2-methyl-2-phenyltetrahydrofuran-6-ol | 133549-38-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: 2-methyl-2-phenyltetrahydrofuran-6-ol
• 英文别名: 6-methyl-6-phenyloxan-2-ol
• CAS: 133549-38-9
• 化学式: C₁₂H₁₆O₂
• 分子量: 192.258
• InChiKey: XQFGSUDKUPGOGN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.42
• 重原子数：
  14.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  29.46
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  2-methyl-2-phenyltetrahydrofuran-6-ol 在 jones reagent 作用下， 生成 6-methyl-6-phenyltetrahydropyran-2-one
  参考文献：
  名称：

  Direct synthesis of δ-lactones from 2-(3-lithiopropyl)-1,3-dioxolane and carbonyl compounds

  摘要：

  DOI：

  10.1016/s0040-4039(00)97466-5
• 作为产物：
  描述：

  5-[1,3]dioxolan-2-yl-2-phenyl-pentan-2-ol 在 盐酸 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 2-methyl-2-phenyltetrahydrofuran-6-ol
  参考文献：
  名称：

  Direct synthesis of δ-lactones from 2-(3-lithiopropyl)-1,3-dioxolane and carbonyl compounds

  摘要：

  DOI：

  10.1016/s0040-4039(00)97466-5

文献信息

• Masked lithium bishomoenolates: useful intermediates in organic synthesis
  作者：Diego J. Ramon、Miguel Yus

  DOI：10.1021/jo00012a012

  日期：1991.6

  The lithiation of the chloro ketals 9 with lithium naphthalenide at -78-degrees-C led to the corresponding masked lithium bishomoenolates 4, which are stable species under these conditions and react with different electrophilic reagents (H2O, D2O, i-PrCHO, PhCHO, MeCOEt, (activated CH2)4CO, (activated CH2)5CO, (activated CH2)7CO, PhCOMe, c-C3H5COPh, PhCN, HCONMe2, PrCO activated N(CH2)4, PhCO activated N(CH2)4, PhCOCl, EtOCOCl, PhCHNPh, and (PhCH2S)2) to give, after hydrolysis with water, the corresponding bifunctionalized compounds 10a-22a, 10b-22b, and 10c-15c. When alkyl halides were used as electrophiles the reaction failed. In the presence of a catalytic amount of the complex CuBr.Me2S, the same reaction with alpha,beta-unsaturated ketones (methyl vinyl ketone or 2-cyclohexanone) yielded the expected products of a 1,4-addition 25a-c and 26b. The deprotection of the masked carbonyl group was easily done by treatment with 2 N hydrochloric acid in THF, so as examples, compounds 27a-29a, 30b, 31b, 32c, and 33c were isolated. The transformation of hemiacetals of the type 27a into substituted tetrahydropyrans was carried out by means of compounds of the type R3SiNu (Nu = H, allyl, CN) in the presence of BF3, so products 34a-41a, 42b, and 43b were prepared. Finally, the in situ oxidation of the deprotected products of the type 27a-arising from the reaction of bishomoenolate 4a with carbonyl compounds-with Jones reagent (for ketones derivatives) or PCC (for aldehydes derivatives) led to the corresponding delta-lactones 44-57.
• Direct synthesis of δ-lactones from 2-(3-lithiopropyl)-1,3-dioxolane and carbonyl compounds
  作者：Diego J. Ramón、Miguel Yus

  DOI：10.1016/s0040-4039(00)97466-5

  日期：——