5-methylene-2,2-dimethyl-6-hepten-3-ol | 134441-01-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-methylene-2,2-dimethyl-6-hepten-3-ol
• 英文别名: 2,2-Dimethyl-5-methylidenehept-6-en-3-ol
• CAS: 134441-01-3
• 化学式: C₁₀H₁₈O
• 分子量: 154.252
• InChiKey: CBXPFSVBXLMLJS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  11
• 可旋转键数：
  4
• 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：

  碘代三甲硅烷 、 5-methylene-2,2-dimethyl-6-hepten-3-ol 在 copper(l) iodide 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以80%的产率得到
  参考文献：
  名称：

  1,4-Hydroiodination of Dienyl Alcohols with TMSI To Form Homoallylic Alcohols Containing a Multisubstituted Z-Alkene and Application to Prins Cyclization

  摘要：

  A regioselective 1,4-hydroiodination of dienyl alcohols has been developed using trimethylsilyl iodide as Lewis acid and iodide source. A range of homoallylic alcohols containing a multisubstituted Z-alkene was synthesized with good to excellent configurational control. The approach was applied in sequential hydroiodination/Prins cyclization to afford multisubstituted tetrahydropyrans diastereoselectively.

  DOI：

  10.1021/acs.orglett.5b00485
• 作为产物：
  描述：

  特戊醛 在 tin 、 氢溴酸 、 甲基氯化镁 作用下， 以 四氢呋喃 、 乙醚 、 水 为溶剂， 反应 6.41h， 生成 5-methylene-2,2-dimethyl-6-hepten-3-ol
  参考文献：
  名称：

  1,4-Hydroiodination of Dienyl Alcohols with TMSI To Form Homoallylic Alcohols Containing a Multisubstituted Z-Alkene and Application to Prins Cyclization

  摘要：

  A regioselective 1,4-hydroiodination of dienyl alcohols has been developed using trimethylsilyl iodide as Lewis acid and iodide source. A range of homoallylic alcohols containing a multisubstituted Z-alkene was synthesized with good to excellent configurational control. The approach was applied in sequential hydroiodination/Prins cyclization to afford multisubstituted tetrahydropyrans diastereoselectively.

  DOI：

  10.1021/acs.orglett.5b00485

文献信息

• On the direct metalation of isoprene
  作者：P.A.A. Klusener、L. Tip、L. Brandsma

  DOI：10.1016/s0040-4020(01)96114-9

  日期：1991.3

  Isoprene has been metalated in tetrahydrofuran with an excess of sterically hindered potassium dialkylamides, prepared by combining equimolar amounts of the corresponding lithium amide and potassium tert-butoxide. Subsequent reaction with oxirane, alkyl bromides, and pivaldehyde gave the expected coupling products in reasonable yields. Coupling with (CH3)2CHCH2CHO and (CH3)2CCHCHO afforded the bark

  异戊二烯已在四氢呋喃中与过量的空间受阻的二烷基酰胺化钾金属化，这是通过等摩尔量的相应的氨基化锂和叔丁醇钾的混合制备的。随后与环氧乙烷，烷基溴化物和苯乙醛的反应以合理的收率得到了预期的偶联产物。与（CH 3）2 CHCH 2 CH ＝ O和（CH 3）2 C ＝CHCH ＝O偶合，以低收率得到树皮甲虫信息素（±）-异酚和（±）-异戊二烯酚。
• 1,4-Hydroiodination of Dienyl Alcohols with TMSI To Form Homoallylic Alcohols Containing a Multisubstituted <i>Z</i>-Alkene and Application to Prins Cyclization
  作者：Yongjin Xu、Zhiping Yin、Xinglong Lin、Zubao Gan、Yanyang He、Lu Gao、Zhenlei Song

  DOI：10.1021/acs.orglett.5b00485

  日期：2015.4.17

  A regioselective 1,4-hydroiodination of dienyl alcohols has been developed using trimethylsilyl iodide as Lewis acid and iodide source. A range of homoallylic alcohols containing a multisubstituted Z-alkene was synthesized with good to excellent configurational control. The approach was applied in sequential hydroiodination/Prins cyclization to afford multisubstituted tetrahydropyrans diastereoselectively.