5-methylfuryloctylcarbinol | 99423-18-4

• 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: 5-methylfuryloctylcarbinol
• 英文别名: Octyl-(5-methyl-2-furyl)-carbinol；1-(5-methyl-furan-2-yl)-nonan-1-ol；1-(5-Methylfuran-2-yl)nonan-1-ol
• CAS: 99423-18-4
• 化学式: C₁₄H₂₄O₂
• 分子量: 224.343
• InChiKey: WAQWUYSPKGHSQL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  16
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  33.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-methylfuryloctylcarbinol 在 二甲基硫 、 双氧水 、 对甲苯磺酸 作用下， 以 乙二醇二甲醚 、 乙醚 、 水 为溶剂， 反应 20.0h， 生成 6-hydroxy-6-methyl-2-octylpyran-3-one
  参考文献：
  名称：

  New procedures for the enantioselective oxidation of sulfides under stoichiometric and catalytic conditions

  摘要：

  Acid-catalyzed oxidation of 2-furylcarbinols with hydrogen peroxide affords alternatively 2-(1-hydroperoxyalkyl)furans 2 or 6-hydroperoxy-2H-pyran-3(6H)-ones 3. Compounds of the type 2 and 3 have been used Lis oxygen donors in efficient stoichiometric or catalytic procedures for the asymmetric sulfoxidation of prochiral sulfides in the presence of Ti(O-i-Pr)(4)/L-DET or Ti(O-i-Pr)(4)/(R)-BINOL/H2O systems. Positive non linear effects, (+)-NLE, were observed in the enantioselective oxidation of methyl p-tolyl sulfide, promoted by enantiomierically enriched Ti(IV)/BINOL/H2O complexes. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00326-9
• 作为产物：
  描述：

  5-甲基呋喃醛 、 正辛基镁溴盐 生成 5-methylfuryloctylcarbinol
  参考文献：
  名称：

  New procedures for the enantioselective oxidation of sulfides under stoichiometric and catalytic conditions

  摘要：

  Acid-catalyzed oxidation of 2-furylcarbinols with hydrogen peroxide affords alternatively 2-(1-hydroperoxyalkyl)furans 2 or 6-hydroperoxy-2H-pyran-3(6H)-ones 3. Compounds of the type 2 and 3 have been used Lis oxygen donors in efficient stoichiometric or catalytic procedures for the asymmetric sulfoxidation of prochiral sulfides in the presence of Ti(O-i-Pr)(4)/L-DET or Ti(O-i-Pr)(4)/(R)-BINOL/H2O systems. Positive non linear effects, (+)-NLE, were observed in the enantioselective oxidation of methyl p-tolyl sulfide, promoted by enantiomierically enriched Ti(IV)/BINOL/H2O complexes. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00326-9

文献信息

• Acid-catalyzed oxidation of furan derivatives by t-butyl hydroperoxide
  作者：Roberto Antonioletti、Luca Arista、Francesco Bonadies、Ludovica Locati、Arrigo Scettri

  DOI：10.1016/s0040-4039(00)61606-4

  日期：1993.10

  The unusual reactivity of t-butyl hydroperoxide under acid-catalysis allows the easy conversion of furan derivatives into 3(6H)-pyranones.

  叔丁基过氧化氢在酸催化下的异常反应性使得呋喃衍生物易于转化为3（6H）-吡喃酮。
• Khlebova, G. N.; Denisov, V. R.; Shevchenko, Z. A., Journal of Organic Chemistry USSR (English Translation), 1985, vol. 21, # 5, p. 906 - 909
  作者：Khlebova, G. N.、Denisov, V. R.、Shevchenko, Z. A.、Favorskaya, I. A.

  DOI：——

  日期：——
• A convenient approach to renewable hydroperoxides
  作者：Antonio Massa、Laura Palombi、Arrigo Scettri

  DOI：10.1016/s0040-4039(01)00794-8

  日期：2001.7

  2-(1-Hydroperoxyalkyl)-furans and 6-hydroperoxy-2H-pyran-3(6H)-ones are alternatively accessible by acid-catalyzed oxidation of 2-furyl alcohols with hydrogen peroxide under appropriate conditions. Representative compounds of both classes of hydroperoxides have been used, as easily renewable oxygen donors, in asymmetric sulfoxidation reactions. (C) 2001 Published by Elsevier Science Ltd.
• XLEBOVA, G. N.;DENISOV, V. R.;SHEVCHENKO, Z. A.;FAVORSKAYA, I. A., ZH. ORGAN. XIMII, 1985, 21, N 5, 998-1001
  作者：XLEBOVA, G. N.、DENISOV, V. R.、SHEVCHENKO, Z. A.、FAVORSKAYA, I. A.

  DOI：——

  日期：——
• New procedures for the enantioselective oxidation of sulfides under stoichiometric and catalytic conditions
  作者：Antonio Massa、Francesca R Siniscalchi、Valeria Bugatti、Alessandra Lattanzi、Arrigo Scettri

  DOI：10.1016/s0957-4166(02)00326-9

  日期：2002.7

  Acid-catalyzed oxidation of 2-furylcarbinols with hydrogen peroxide affords alternatively 2-(1-hydroperoxyalkyl)furans 2 or 6-hydroperoxy-2H-pyran-3(6H)-ones 3. Compounds of the type 2 and 3 have been used Lis oxygen donors in efficient stoichiometric or catalytic procedures for the asymmetric sulfoxidation of prochiral sulfides in the presence of Ti(O-i-Pr)(4)/L-DET or Ti(O-i-Pr)(4)/(R)-BINOL/H2O systems. Positive non linear effects, (+)-NLE, were observed in the enantioselective oxidation of methyl p-tolyl sulfide, promoted by enantiomierically enriched Ti(IV)/BINOL/H2O complexes. (C) 2002 Elsevier Science Ltd. All rights reserved.