(-)-(2S,3S)-4-phenyl-2,3-epoxybutane | 158703-51-6

• 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: (-)-(2S,3S)-4-phenyl-2,3-epoxybutane
• 英文别名: (2S,3S)-2-benzyl-3-methyloxirane
• CAS: 158703-51-6
• 化学式: C₁₀H₁₂O
• 分子量: 148.205
• InChiKey: QMIJGRJEXQYRJV-WPRPVWTQSA-N

物化性质

• 沸点：
  215.0±9.0 °C(Predicted)
• 密度：
  1.039±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  12.5
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (-)-(2S,3S)-4-phenyl-2,3-epoxybutane 在 lithium aluminium tetrahydride 、 sodium azide 、 氯化铵 作用下， 以 甲醇 、 乙醚 、 水 为溶剂， 反应 3.0h， 生成 (+)-(2S,3R)-3-amino-4-phenyl-2-butanol
  参考文献：
  名称：

  Chemoenzymatic synthesis of chiral β-azidoalcohols. Application to the preparation of chiral aziridines and aminoalcohols

  摘要：

  From the microbiological reduction of 3-azido-2-octanone, 3-azido-4-phenyl-2-butanone and 1-azido-1-phenyl-2-propanone, homochiral isomers of the corresponding beta-azidoalcohols were prepared. These ''alpha-bichiral'' synthons were used to prepare all the stereoisomers of 2-methyl-3-n-pentylaziridine and 2-methyl-3-benzylaziridine and some homochiral aminoalcohols.

  DOI：

  10.1016/0957-4166(94)80084-7
• 作为产物：
  描述：

  3-溴-4-苯基-2-丁酮 在 sodium ethanolate 作用下， 以 甲醇 为溶剂， 反应 24.0h， 生成 (-)-(2S,3S)-4-phenyl-2,3-epoxybutane
  参考文献：
  名称：

  Chemoenzymatic synthesis of chiral epoxides. Preparation of 4-phenyl-2,3-epoxybutane and 1-phenyl-1,2-epoxypropane

  摘要：

  All the stereoisomers of 4-phenyl-2,3-epoxybutane and 1-phenyl-1,2-epoxypropane (beta-methylstyrene oxide) have been prepared in three steps from 4-phenyl-2-butanone and 1-phenyl-2-propanone or 1-phenyl-1-propanone respectively. The key step is the microbiological reduction of the corresponding haloketones. These results confirm those previously described(1) and demonstrate that the chemoenzymatic synthesis of homochiral 2,3-epoxides is a general method that can be used whatever the starting ketone.

  DOI：

  10.1016/0957-4166(94)80167-3

文献信息

• Molecular design of thermostable alcohol dehydrogenase for synthesis for chiral aromatic alcohols
  申请人：Zeikus J. Gregory

  公开号：US20080220487A1

  公开（公告）日：2008-09-11

  The present invention relates to compositions and methods utilizing thermostable and novel alcohol dehydrogenase enzymes for biosynthesizing chiral specific molecules for use as precursor molecules in synthesizing pharmaceutical compounds. Particularly, in preferred embodiments, the invention relates to directed engineering of an enzymatic catalytic site of an alcohol dehydrogenase enzyme gene for enhancing enantioselectivity for (S)-enantiomer substrate catalytic activity for providing aryl (S)-enantiomer products in stereomeric excess.

  本发明涉及利用耐热和新型醇脱氢酶酶的组合物和方法，用于生物合成手性特异分子，作为合成药物化合物的前体分子。特别地，在优选实施例中，本发明涉及对醇脱氢酶酶基因的酶催化位点进行定向工程，以增强对(S)-对映体底物的对映选择性催化活性，从而提供(S)-对映体产物的立体过量。
• Regioselective Carbonylation of <i>trans</i>-Disubstituted Epoxides to β-Lactones: A Viable Entry into <i>syn</i>-Aldol-Type Products
  作者：Michael Mulzer、Bryan T. Whiting、Geoffrey W. Coates

  DOI：10.1021/ja405151n

  日期：2013.7.31

  reported for the regioselective carbonylation of trans-disubstituted epoxides to cis-β-lactones. The two catalysts display high and opposing selectivities, which generally are difficult to achieve for this class of epoxides. The resulting β-lactones are well-defined precursors for a wide variety of aldol-type compounds. Altogether, carbonylation of disubstituted epoxides is established as a viable and

  据报道，两种新催化剂可用于将反式双取代环氧化物区域选择性羰基化成顺式-β-内酯。这两种催化剂显示出高且相反的选择性，这对于此类环氧化物通常难以实现。由此产生的 β-内酯是各种羟醛型化合物的明确前体。总之，双取代环氧化物的羰基化被确立为合成和抗羟醛产品的可行且经济的入口。
• US7750135B2
  申请人：——

  公开号：US7750135B2

  公开（公告）日：2010-07-06
• Chemoenzymatic synthesis of chiral epoxides. Preparation of 4-phenyl-2,3-epoxybutane and 1-phenyl-1,2-epoxypropane
  作者：Pascale Besse、Michel F. Renard、Henri Veschambre

  DOI：10.1016/0957-4166(94)80167-3

  日期：1994.7

  All the stereoisomers of 4-phenyl-2,3-epoxybutane and 1-phenyl-1,2-epoxypropane (beta-methylstyrene oxide) have been prepared in three steps from 4-phenyl-2-butanone and 1-phenyl-2-propanone or 1-phenyl-1-propanone respectively. The key step is the microbiological reduction of the corresponding haloketones. These results confirm those previously described(1) and demonstrate that the chemoenzymatic synthesis of homochiral 2,3-epoxides is a general method that can be used whatever the starting ketone.
• Chemoenzymatic synthesis of chiral β-azidoalcohols. Application to the preparation of chiral aziridines and aminoalcohols
  作者：Pascle Besse、Henri Veschambre、Robert Chênevert、Michael Dickman

  DOI：10.1016/0957-4166(94)80084-7

  日期：1994.9

  From the microbiological reduction of 3-azido-2-octanone, 3-azido-4-phenyl-2-butanone and 1-azido-1-phenyl-2-propanone, homochiral isomers of the corresponding beta-azidoalcohols were prepared. These ''alpha-bichiral'' synthons were used to prepare all the stereoisomers of 2-methyl-3-n-pentylaziridine and 2-methyl-3-benzylaziridine and some homochiral aminoalcohols.