methyl (E)-3-[4-[(2E,6S)-6-[tert-butyl(dimethyl)silyl]oxy-3,7-dimethylocta-2,7-dienoxy]-3-methoxyphenyl]prop-2-enoate | 220300-09-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: methyl (E)-3-[4-[(2E,6S)-6-[tert-butyl(dimethyl)silyl]oxy-3,7-dimethylocta-2,7-dienoxy]-3-methoxyphenyl]prop-2-enoate
• CAS: 220300-09-4
• 化学式: C₂₇H₄₂O₅Si
• 分子量: 474.713
• InChiKey: GQHNWQTYYCYXBD-QPNKLWIKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.95
• 重原子数：
  33
• 可旋转键数：
  14
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.52
• 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：

  methyl (E)-3-[4-[(2E,6S)-6-[tert-butyl(dimethyl)silyl]oxy-3,7-dimethylocta-2,7-dienoxy]-3-methoxyphenyl]prop-2-enoate 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 12.0h， 生成 (E)-3-{4-[(E)-(S)-6-(tert-Butyl-dimethyl-silanyloxy)-3,7-dimethyl-octa-2,7-dienyloxy]-3-methoxy-phenyl}-prop-2-en-1-ol
  参考文献：
  名称：

  Facile one-pot transformation of 2,3-epoxy alcohols into allylic alcohols: first total synthesis of (−)-4-O-(6′-hydroxy-7′(9′)-dehydro-6′,7′-dihydrogeranyl)coniferol

  摘要：

  An efficient and practical synthesis of optically active allylic alcohols from 2,3-epoxy alcohols by the in situ formation of the epoxy iodides and their subsequent reduction with phosphine hydroxyiodide has been established. Using this reaction as the key step, we synthesized (-)-4-O-(6'-hydroxy-7'(9')-dehydro-6',7'-dihydrogeranyl)coniferol. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(98)00385-1
• 作为产物：
  描述：

  3-甲氧基-4-(甲氧基甲氧基)苯甲醛 在 盐酸 、 potassium carbonate 作用下， 以 甲醇 、 丙酮 、 苯 为溶剂， 反应 10.5h， 生成 methyl (E)-3-[4-[(2E,6S)-6-[tert-butyl(dimethyl)silyl]oxy-3,7-dimethylocta-2,7-dienoxy]-3-methoxyphenyl]prop-2-enoate
  参考文献：
  名称：

  Facile one-pot transformation of 2,3-epoxy alcohols into allylic alcohols: first total synthesis of (−)-4-O-(6′-hydroxy-7′(9′)-dehydro-6′,7′-dihydrogeranyl)coniferol

  摘要：

  An efficient and practical synthesis of optically active allylic alcohols from 2,3-epoxy alcohols by the in situ formation of the epoxy iodides and their subsequent reduction with phosphine hydroxyiodide has been established. Using this reaction as the key step, we synthesized (-)-4-O-(6'-hydroxy-7'(9')-dehydro-6',7'-dihydrogeranyl)coniferol. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(98)00385-1

文献信息

• Facile one-pot transformation of 2,3-epoxy alcohols into allylic alcohols: first total synthesis of (−)-4-O-(6′-hydroxy-7′(9′)-dehydro-6′,7′-dihydrogeranyl)coniferol
  作者：Zuosheng Liu、Jiong Lan、Yulin Li

  DOI：10.1016/s0957-4166(98)00385-1

  日期：1998.11

  An efficient and practical synthesis of optically active allylic alcohols from 2,3-epoxy alcohols by the in situ formation of the epoxy iodides and their subsequent reduction with phosphine hydroxyiodide has been established. Using this reaction as the key step, we synthesized (-)-4-O-(6'-hydroxy-7'(9')-dehydro-6',7'-dihydrogeranyl)coniferol. (C) 1998 Elsevier Science Ltd. All rights reserved.