3-methyl-2-phenylbutanal

• 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: 3-methyl-2-phenylbutanal
• 英文别名: (2S)-3-methyl-2-phenylbutanal
• 化学式: C₁₁H₁₄O
• 分子量: 162.232
• InChiKey: UKEXEDXJYSMZGZ-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  12
• 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：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-methyl-2-phenylbutanal 在 sodium tetrahydroborate 作用下， 以 甲醇 、 乙醚 、 甲苯 为溶剂， 反应 1.0h， 以111 mg的产率得到(S)-3-methyl-2-phenylbutan-1-ol
  参考文献：
  名称：

  Enantioselective α-Arylation of Aldehydes via the Productive Merger of Iodonium Salts and Organocatalysis

  摘要：

  The enantioselective alpha-arylation of aldehydes has been accomplished using diaiyliodonium salts and a combination of copper and organic catalysts. These mild catalytic conditions provide a new strategy for the enantioselective construction and retention of enolizable alpha-formyl benzylic stereocenters, a valuable synthon for the production of medicinal agents. As one example, this new asymmetric protocol has been applied to the rapid synthesis of (S)-ketoprofen, a commercially successful oral and topical analgesic.

  DOI：

  10.1021/ja2008906
• 作为产物：
  描述：

  二苯基碘三氟甲烷磺酸盐 、 异戊醛 在 (2R,5R)-2-tert-butyl-3-methyl-5-phenyl-4-imidazolidinone-trichloroacetic acid 、 碳酸氢钠 、 copper(I) bromide 作用下， 以 乙醚 、 甲苯 为溶剂， 反应 8.0h， 生成 3-methyl-2-phenylbutanal
  参考文献：
  名称：

  Enantioselective α-Arylation of Aldehydes via the Productive Merger of Iodonium Salts and Organocatalysis

  摘要：

  The enantioselective alpha-arylation of aldehydes has been accomplished using diaiyliodonium salts and a combination of copper and organic catalysts. These mild catalytic conditions provide a new strategy for the enantioselective construction and retention of enolizable alpha-formyl benzylic stereocenters, a valuable synthon for the production of medicinal agents. As one example, this new asymmetric protocol has been applied to the rapid synthesis of (S)-ketoprofen, a commercially successful oral and topical analgesic.

  DOI：

  10.1021/ja2008906

文献信息

• Isomerization of Terminal Epoxides by a [Pd–H] Catalyst: A Combined Experimental and Theoretical Mechanistic Study
  作者：Devendra J. Vyas、Evgeny Larionov、Céline Besnard、Laure Guénée、Clément Mazet

  DOI：10.1021/ja400325w

  日期：2013.4.24

  An unusual palladium hydride complex has been shown to be a competent catalyst in the isomerization of a variety of terminal and internal epoxides. The reaction displayed broad scope and synthetic utility. Experimental and theoretical evidence are provided for an unprecedented hydride mechanism characterized by two distinct enantio-determining steps. These results hold promise for the development of an enantioselective variant of the reaction.
• 10.1002/anie.202408418
  作者：Lainer, Bruno、Li, Shuailong、Mammadova, Flora、Dydio, Paweł

  DOI：10.1002/anie.202408418

  日期：——

  The conceptual merger of relay catalysis with dynamic kinetic resolution strategy is reported to enable regio‐ and enantioselective C(sp3)−H bond arylation of aliphatic alcohols, forming enantioenriched β‐aryl alcohols typically with >90:10 enantiomeric ratios (up to 98:2 er) and 36‐74% yields. The starting materials bearing neighbouring stereogenic centres can be converted to either diastereomer of the β‐aryl alcohol products, with >85:15 diastereomeric ratios determined by the catalysts. The reactions occur under mild conditions, ensuring broad compatibility, and involve readily available aryl bromides, an inorganic base, and commercial Ru‐ and Pd‐complexes. Mechanistic experiments support the envisioned mechanism of the transformation occurring through a network of regio‐ and stereoselective processes operated by a coherent Ru/Pd‐dual catalytic system.
• Enantioselective α-Arylation of Aldehydes via the Productive Merger of Iodonium Salts and Organocatalysis
  作者：Anna E. Allen、David W. C. MacMillan

  DOI：10.1021/ja2008906

  日期：2011.3.30

  The enantioselective alpha-arylation of aldehydes has been accomplished using diaiyliodonium salts and a combination of copper and organic catalysts. These mild catalytic conditions provide a new strategy for the enantioselective construction and retention of enolizable alpha-formyl benzylic stereocenters, a valuable synthon for the production of medicinal agents. As one example, this new asymmetric protocol has been applied to the rapid synthesis of (S)-ketoprofen, a commercially successful oral and topical analgesic.