(R)-3,4-bis(benzyloxy)butan-2-one | 94278-74-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (R)-3,4-bis(benzyloxy)butan-2-one
• 英文别名: (3R)-3,4-bis(phenylmethoxy)butan-2-one
• CAS: 94278-74-7
• 化学式: C₁₈H₂₀O₃
• 分子量: 284.355
• InChiKey: FFZWHYNJLAXXRN-GOSISDBHSA-N

物化性质

• 沸点：
  423.0±35.0 °C(Predicted)
• 密度：
  1.097±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  21
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R)-3,4-bis(benzyloxy)butan-2-one 以88%的产率得到
  参考文献：
  名称：

  MEAD, K.;MACDONALD, T. L., J. ORG. CHEM., 1985, 50, N 3, 422-424

  摘要：

  DOI：
• 作为产物：
  描述：

  (R)-(+)-1,2-O-isopropylidene-butane-1,2,3-triol 在 四丙基高钌酸铵 、 N-甲基吗啉氧化物 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以2.21 g的产率得到(R)-3,4-bis(benzyloxy)butan-2-one
  参考文献：
  名称：

  Diastereoselective reduction of ketimines derived from (R)-3,4-dihydroxybutan-2-one: an alternative route to key intermediates for the synthesis of anticancer agent ES-285

  摘要：

  A simple and convenient procedure for the diastereoselective reduction of imines derived from (R)-3,4-dihydroxybutan-2-one is described. The use of sodium borohydride as a reducing agent in the reactions with pre-synthesised imines gave aminodiol derivatives with the appropriate stereochemistry for use as intermediates in the synthesis of anticancer agent ES-285. The aminodiols were isolated in ca. 62% yield. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.02.012

文献信息

• Diastereodifferentiation in SN2' additions of methylcuprates to nonracemic acyclic vinyloxiranes
  作者：James A. Marshall、Bruce E. Blough

  DOI：10.1021/jo00006a049

  日期：1991.3

  S(N)2' additions of Me2CuLi, MeCu(CN)Li, and Me2Cu(CN)Li2 to the 2S and 2R alkoxy cis-(Z)- and -(E)- vinyloxiranes 8, 9, 13, and 14 were examined as possible routes to acrylic subunits of polypropionate natural products. Highest antisyn ratios were found for the (2S)- and (2R)-hydroxy-(E)-vinyloxiranes 13a and 14a followed by the (2R)-MTM ether analogue 14c. In both cases Me2CuLi gave higher ratios than either of the cyanocuprates (> 99:1 vs 14:1 for 13a/13b and > 40:1 vs approximately 24:1 for 14c).
• Metal ion controlled addition to .alpha.,.beta.-dialkoxy carbonyl compounds
  作者：Keith Mead、Timothy L. Macdonald

  DOI：10.1021/jo00203a040

  日期：1985.2
• Diastereoselective reduction of ketimines derived from (R)-3,4-dihydroxybutan-2-one: an alternative route to key intermediates for the synthesis of anticancer agent ES-285
  作者：Ana C. Allepuz、Ramón Badorrey、María D. Díaz-de-Villegas、José A. Gálvez

  DOI：10.1016/j.tetasy.2010.02.012

  日期：2010.3

  A simple and convenient procedure for the diastereoselective reduction of imines derived from (R)-3,4-dihydroxybutan-2-one is described. The use of sodium borohydride as a reducing agent in the reactions with pre-synthesised imines gave aminodiol derivatives with the appropriate stereochemistry for use as intermediates in the synthesis of anticancer agent ES-285. The aminodiols were isolated in ca. 62% yield. (C) 2010 Elsevier Ltd. All rights reserved.
• MEAD, K.;MACDONALD, T. L., J. ORG. CHEM., 1985, 50, N 3, 422-424
  作者：MEAD, K.、MACDONALD, T. L.

  DOI：——

  日期：——