2-(4-methoxybenzyloxy)pent-4-enoic acid (S,Z)-4-(tert-butyldiphenylsilanyloxy)-1-isopropylbut-2-enyl ester | 1029539-82-9

• 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: 2-(4-methoxybenzyloxy)pent-4-enoic acid (S,Z)-4-(tert-butyldiphenylsilanyloxy)-1-isopropylbut-2-enyl ester
• 英文别名: [(Z,3S)-6-[tert-butyl(diphenyl)silyl]oxy-2-methylhex-4-en-3-yl] 2-[(4-methoxyphenyl)methoxy]pent-4-enoate
• CAS: 1029539-82-9
• 化学式: C₃₆H₄₆O₅Si
• 分子量: 586.844
• InChiKey: JGHXAOBZYZTAKA-LNRGWTQNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.86
• 重原子数：
  42
• 可旋转键数：
  17
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  三甲基氯硅烷 、 2-(4-methoxybenzyloxy)pent-4-enoic acid (S,Z)-4-(tert-butyldiphenylsilanyloxy)-1-isopropylbut-2-enyl ester 在 正丁基锂 、 六甲基二硅氮烷 作用下， 以 正己烷 、 甲苯 为溶剂， 反应 0.75h， 生成
  参考文献：
  名称：

  Directed Diastereoselectivity in the Asymmetric Claisen/Metathesis Reaction Sequence

  摘要：

  The Claisen/metathesis sequence is a versatile synthetic tool for the synthesis of quaternary hydroxy and amino acid carbocycles. By correctly choosing both the configuration of the allylic alcohol and the double bond geometry, specific access to any one of four possible stereoisomers is possible in good yield and excellent diastereoselectivity. The enantiomerically pure allylic alcohols are easily obtained by addition of terminal alkynes to aldehydes. Controlled reduction of the triple bond then gives the desired double bond geometry.

  DOI：

  10.1021/jo800496h
• 作为产物：
  描述：

  (S,Z)-6-((tert-butyldiphenylsilyl)oxy)-2-methylhex-4-en-3-ol 、 2-(4-methoxybenzyloxy)pent-4-enoic acid 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 以95%的产率得到2-(4-methoxybenzyloxy)pent-4-enoic acid (S,Z)-4-(tert-butyldiphenylsilanyloxy)-1-isopropylbut-2-enyl ester
  参考文献：
  名称：

  Directed Diastereoselectivity in the Asymmetric Claisen/Metathesis Reaction Sequence

  摘要：

  The Claisen/metathesis sequence is a versatile synthetic tool for the synthesis of quaternary hydroxy and amino acid carbocycles. By correctly choosing both the configuration of the allylic alcohol and the double bond geometry, specific access to any one of four possible stereoisomers is possible in good yield and excellent diastereoselectivity. The enantiomerically pure allylic alcohols are easily obtained by addition of terminal alkynes to aldehydes. Controlled reduction of the triple bond then gives the desired double bond geometry.

  DOI：

  10.1021/jo800496h

文献信息

• Directed Diastereoselectivity in the Asymmetric Claisen/Metathesis Reaction Sequence
  作者：Nicolas P. Probst、Arnaud Haudrechy、Karen Plé

  DOI：10.1021/jo800496h

  日期：2008.6.1

  The Claisen/metathesis sequence is a versatile synthetic tool for the synthesis of quaternary hydroxy and amino acid carbocycles. By correctly choosing both the configuration of the allylic alcohol and the double bond geometry, specific access to any one of four possible stereoisomers is possible in good yield and excellent diastereoselectivity. The enantiomerically pure allylic alcohols are easily obtained by addition of terminal alkynes to aldehydes. Controlled reduction of the triple bond then gives the desired double bond geometry.