(R)-(-)-2-methyltetrahydrofuran | 63798-13-0

• 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: (R)-(-)-2-methyltetrahydrofuran
• 英文别名: 2-Methyltetrahydrofuran, (R)-；(2R)-2-methyloxolane
• CAS: 63798-13-0
• 化学式: C₅H₁₀O
• 分子量: 86.1338
• InChiKey: JWUJQDFVADABEY-RXMQYKEDSA-N

物化性质

• 沸点：
  79.9±0.0 °C(Predicted)
• 密度：
  0.863±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  6
• 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：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  (S)-四氢呋喃-2-甲酸 在 lithium aluminium tetrahydride 、 硫酸 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 23.5h， 生成 (R)-(-)-2-methyltetrahydrofuran
  参考文献：
  名称：

  α-酮酯的抗选择性催化不对称硝基羟醛反应；有趣的溶剂效应、流动反应和 API 的合成

  摘要：

  稀土金属/碱金属双金属催化剂被证明对于以反选择性方式对映选择性偶联硝基烷烃和 α-酮酯特别有效，以提供合成通用、密集功能化和光学活性的 α-硝基叔醇。手性二酰胺配体捕获两种不同的金属阳离子，通过自组装的简单混合产生具有催化能力的固相异双金属催化剂。通过在连续流动平台中成功应用于对映和非对映选择性反应，实现了固相不对称催化剂的优势。使用在结构和极性参数方面密切相关的溶剂，THF 及其甲基化同源物 2-Me-​​THF，对反应速率和立体选择性都有出乎意料的大溶剂影响。

  DOI：

  10.1021/jacs.8b08236

文献信息

• Extending the scope of enantiomer resolution by complexation gas chromatography
  作者：Volker Schurig、Waldemar Buerkle

  DOI：10.1021/ja00390a031

  日期：1982.12
• Diethoxytriphenylphosphorane: a mild, regioselective cyclodehydrating reagent for conversion of diols to cyclic ethers: stereochemistry, synthetic utility, and scope
  作者：Philip L. Robinson、Carey N. Barry、Jeffery W. Kelly、Slayton A. Evans

  DOI：10.1021/ja00304a030

  日期：1985.9
• Kotkar, Dilip; Mahajan, Satish W.; Mandal, Arun K., Journal of the Chemical Society. Perkin transactions I, 1988, p. 1749 - 1752
  作者：Kotkar, Dilip、Mahajan, Satish W.、Mandal, Arun K.、Ghosh, Pushpito K.

  DOI：——

  日期：——
• Asymmetric Hydrogenation of Olefins with Aprotic Oxygen Functionalities Catalyzed by BINAP-Ru(II) Complexes
  作者：Tetsuo Ohta、Tsutomu Miyake、Nobuo Seido、Hidenori Kumobayashi、Hidemasa Takaya

  DOI：10.1021/jo00107a014

  日期：1995.1

  Cyclic alpha,beta-unsaturated ketones, alkylidene lactones, and alkenyl ethers have been hydrogenated in high enantiomeric excesses by use of BINAP-Ru(II) complexes (BINAP = 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl) as catalysts. 2-Alkylidenecyclopentanones were hydrogenated in the presence of [RuCl(BINAP)(benzene)]Cl, Ru2Cl4(BINAP)2(NEt(3)), or Ru(OCO CH3 )(2)(BINAP) in up to 98% ee, while in the case of 2-benzylidene- and 2-(3-phenylpropylidene)cyclopentanones, enantiomeric excesses of the hydrogenation were below 50% under the same conditions. The sense of asymmetric induction as well as the enantioselectivity (95% ee) obtained in the hydrogenation of (E)-2-propylidene-gamma-butyrolactone were the same as those of the (Z)-isomer. Lactones, 2- and 4-alkylidene-gamma-butyrolactones, were converted to the corresponding saturated gamma-butyrolactones in 95% ee. Hydrogenation of diketene with the catalytic system derived from RuCl[(S)-BINAP](benzene)}Cl and triethylamine or complex Ru2Cl4[(S)-BINAP](2)(NEt(3)) established a new synthetic route to (R)-4-methyl-2-oxetanone, a promising monomer of biodegradable polymers, in up to 97% selectivity and 92% ee. Alkenyl ethers, 2-methylenetetrahydrofuran, and 2-methyl-3,4-dihydrofuran have also been hydrogenated to give 2-methyltetrahydrofuran in 91 and 87% ee, respectively.
• Regioselective cyclodehydration of chiral diols with diethoxytriphenylphosphorane, triphenylphosphine-tetrachloromethane-potassium carbonate, and triphenylphosphine-diethyl azodicarboxylate reagents. A comparative study
  作者：Philip L. Robinson、Carey N. Barry、S. Woody Bass、Susan E. Jarvis、Slayton A. Evans

  DOI：10.1021/jo00174a059

  日期：1983.12