cis-5-methyl-5-(4-methyl-3-pentenyl)tetrahydro-2-furanol

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧唑烯
• 英文名称: cis-5-methyl-5-(4-methyl-3-pentenyl)tetrahydro-2-furanol
• 英文别名: (2R,5R)-5-methyl-5-(4-methylpent-3-enyl)oxolan-2-ol
• 化学式: C₁₁H₂₀O₂
• 分子量: 184.279
• InChiKey: XMUFJLLRDCVSDT-GHMZBOCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  芳樟醇 、 一氧化碳 在 methoxy(cyclooctadiene)rhodium(I) dimer 、 trisodium tris(3-sulfophenyl)phosphine 、 氢气 、 十六烷基三甲基氯化铵 作用下， 以 水 、 甲苯 为溶剂， 80.0 ℃ 、6.08 MPa 条件下， 反应 2.0h， 以98%的产率得到
  参考文献：
  名称：

  由可再生资源合成香料化合物：无环萜烯的水性双相加氢甲酰化

  摘要：

  铑催化的无环萜烯化合物的羰基化反应，即β-香茅烯，芳樟醇和橙花醇在水/甲苯双相系统中进行。阳离子表面活性剂十六烷基三甲基氯化铵的加入显着提高了反应速率，表面活性剂的作用取决于底物。使用水溶性膦配体将铑催化剂固定在水中（一种对环境有益的溶剂）中，而将非极性产物收集在有机相中。通过关闭磁力搅拌器并将混合物冷却至室温，很容易实现完全的相分离。芳樟醇和橙花醇提供了出色的立体选择性的环状半缩醛，而β-香茅烯的加氢甲酰化反应生成了两种异构的醛，其线性与支链产物的比率约为85/15。

  DOI：

  10.1039/c4cy01020e

文献信息

• Synthesis of fragrance compounds from acyclic monoterpenes: Rhodium catalyzed hydroformylation and tandem hydroformylation/acetalization of linalool and β-citronellene
  作者：Camila G. Vieira、Eduardo N. dos Santos、Elena V. Gusevskaya

  DOI：10.1016/j.apcata.2013.06.037

  日期：2013.9

  Rhodium-catalyzed hydroformylation of acyclic monoterpenic compounds, i.e., linalool and beta-citronellene, was studied in toluene and ethanol solutions in the presence of PPh3 or P(O-o-(BuPh)-Bu-t)(3) ligands. Although both substrates have a monosubstituted terminal double bond, they show different behavior under the hydroformylation conditions. In toluene, linalool gave almost quantitatively a cyclic hemiacetal: whereas the hydroformylation of beta-citronellene resulted in two isomeric aldehydes also in a nearly quantitative combined yield. The reactions occurred approximately two times faster in ethanol than in toluene giving the corresponding acetals even in the absence of additional acid co-catalysts. In the absence of phosphorous ligands, linalool (differently from beta-citronellene) was very resistant to hydroformylation probably due to the binding with rhodium through both the double bond and the hydroxyl group to form stable chelates. The P(O-o-(BuPh)-Bu-t)(3) ligand exerted a remarkable effect on the reactivity of both substrates accelerating the reactions by 5-20 times as compared to the system with PPh3. Several fragrance compounds were obtained in high yields through a simple one-pot procedure starting from the substrates easily available from natural bio-renewable resources. (C) 2013 Elsevier B.V. All rights reserved.
• Synthesis of fragrance compounds from renewable resources: the aqueous biphasic hydroformylation of acyclic terpenes
  作者：Camila G. Vieira、Marina C. de Freitas、Kelley C. B. de Oliveira、Amanda de Camargo Faria、Eduardo N. dos Santos、Elena V. Gusevskaya

  DOI：10.1039/c4cy01020e

  日期：——

  increased the reaction rates, with the surfactant effect being substrate dependent. A water-soluble phosphine ligand was used to immobilize the rhodium catalyst in water, an environmentally benign solvent, whereas non-polar products were collected in the organic phase. A complete phase separation was easily achieved by switching the magnetic stirrer off and cooling the mixture to room temperature. Linalool

  铑催化的无环萜烯化合物的羰基化反应，即β-香茅烯，芳樟醇和橙花醇在水/甲苯双相系统中进行。阳离子表面活性剂十六烷基三甲基氯化铵的加入显着提高了反应速率，表面活性剂的作用取决于底物。使用水溶性膦配体将铑催化剂固定在水中（一种对环境有益的溶剂）中，而将非极性产物收集在有机相中。通过关闭磁力搅拌器并将混合物冷却至室温，很容易实现完全的相分离。芳樟醇和橙花醇提供了出色的立体选择性的环状半缩醛，而β-香茅烯的加氢甲酰化反应生成了两种异构的醛，其线性与支链产物的比率约为85/15。