(+)-(2R,3S)-3-methoxy-2-butanol | 336620-64-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (+)-(2R,3S)-3-methoxy-2-butanol
• 英文别名: (2R,3S)-3-methoxybutan-2-ol
• CAS: 336620-64-5
• 化学式: C₅H₁₂O₂
• 分子量: 104.149
• InChiKey: HJHFJCUIVDTESF-UHNVWZDZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  7
• 可旋转键数：
  2
• 环数：
  0.0
• 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,3S)-3-methoxy-2-butanol 在 sodium 作用下， 生成 L-erythro-2-ethoxy-3-methoxy-butane
  参考文献：
  名称：

  Stereochemistry of the Reaction of 2,3-Epoxybutane with Alcohols

  摘要：

  DOI：

  10.1021/ja01124a024
• 作为产物：
  描述：

  3-methoxybutan-2-one 在 Pt/Al₂O₃ 、 (-)-4-[(R)-((2S)-5-ethyl-1-azabicyclo[2.2.2]oct-2-yl)-methoxy-methyl]-quinoline 氢气 作用下， 以 溶剂黄146 为溶剂， 25.0 ℃ 、6.0 MPa 条件下， 反应 0.2h， 以20%的产率得到(+)-(2R,3S)-3-methoxy-2-butanol
  参考文献：
  名称：

  Hydrogenation of α-Keto Ethers: Dynamic Kinetic Resolution with a Heterogeneous Modified Catalyst and a Heterogeneous Base

  摘要：

  The first successful example of the asymmetric hydrogenation of substituted a-keto ethers with Cinchona-modified Pt/Al2O3 is reported. In the absence of an additional base, kinetic resolution of the racemic starting material was observed with high diastereoselectivity and ee's up to 98% at conversions of < 50%. Addition of KOH gave a strong reaction acceleration but racemic product. Immobilization of OH- on solid ion exchangers resulted in the desired dynamic kinetic resolution, and ee's of > 80% were obtained at > 95% conversion. These effects are rationalized on the basis of a simple kinetic and structural model.

  DOI：

  10.1002/1615-4169(200207)344:5<511::aid-adsc511>3.0.co;2-d

文献信息

• Enantioselektive Reaktionen an porphinoiden Nickelkomplexen
  作者：Kurt Meier、Rolf Scheffold

  DOI：10.1002/hlca.19810640526

  日期：1981.7.22

  Enantioselective Reactions on Porphine Type Nickel Complexes

  卟啉型镍配合物的对映选择性反应
• Asymmetric hydroboration of [ E ]- and [ Z ]-2-methoxy-2-butenes. Synthesis of (−)-[2 R ,3 R ]-butane-2,3-diol in &gt;97% ee
  作者：Dhanabalan Murali、Bakthan Singaram、Herbert C. Brown

  DOI：10.1016/s0957-4166(00)00485-7

  日期：2000.12

  Asymmetric hydroboration of [E]- and [Z]-2-methoxy-2-butene, using (-)-diisopinocampheylborane at -25 degreesC in THF solvent, followed by oxidation using H2O2/NaOH, gave (-)-[2R,3R]- and (+)-[2R,3S]-3-methoxy-2-butanols in >97 and 90% ee, respectively. (-)-[2R,3R]-3-Methoxy-2-butanol was converted to (-)-[2R,3R]-butane-2,3-diol (>97% ee, in an overall yield of 65%). (C) 2001 Elsevier Science Ltd. All rights reserved.
• Winstein; Henderson, Journal of the American Chemical Society, 1943, vol. 65, p. 2199
  作者：Winstein、Henderson

  DOI：——

  日期：——
• Shvets,V.F. et al., Journal of Organic Chemistry USSR (English Translation), 1971, vol. 7, p. 1920 - 1924
  作者：Shvets,V.F. et al.

  DOI：——

  日期：——
• Hydrogenation of α-Keto Ethers: Dynamic Kinetic Resolution with a Heterogeneous Modified Catalyst and a Heterogeneous Base
  作者：Martin Studer、Hans-Ulrich Blaser、Stephan Burkhardt

  DOI：10.1002/1615-4169(200207)344:5<511::aid-adsc511>3.0.co;2-d

  日期：2002.7

  The first successful example of the asymmetric hydrogenation of substituted a-keto ethers with Cinchona-modified Pt/Al2O3 is reported. In the absence of an additional base, kinetic resolution of the racemic starting material was observed with high diastereoselectivity and ee's up to 98% at conversions of < 50%. Addition of KOH gave a strong reaction acceleration but racemic product. Immobilization of OH- on solid ion exchangers resulted in the desired dynamic kinetic resolution, and ee's of > 80% were obtained at > 95% conversion. These effects are rationalized on the basis of a simple kinetic and structural model.