(2S,3R)-4-phenyl-2,3-epoxybutane | 158703-50-5

• 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,3R)-4-phenyl-2,3-epoxybutane
• 英文别名: (2R,3S)-2-benzyl-3-methyloxirane
• CAS: 158703-50-5
• 化学式: C₁₀H₁₂O
• 分子量: 148.205
• InChiKey: QMIJGRJEXQYRJV-WCBMZHEXSA-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,3R)-4-phenyl-2,3-epoxybutane 在 sodium azide 、 氯化铵 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 生成 (-)-(2R,3S)-2-methyl-3-benzylaziridine
  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,3R)-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

• Hydride transfer versus electron transfer in the reduction of 4-phenyl-3-halo-3-buten-2-ones mediated by Pichia stipitis
  作者：Dávila S. Zampieri、Luiz A. Zampieri、J. Augusto R. Rodrigues、Bruno R.S. de Paula、Paulo J.S. Moran

  DOI：10.1016/j.molcatb.2011.07.001

  日期：2011.11

  Reductions of (Z)-C6H5CHCXC(O)CH3 (X = Cl, Br) mediated by Pichia stipitis gave 4-phenylbutan-2-one through dehalogenation of intermediaries 3-halo-4-phenylbutan-2-one by an electron transfer mechanism. The addition of 1,3-dinitrobenzene avoids the dehalogenation and thus the corresponding (2S,3S)-halohydrins were obtained in excellent enantiomeric excesses by a hydride transfer mechanism. Irganox® 1010 and

  毕赤酵母介导的（Z）-C 6 H 5 CHCXC（O）CH 3（X = Cl，Br）的还原通过中间体3-卤代-4-苯基丁烷-2-酮的脱卤作用而得到4-苯基丁酮-2-酮。通过电子转移机制。1,3-二硝基苯的加入避免了脱卤作用，因此通过氢化物转移机理以极好的对映体过量获得了相应的（2 S，3 S）-卤代醇。IRGANOX ® 1010和1076也被用来抑制电子传递机制。所获得的卤代醇是获得旋光性环氧化物和氨基醇的重要手性结构单元。
• Carbonylative, Catalytic Deoxygenation of 2,3-Disubstituted Epoxides with Inversion of Stereochemistry: An Alternative Alkene Isomerization Method
  作者：Jessica R. Lamb、Aran K. Hubbell、Samantha N. MacMillan、Geoffrey W. Coates

  DOI：10.1021/jacs.0c02653

  日期：2020.4.29

  activated substrates to achieve appreciable conversion without side product formation. Motivated by stereoinvertive epoxide carbonylation reactions, we developed a two-step epoxidation/deoxygenation process that results in overall inversion of alkene stereochemistry. Unlike most deoxygenation systems, carbon monoxide was used as the terminal reductant, preventing difficult postreaction separations, given

  促进烯烃立体化学反转的反应是现代有机合成领域罕见的、广受欢迎的转化。尽管存在许多异构化反应，但大多数方法需要特定的、高度活化的底物来实现可观的转化，而不会形成副产物。在立体转化环氧化物羰基化反应的推动下，我们开发了一个两步环氧化/脱氧过程，导致烯烃立体化学的整体转化。与大多数脱氧系统不同，考虑到生成的二氧化碳副产物的气态性质，一氧化碳被用作终端还原剂，防止了困难的反应后分离。各种烷基取代的顺式和反式环氧化物可以分别还原为反式和顺式烯烃，立体定向性 > 99:1，产率高达 95%，
• Carbonylation of <i>cis</i>-Disubstituted Epoxides to <i>trans</i>-β-Lactones: Catalysts Displaying Steric and Contrasteric Regioselectivity
  作者：Michael Mulzer、Geoffrey W. Coates

  DOI：10.1021/jo501899e

  日期：2014.12.19

  trans-beta-Lactones are a versatile and useful class of compounds, but reliable methods for their direct synthesis are still limited. Addressing this problem, we present herein two catalysts for the regioselective carbonylation of cis-disubstituted epoxides. The two catalysts show high activities and opposing regioselectivities so that either one of the two possible beta-lactone regioisomers can be obtained selectively.
• On the baker's yeast mediated transformation of α-bromoenones. Synthesis of (1S,2R)-2-bromoindan-1-ol and (2S,3S)-3-bromo-4-phenylbutan-2-ol
  作者：Josephina Aleu、Giovanni Fronza、Claudio Fuganti、Valentina Perozzo、Stefano Serra

  DOI：10.1016/s0957-4166(98)00128-1

  日期：1998.5

  Fermenting baker's yeast converts alpha-bromo substituted enones 7 and 10 into enantiomerically pure (1S,2R)2-bromoindan-1-ol 3 and (2S,3S)-3-bromo-4-phenylbutan-2-ol 11, respectively, through the intermediacy of the corresponding saturated ketones. Structurally related 16 provides the (2R)-allylic alcohol 17 prevalently. (C) 1998 Elsevier Science Ltd. All rights reserved.
• ZADOK ELAZAR; RUBINRAUT SARA; MAZUR YEHUDA, J. ORG. CHEM., 52,(1987) N 3, 385-390
  作者：ZADOK ELAZAR、 RUBINRAUT SARA、 MAZUR YEHUDA

  DOI：——

  日期：——