(S)-3,5-Diphenyl-5-oxopentanoic acid | 174814-83-6

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物
• 英文名称: (S)-3,5-Diphenyl-5-oxopentanoic acid
• 英文别名: (S)-5-oxo-3,5-diphenylpentanoic acid；(3S)-5-oxo-3,5-diphenylpentanoic acid
• CAS: 174814-83-6
• 化学式: C₁₇H₁₆O₃
• 分子量: 268.312
• InChiKey: ZOKVLFUFXBUTKQ-HNNXBMFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-3,5-Diphenyl-5-oxopentanoic acid 在 草酰氯 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以93%的产率得到(R)-4,6-diphenyl-3,4-dihydro-2H-pyran-2-one
  参考文献：
  名称：

  手性季铵盐催化的高度对映选择性迈克尔反应。通过（S）-鸟氨酸和手性2-环己烯酮的不对称合成进行说明。

  摘要：

  [分子式：见正文]手性季铵盐1a和1b的使用使对映选择性Michael反应成为可能，该反应已应用于（S）-鸟氨酸（2）和手性2-环己烯酮6的不对称合成。

  DOI：

  10.1021/ol0056527
• 作为产物：
  描述：

  (3R,5R,9R)-3,7,9-triphenyl-1,4,6-trioxaspiro[4.5]dec-7-ene 在 氢氧化钾 、 acid ion-exchange resin 、 四丁基溴化铵 作用下， 生成 (S)-3,5-Diphenyl-5-oxopentanoic acid
  参考文献：
  名称：

  Transformations of isoxazolidine and dihydropyran derivatives to optically active compounds

  摘要：

  Isoxazolidine and dihydropyran spiro derivatives can be easily transformed, by hydrolysis and hydrogenolysis, to give delta-keto esters, delta-keto acids, beta-amino esters, beta-amino acids and 3-amino alcohols in good yields, Starting from optically active compounds enantiomerically pure products are obtained, In some cases, reactions were induced by microwave irradiation.

  DOI：

  10.1039/p19960000259

文献信息

• Enantioselective Mukaiyama-Michael Reaction of Silyl Enol Ethers to 2-Enoylpyridine<i>N</i>-Oxides Catalyzed by Copper- Bis(oxazoline) Complex
  作者：Jimil George、Basi V. Subba Reddy

  DOI：10.1002/adsc.201200631

  日期：2013.1.16

  A catalytic enantioselective Mukaiyama–Michael reaction of 2-enoylpyridine N-oxides has been developed using a simple bis(oxazoline)-copper complex. A variety of silyl enol ethers undergo smooth Michael addition with 2-enoylpyridine N-oxides to furnish the corresponding Michael adducts in high yields with high enantioselectivities (up to 97% ee).

  使用简单的双（恶唑啉）-铜配合物开发了2-烯丙基吡啶N-氧化物的催化对映选择性Mukaiyama-Michael反应。各种甲硅烷基烯醇醚与2-烯丙基吡啶N-氧化物进行平滑的迈克尔加成反应，以高收率和高对映选择性（高达97％ee）提供相应的迈克尔加合物。
• Diphenylprolinol Silyl Ether as a Catalyst in an Enantioselective, Catalytic, Formal Aza [3+3] Cycloaddition Reaction for the Formation of Enantioenriched Piperidines
  作者：Yujiro Hayashi、Hiroaki Gotoh、Ryouhei Masui、Hayato Ishikawa

  DOI：10.1002/anie.200800662

  日期：2008.5.13
• Ligand differentiated complementary Rh-catalyst systems for the enantioselective desymmetrization of meso-cyclic anhydrides
  作者：Jeffrey B. Johnson、Matthew J. Cook、Tomislav Rovis

  DOI：10.1016/j.tet.2008.10.075

  日期：2009.4

  Two distinct systems for the rhodium-catalyzed enantioselective desymmetrization of meso-cyclic anhydrides have been developed. Each system has been optimized and are compatible with the use of in situ prepared organozinc reagents. Rhodium/PHOX species efficiently catalyze the addition of alkyi nucleophiles to glutaric anhydrides, while system is effective in the enantioselective arylation of succinic and glutaric anhydrides. (C) 2008 Elsevier Ltd. All rights reserved.
• N-Heterocyclic Carbene Catalyzed CC Bond Cleavage in Redox Esterifications of Chiral Formylcyclopropanes
  作者：Stephanie S. Sohn、Jeffrey W. Bode

  DOI：10.1002/anie.200601919

  日期：2006.9.11
• Highly Enantioselective Desymmetrization of Anhydrides by Carbon Nucleophiles: Reactions of Grignard Reagents in the Presence of (−)-Sparteine
  作者：Ryo Shintani、Gregory C. Fu

  DOI：10.1002/1521-3773(20020315)41:6<1057::aid-anie1057>3.0.co;2-h

  日期：2002.3.15