(E)-3,7-dimethyl-3,7-octadien-1-ol | 19788-92-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (E)-3,7-dimethyl-3,7-octadien-1-ol
• 英文别名: trans-3.7-Dimethyl-octadien-(3.7)-ol-(1)；(E)-3,7-dimethyl-octa-3,7-dien-1-ol；3,7-dimethyl-octa-3,7-dien-1-ol；(3E)-3,7-dimethylocta-3,7-dien-1-ol
• CAS: 19788-92-2
• 化学式: C₁₀H₁₈O
• 分子量: 154.252
• InChiKey: FIXKTWNYKKKKSC-UXBLZVDNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  11
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (E)-3,7-dimethyl-3,7-octadien-1-ol 以 吡啶 为溶剂， 生成 (E)-12-benzyloxy-2,6-dimethyl-dodeca-1,5-dien-9-yne
  参考文献：
  名称：

  Nonenzymic, biogenetic-like cyclization of a tetraenic acetal to produce the D-homosteroid nucleus

  摘要：

  DOI：

  10.1021/ja00819a041
• 作为产物：
  描述：

  (+-)-Methyl-cyclopropyl-<1-ethoxy-carbonyl-3-methyl-buten-(3)-yl>-keton 在 barium dihydroxide 、 lithium aluminium tetrahydride 作用下， 以 乙醚 、 水 为溶剂， 反应 8.0h， 生成 (E)-3,7-dimethyl-3,7-octadien-1-ol
  参考文献：
  名称：

  A highly stereoselective synthesis of trans-trisubstituted olefinic bonds

  摘要：

  DOI：

  10.1021/ja01013a027

文献信息

• Chemistry of dioxenium cations. Synthetic and mechanistic studies on the stereocontrolled formation of tetrahydropyrans from homoallylic alcohols and ortho esters
  作者：Francoise Perron-Sierra、Michele A. Promo、Van A. Martin、Kim F. Albizati

  DOI：10.1021/jo00021a043

  日期：1991.10

  Despite their long history, dioxenium cations are underutilized reactive synthetic intermediates. It was found that ortho esters and homoallylic alcohols in the presence of Lewis acids provide 4-heterosubstituted pyranosides in a stereoselective manner. The mechanistic course of events was supported by control experiments and synthesis of a putative mixed ortho ester intermediate which exhibited identical reactivity. A transition state for termination of the dioxenium cation-olefin cyclization is proposed, involving intramolecular delivery of chloride by a coordinated tin species. Structure-reactivity relationships indicate that a cation-stabilizing substituent (alkyl or alkoxy) at the internal position of the olefin is required for cyclization. A variety of 3-alkyl-substituted homoallylic alcohols cyclize cleanly to substituted 2-alkoxytetrahydropyrans in good yield. beta-silyloxy silyl enol ethers were found to smoothly provide 4-oxotetrahydropyranosides when subjected to the same reaction conditions. For these substrates, the course of the cyclization proceeds in a different manner involving a rapid intermolecular Mukaiyama aldol condensation followed by transacetalization.
• US3996303A
  申请人：——

  公开号：US3996303A

  公开（公告）日：1976-12-07
• A highly stereoselective synthesis of trans-trisubstituted olefinic bonds
  作者：Stephen F. Brady、Marcia A. Ilton、William S. Johnson

  DOI：10.1021/ja01013a027

  日期：1968.5
• Nonenzymic, biogenetic-like cyclization of a tetraenic acetal to produce the D-homosteroid nucleus
  作者：William S. Johnson、Koenraad Wiedhaup、Stephen F. Brady、Gary L. Olson

  DOI：10.1021/ja00819a041

  日期：1974.6