5-(S)-p-nitrophenyl-5-hydroxy-3-oxo-pentanoic acid methyl ester

• 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: 5-(S)-p-nitrophenyl-5-hydroxy-3-oxo-pentanoic acid methyl ester
• 英文别名: methyl (5S)-5-hydroxy-5-(4-nitrophenyl)-3-oxopentanoate
• 化学式: C₁₂H₁₃NO₆
• 分子量: 267.238
• InChiKey: GPKKDNZUUYTHRY-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  109
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  (S)-5-(4-Nitro-phenyl)-3-oxo-5-trimethylsilanyloxy-pentanoic acid methyl ester 在 三氟乙酸 作用下， 以 四氢呋喃 为溶剂， 生成 5-(S)-p-nitrophenyl-5-hydroxy-3-oxo-pentanoic acid methyl ester
  参考文献：
  名称：

  Enantioselective aldol condensation of 1,3-bis-(trimethylsilyloxy)-1-methoxy-buta-1,3-diene promoted by chiral Ti(IV)/BINOL complex

  摘要：

  Enantiomerically enriched delta-hydroxy-beta-ketoesters are easily available by aldol condensation of 1,3-bis-(trimethylsilyloxy)-1-methoxy-buta-1,3-diene in the presence of Ti(O-iPr)(4)/(S)-(-)-BINOL system. All reaction mixtures were separated by column chromatography and mostly isolated in moderate to good yields and all in high enantiomeric excesses. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(00)00200-7

文献信息

• 1-Naphthyl-TADDOL/Emim BF4: A new catalytic system for the asymmetric addition of Chan’s diene to aromatic aldehydes
  作者：Rosaria Villano、Maria Acocella、Vincenzo Sio、Arrigo Scettri

  DOI：10.2478/s11532-010-0100-5

  日期：2010.12.1

  A new organocatalytic system was tested as a promoter for the asymmetric addition of Chan’s diene to aldehydes under solvent-free conditions. This new organocatalyst generated in situ by mixing 1-naphthyl-TADDOL derivative and Emim BF4 was able to give enantioenriched vinylogous aldols and hetero-Diels-Alder cycloadducts. A mechanistic investigation through the detection of nonlinear effects confirmed

  测试了一种新的有机催化体系，作为在无溶剂条件下将Chan's二烯不对称加成到醛中的促进剂。通过将1-萘基-TADDOL衍生物和Emim BF 4混合原位生成的这种新的有机催化剂能够提供对映体富集的乙烯基醇醛醇和杂-Diels-Alder环加合物。通过检测非线性效应进行的机械研究证实了离子液体参与了新的催化超分子物质的形成。
• 一种手性β羟基1,3-二羰基类化合物的合成方法
  申请人：温州大学新材料与产业技术研究院

  公开号：CN112574041B

  公开（公告）日：2022-10-28

  本发明公开了一种利用过渡金属盐与手性配体催化普通羰基类化合物与1,3,‑丙酮二甲酸单酯类化合物直接发生脱羧加成反应，合成具有重要作用合成子的手性β羟基‑1，3‑二羰基类化合物的方法，该方法操作简单、成本低廉、反应收率高、具有高立体选择性。
• An efficient asymmetric aldol reaction of Chan's diene promoted by chiral Ti(IV)–BINOL complex
  作者：Annunziata Soriente、Margherita De Rosa、Marina Stanzione、Rosaria Villano、Arrigo Scettri

  DOI：10.1016/s0957-4166(01)00150-1

  日期：2001.4

  1.3-Bis-(trimethylsilyloxy)-1-methoxy-buta-1,3-diene (Chan's diene) can be conveniently used in asymmetric aldol reaction with aromatic, heteroaromatic, alpha,beta -unsaturated and aliphatic aldehydes in the presence of catalytic amounts (2-8% mol) of chiral Ti(IV)/(R)-BINOL complex. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Achiral additives dramatically enhance enantioselectivities in the BINOL–Ti(IV) complex catalyzed aldol condensations of aldehydes with Chan’s diene
  作者：Qinyao Xu、Jianghui Yu、Fengyan Han、Juan Hu、Weiping Chen、Liping Yang

  DOI：10.1016/j.tetasy.2010.01.008

  日期：2010.2

  Achiral additives can dramatically enhance the enantioselectivities in the BINOL-Ti(IV) complex catalyzed aldol condensations of aldehydes with Chan's diene. The best results were obtained by using 2.0 equiv of LiCl with respect to (S)-BINOL/Ti(Oi-Pr)(4) as the additive. In the presence of 4.0 mol % of LiCl and 2.0 mol % of BINOL/Ti(Oi-Pr)(4), all aldehydes tested gave delta-hydroxy-beta-ketoesters as almost pure single enantiomers. Moreover, the present catalyst system was highly effective on reducing the catalyst loadings to 0.1 mol %. Published by Elsevier Ltd.
• Solvent-free asymmetric vinylogous aldol reaction of Chan's diene with aromatic aldehydes catalyzed by hydrogen bonding
  作者：Rosaria Villano、Maria Rosaria Acocella、Antonio Massa、Laura Palombi、Arrigo Scettri

  DOI：10.1016/j.tet.2009.01.112

  日期：2009.7

  Chan's diene proved to react with aromatic aldehydes under organocatalytic conditions in presence of a chiral naphthyl-TADDOL derivative to give vinylogous aldols (up to 65% ee) with complete gamma-selectivity. A further process of hetero-Diels-Alder cycloaddition, leading to chiral pyran-4-one derivatives (up to 60% ee), was favoured by electron-withdrawing substituents on the aromatic ring. (C) 2009 Elsevier Ltd. All rights reserved.