(2R,3R)-cis-2-methyl-3-hydroxytetrahydrofuran | 20086-87-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四氢呋喃
• 英文名称: (2R,3R)-cis-2-methyl-3-hydroxytetrahydrofuran
• 英文别名: (2SR,3SR)-cis-2-Methyltetrahydrofuran-3-ol；cis-2-Methyl-3-hydroxytetrahydrofuran；(2R,3R)-2-methyloxolan-3-ol
• CAS: 20086-87-7；20086-88-8；29848-44-0；50403-32-2；50403-34-4；114580-34-6；114611-74-4
• 化学式: C₅H₁₀O₂
• 分子量: 102.133
• InChiKey: ZFVWBUVYNPLIIS-RFZPGFLSSA-N

物化性质

• 沸点：
  182.6±8.0 °C(Predicted)
• 密度：
  1.055±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  7
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2R,3R)-cis-2-methyl-3-hydroxytetrahydrofuran 在 偶氮二甲酸二异丙酯 、 三苯基膦 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 5.0h， 生成 trans-2-Methyl-3-hydroxy-tetrahydrofuran
  参考文献：
  名称：

  Enantioselective Syntheses and Sensory Properties of 2-Methyl-tetrahydrofuran-3-thiol Acetates

  摘要：

  The enantioselective synthesis of four stereoisomers of 2-methyl-tetrahydrofuran-3-thiol acetate was achieved. The two enantiomers of the important intermediate cis-2-methyl-3-hydroxy-tetrahydrofuran were obtained by Sharpless asymmetric dihydroxylation (AD), whereas the two enantiomers of trans-2-methyl-3-hydroxy-tetrahydrofuran were derived from the corresponding optically active cis-isomers by Mitsunobu reaction. Each stereoisomer of 2-methyl-3-hydroxy-tetrahydrofuran went through mesylation and nucleophilic substitution to afford the corresponding product with specific configuration. (2R,3S)- and (2R,3R)-2-methyl-tetrahydrofuran-3-thiol acetate were obtained in 80% ee, whereas the (2S,3R)- and (2S,3S)-isomers were in 62% ee. The odor properties of the synthesized four stereoisomers were evaluated by gas chromatography-olfactometry (GC-O), which revealed perceptible differences among stereoisomers both in odor features and in intensities.

  DOI：

  10.1021/jf503866x
• 作为产物：
  描述：

  2-((2R,3S)-3-methyloxiran-2-yl)ethanol 在 间苯二甲酸 、 三正丁基甲氧基锡 作用下， 生成 (2R,3R)-cis-2-methyl-3-hydroxytetrahydrofuran 、 (S)-(R)-1-Oxetan-2-yl-ethanol
  参考文献：
  名称：

  环氧乙烷-乙醇的间位交换产物是环氧烷烃。奥西兰的配置影响

  摘要：

  环氧乙烷-乙醇通过烷氧基锡化合物转位成环氧乙烷-2-甲醇和/或环氧乙烷-3-醇（四氢呋喃-3-醇）取决于环氧乙烷的构型。顺式构型更适合于形成最小的环。立体位阻不足以解释结果。

  DOI：

  10.1016/s0040-4039(00)77404-1

文献信息

• Cyclic sulfolanes as novel and high-affinity P2 ligands for HIV-1 protease inhibitors
  作者：Arun K. Ghosh、Wayne J. Thompson、Hee Yoon Lee、Sean P. McKee、Peter M. Munson、Tien T. Duong、Paul L. Darke、Joan A. Zugay、Emilio A. Emini

  DOI：10.1021/jm00059a019

  日期：1993.4
• BATS, J. -P.;MOULINES, J.;PICARD, P.;LECLERCQ, D., TETRAHEDRON, 1982, 38, N 14, 2139-2146
  作者：BATS, J. -P.、MOULINES, J.、PICARD, P.、LECLERCQ, D.

  DOI：——

  日期：——
• Enantioselective Syntheses and Sensory Properties of 2-Methyl-tetrahydrofuran-3-thiol Acetates
  作者：Yifeng Dai、Junqiang Shao、Shaoxiang Yang、Baoguo Sun、Yongguo Liu、Ting Ning、Hongyu Tian

  DOI：10.1021/jf503866x

  日期：2015.1.21

  The enantioselective synthesis of four stereoisomers of 2-methyl-tetrahydrofuran-3-thiol acetate was achieved. The two enantiomers of the important intermediate cis-2-methyl-3-hydroxy-tetrahydrofuran were obtained by Sharpless asymmetric dihydroxylation (AD), whereas the two enantiomers of trans-2-methyl-3-hydroxy-tetrahydrofuran were derived from the corresponding optically active cis-isomers by Mitsunobu reaction. Each stereoisomer of 2-methyl-3-hydroxy-tetrahydrofuran went through mesylation and nucleophilic substitution to afford the corresponding product with specific configuration. (2R,3S)- and (2R,3R)-2-methyl-tetrahydrofuran-3-thiol acetate were obtained in 80% ee, whereas the (2S,3R)- and (2S,3S)-isomers were in 62% ee. The odor properties of the synthesized four stereoisomers were evaluated by gas chromatography-olfactometry (GC-O), which revealed perceptible differences among stereoisomers both in odor features and in intensities.
• Transposition des oxirannes-ethanols par l'intermediaire d'alcoxyetains. Influence de la configuration de l'oxiranne
  作者：J.-P Bats、J Moulines、P Picard、D Leclercq

  DOI：10.1016/s0040-4039(00)77404-1

  日期：1980.1

  The transposition of oxirane-ethanols, through alkoxytin compounds, into oxetane-2-methanols and/or oxolan-3-ols (tetrahydrofuran-3-ols) is dependent upon the oxirane configuration. Cis configuration is more suitable for the formation of the smallest ring. Steric hindrance is not sufficient enough to explain the results.

  环氧乙烷-乙醇通过烷氧基锡化合物转位成环氧乙烷-2-甲醇和/或环氧乙烷-3-醇（四氢呋喃-3-醇）取决于环氧乙烷的构型。顺式构型更适合于形成最小的环。立体位阻不足以解释结果。