1-cyclohexyl-3-methylenepent-4-en-1-ol

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-cyclohexyl-3-methylenepent-4-en-1-ol
• 英文别名: 1-Cyclohexyl-3-methylidenepent-4-en-1-ol
• 化学式: C₁₂H₂₀O
• 分子量: 180.29
• InChiKey: UCUGWBXNKPNURP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 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 、 1-cyclohexyl-3-methylenepent-4-en-1-ol 在 copper(l) iodide 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以76%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：

  环己烷基甲醛 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 1-cyclohexyl-3-methylenepent-4-en-1-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

• In Turn or in Reverse Palladium-Catalyzed Carbonyl Allylation and Diels-Alder Reaction by 2-Methylene-3-buten-1-ol
  作者：Yoshiro Masuyama、Manabu Fuse、Yasuhiko Kurusu

  DOI：10.1246/cl.1993.1199

  日期：1993.7

  Using PdCl2(PhCN)2-SnCl2, 2-methylene-3-buten-2-ol causes carbonyl allylation of various aldehydes to afford 1-substituted-3-methylene-4-penten-1-ols; the Diels-Alder reaction of those with dienophiles produces 1-(2-hydroxyethyl)cyclohexenes. Diels-Alder reaction of 2-methylene-3-buten-1-ol with dienophiles followed by carbonyl allylation produces structurally isomeric 1-methylene-2-(hydroxymethyl)cyclohexanes

  使用 PdCl2(PhCN)2-SnCl2，2-methylene-3-buten-2-ol 引起各种醛的羰基烯丙基化，得到 1-取代的 3-methylene-4-penten-1-ols；那些与亲二烯体的狄尔斯-阿尔德反应产生 1-(2-羟乙基) 环己烯。2-亚甲基-3-丁烯-1-醇与亲二烯体的狄尔斯-阿尔德反应，随后羰基烯丙基化产生结构异构的 1-亚甲基-2-（羟甲基）环己烷。
• Dienyl Homoallyl Alcohols via Palladium Catalyzed Ene-Type Reaction of Aldehydes with 1,3-Dienes
  作者：Masahiro Fukushima、Daiki Takushima、Masanari Kimura

  DOI：10.1021/ja1072417

  日期：2010.11.24

  The combination of Pd catalyst and Xantphos ligand in the presence of Et(3)B nicely promotes the allylation of aldehydes with conjugated dienes to provide dienyl homoallyl alcohols in excellent yields. The reaction occurs selectively at the C-C double bond bearing higher electron density.

  在 Et(3)B 存在下，Pd 催化剂和 Xantphos 配体的组合很好地促进了醛与共轭二烯的烯丙基化，以优异的产率提供二烯基高烯丙醇。该反应选择性地发生在具有较高电子密度的 CC 双键上。
• 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.