8-hydroxy-6-methyl-5(E)-octen-2-one ethylene acetal | 110589-84-9

• 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: 8-hydroxy-6-methyl-5(E)-octen-2-one ethylene acetal
• 英文别名: (E)-3-methyl-6-(2-methyl-1,3-dioxolan-2-yl)hex-3-en-1-ol
• CAS: 110589-84-9
• 化学式: C₁₁H₂₀O₃
• 分子量: 200.278
• InChiKey: BRZHODCXGUDPKS-ONNFQVAWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.86
• 重原子数：
  14.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  38.69
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  8-hydroxy-6-methyl-5(E)-octen-2-one ethylene acetal 在 盐酸 、 sodium tetrahydroborate 、 四(三苯基膦)钯 、 magnesium 、 溶剂黄146 、 sodium iodide 、 zinc(II) chloride 作用下， 以 四氢呋喃 、 吡啶 、 甲醇 、 水 、 丙酮 为溶剂， 反应 62.0h， 生成 (+)-cis-12-<2-(hydroxymethyl)-3,3-dimethylcyclopropyl>-6,10-dimethyl-5(E),9(E)-dodecadien-2-one
  参考文献：
  名称：

  Synthesis of macrocyclic terpenoid hydrocarbons by intramolecular carbonyl coupling: bicyclogermacrene, lepidozene, and casbene

  摘要：

  DOI：

  10.1021/jo00231a012
• 作为产物：
  描述：

  8-(isopropoxydimethylsilyl)-6-methyl-5(E)-octen-2-one ethylene acetal 在 双氧水 、 sodium carbonate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 1.0h， 以74%的产率得到8-hydroxy-6-methyl-5(E)-octen-2-one ethylene acetal
  参考文献：
  名称：

  Synthesis of macrocyclic terpenoid hydrocarbons by intramolecular carbonyl coupling: bicyclogermacrene, lepidozene, and casbene

  摘要：

  DOI：

  10.1021/jo00231a012

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.
• MCMURRY, JOHN E.;BOSCH, GREGORY K., J. ORG. CHEM., 52,(1987) N 22, 4885-4893
  作者：MCMURRY, JOHN E.、BOSCH, GREGORY K.

  DOI：——

  日期：——