in the second part for a 4-step known methodology to obtain furyl hydroperoxides. The most relevant transformation of the synthesis is the first reported diastereoselective iodoenoletherification of 2-acetyl-4-heptenoate esters 8a,b possessing a phi-chiral center. Furthermore, the final radical oxidation performed on (E)-5-alkylidene-4,5-dihydrofurans 11a,b led to formation of hydroperoxides (S,S)-12a,b in a diastereocontrolled manner due to 1,2-asymmetric induction. (C) 1999 Elsevier Science Ltd. All rights reserved.