trans-2-Methyl-3-hydroxy-tetrahydrofuran | 114580-34-6

• 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: trans-2-Methyl-3-hydroxy-tetrahydrofuran
• 英文别名: (2R,3S)-2-methyloxolan-3-ol
• CAS: 114580-34-6
• 化学式: C₅H₁₀O₂
• 分子量: 102.133
• InChiKey: ZFVWBUVYNPLIIS-UHNVWZDZSA-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：

  trans-2-Methyl-3-hydroxy-tetrahydrofuran 生成 (2R,3R)-cis-2-methyltetrahydrofuran-3-thiol acetate
  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：

  (2R,3S)-trans-2-methyl-3-(p-nitrobenzoyloxy)tetrahydrofuran 在 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 5.0h， 以90%的产率得到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

文献信息

• Hydroboration. 83. Asymmetric hydroboration of representative cis disubstituted and heterocyclic olefins with dicaranylboranes of high enantiomeric purity
  作者：Herbert C. Brown、J. V. N. Vara Prasad、Marek Zaidlewicz

  DOI：10.1021/jo00248a004

  日期：1988.6
• Stereocontrolled Formation of Functionalized erythro-1,2-Diols via Hydroboration of 2-Alkyl-4,5-dihydrofurans
  作者：Roger Amouroux、Abdelmalik Slassi、Christine Saluzzo

  DOI：10.3987/com-93-6428

  日期：——

  trans-2-Alkyl-3-hydroxytetrahydrofurans, prepared by the stereospecific hydroboration / oxidation reaction of 2-alkyl-4,5-dihydrofurans, were regioselectively cleaved with (CH3)3SiCl / NaI to afford 1-iodo-erythro-3,4-diols in CH3CN or the corresponding acetonide derivatives in CH3COCH3.
• 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：——
• BROWN, H. C.;VARA, PRASAD, J. V. N.;ZEE, SHENG-HSU, J. ORG. CHEM., 1985, 50, N 10, 1582-1589
  作者：BROWN, H. C.、VARA, PRASAD, J. V. N.、ZEE, SHENG-HSU

  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.