(2S,3S)-anti-2-methyl-1-phenyl-3-hydroxy-1-butanone | 115936-18-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,3S)-anti-2-methyl-1-phenyl-3-hydroxy-1-butanone
• 英文别名: (2S,3S)-3-hydroxy-2-methyl-1-phenylbutan-1-one；(2S,3S)-3-hydroxy-2-methyl-1-phenylbutanone
• CAS: 115936-18-0
• 化学式: C₁₁H₁₄O₂
• 分子量: 178.231
• InChiKey: LZWQBCUNLJNOPL-IUCAKERBSA-N

物化性质

• 熔点：
  43-45 °C
• 沸点：
  301.7±25.0 °C(Predicted)
• 密度：
  1.056±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2S,3S)-anti-2-methyl-1-phenyl-3-hydroxy-1-butanone 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 以21%的产率得到(1S,2S,3S)-2-methyl-1-phenyl-1,3-butanediol
  参考文献：
  名称：

  A chemo-enzymatic route to diastereoisomers of 2-methyl-1-phenyl-1,3-butanediol: the dual role of microorganisms

  摘要：

  Diastereoisomers (1S,2R,3S)-, (1R,2R,3S)-, (IR,2S,3S)- and (1S,2S,3S)-2-methyl-1-phenyl-1,3-butanediols were prepared by simple and convenient strategies using two different chemo-enzymatic approaches for the reduction of racemic 2-methyl-1-phenyl-1, 3-butanedione, both involving in situ racemization. The first method comprised a one-pot microbial reduction coupled with a chemical reduction, while in the second method, stepwise chemo-enzymatic reductions were performed. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.10.045
• 作为产物：
  描述：

  (2RS,3S)-3-hydroxy-2-methyl-1-phenylbutan-1-one 在 manganese(IV) oxide 、 sodium tetrahydroborate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 24.0h， 生成 (2S,3S)-anti-2-methyl-1-phenyl-3-hydroxy-1-butanone
  参考文献：
  名称：

  手性和香气化学：商业手性气味Muguesia和Pamplefleur的立体异构体

  摘要：

  这项工作描述了商业气味剂Muguesia和Pamplefleur的单一立体异构体的酶介导的制备和气味评估。Muguesia立体异构体的合成方法有助于清除中间二醇5的相对构型的分配。发现潘普洛夫尔异构体的气味响应是非常不寻常的。没有立体异构体占主导地位，但每个异构体在确定最终混合物的气味感方面起着确定的作用。

  DOI：

  10.1021/jo048445j

文献信息

• Catalytic asymmetric synthesis of β-hydroxy ketones by palladium-catalyzed asymmetric 1,4-disilylation of α,β-unsaturated ketones
  作者：Yonetatsu Matsumoto、Tamio Hayashi、Yoshihiko Ito

  DOI：10.1016/s0040-4020(01)80758-4

  日期：1994.1

  1,4-Disilylation of β,β-unsaturated ketones with 1,1-dichloro-l-phenyl-2,2,2-trimethyldisilane proceeded in the presence of phosphine-palladium catalysts in benzene. High enantio-selectivity (up to 92%) was observed in the disilylation with dichloro[(R)-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl]palladium(II) as a catalyst (0.5 mol %). The disilylation products, 1-(trimethyisilyloxy)-3-(dichlorophenylsilyl)propenes

  在苯存在膦-钯催化剂的情况下，将β，β-不饱和酮与1,1-二氯-1-苯基-2,2,2-三甲基乙硅烷进行1,4-二甲化。使用二氯[（R）-2,2'-双（二苯基膦基）-1,1'-联萘]钯（II）（0.5 mol％ ）。容易将二甲硅烷基化产物1-（三甲基甲硅烷基氧基）-3-（二氯苯基甲硅烷基）丙烯转化为旋光性的α-未取代或抗α-取代的β-（苯基二甲基甲硅烷基）酮，其氧化反应生成相应的旋光性β-羟基酮高产。
• Synthesis of Valuable Chiral Intermediates by Isolated Ketoreductases: Application in the Synthesis of α-Alkyl-β-hydroxy Ketones and 1,3-Diols
  作者：Dimitris Kalaitzakis、J. David Rozzell、Ioulia Smonou、Spiros Kambourakis

  DOI：10.1002/adsc.200606185

  日期：2006.9

  and in two examples both ketones were reduced to the 1,3-diol. By replacing the α-alkyl substituent with the OAc group, 1-keto-2,3-diols, as well as 1,2,3-triols were synthesized in high optical purities. These enzymatic reactions provide a simple, highly stereoselective and quantitative method for the synthesis of different diastereomers of valuable chiral synthons from non-chiral, easily accessible

  描述了通过使用可商购的酮还原酶（KRED）将α-取代的1，3-二酮区域和立体选择性还原为相应的β-酮醇或1，3-二醇。在一个或两个酶促还原步骤中，许多α-单烷基或二烷基取代的对称及非对称二酮的高光学纯度和化学收率得到降低。在大多数情况下，通过使用不同的酶来合成四种可能的α-烷基-β-酮醇非对映异构体中的两个甚至三个，并且在两个实例中，两种酮均还原为1,3-二醇。通过用OAc基团取代α-烷基取代基，可以以高光学纯度合成1-酮-2,3-二醇以及1,2,3-三醇。这些酶促反应提供了一种简单，
• Enantioselective Monoreduction of 2-Alkyl-1,3-diketones Mediated by Chiral Ruthenium Catalysts. Dynamic Kinetic Resolution
  作者：Florence Eustache、Peter I. Dalko、Janine Cossy

  DOI：10.1021/ol025527q

  日期：2002.4.1

  The reduction of 2-alkyl-1,3-diketones using (R,R)- or (S,S)-RuCl[N-(tosyl)-1,2-diphenylethylenediamine](p-cymene) in the presence of formic acid and triethylamine affords syn-2-alkyl-3-hydroxy ketones as the major products with high enantioselectivity. [reaction: see text]

  在存在甲酸的情况下，使用（R，R）-或（S，S）-RuCl [N-（甲苯磺酰基）-1,2-二苯基乙二胺]（对伞花烯）还原2-烷基-1,3-二酮酸和三乙胺可提供对位-2-烷基-3-羟基酮作为主要产物，具有高对映选择性。[反应：看文字]
• Palladium-catalyzed asymmetric 1,4-disilylation of .alpha.,.beta.-unsaturated ketones: catalytic asymmetric synthesis of .beta.-hydroxy ketones
  作者：Tamio. Hayashi、Yonetatsu. Matsumoto、Yoshihiko. Ito

  DOI：10.1021/ja00224a057

  日期：1988.8
• A chemo-enzymatic route to diastereoisomers of 2-methyl-1-phenyl-1,3-butanediol: the dual role of microorganisms
  作者：K. Ahmad、S.C. Taneja、A.P. Singh、N. Anand、M.A. Qurishi、S. Koul、G.N. Qazi

  DOI：10.1016/j.tet.2006.10.045

  日期：2007.1

  Diastereoisomers (1S,2R,3S)-, (1R,2R,3S)-, (IR,2S,3S)- and (1S,2S,3S)-2-methyl-1-phenyl-1,3-butanediols were prepared by simple and convenient strategies using two different chemo-enzymatic approaches for the reduction of racemic 2-methyl-1-phenyl-1, 3-butanedione, both involving in situ racemization. The first method comprised a one-pot microbial reduction coupled with a chemical reduction, while in the second method, stepwise chemo-enzymatic reductions were performed. (c) 2006 Elsevier Ltd. All rights reserved.