(S)-4-(2-hydroxy-3,3-dimethyl-4-p-tolyl-butyl)benzaldehyde | 647033-35-0

• 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)-4-(2-hydroxy-3,3-dimethyl-4-p-tolyl-butyl)benzaldehyde
• 英文别名: Benzaldehyde, 4-[(2S)-2-hydroxy-3,3-dimethyl-4-(4-methylphenyl)butyl]-；4-[(2S)-2-hydroxy-3,3-dimethyl-4-(4-methylphenyl)butyl]benzaldehyde
• CAS: 647033-35-0
• 化学式: C₂₀H₂₄O₂
• 分子量: 296.409
• InChiKey: LPZPUGIDIJZJQB-IBGZPJMESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  对溴苯甲醛 、 3,3-dimethyl-4-(4-methylphenyl)-1-butene 在 (bicyclo[2.2.1]hepta-2,5-diene)-(2,4-pentanedionato)-rhodium 、 双联邻苯二酚硼酸酯 、 1-(2-二苯基庚基1萘酚)硫酸甲基酯 、 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 caesium carbonate 、 sodium hydroxide 、 双氧水 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 30.0h， 以48%的产率得到(S)-4-(2-hydroxy-3,3-dimethyl-4-p-tolyl-butyl)benzaldehyde
  参考文献：
  名称：

  Catalytic Asymmetric Carbohydroxylation of Alkenes by a Tandem Diboration/Suzuki Cross-Coupling/Oxidation Reaction

  摘要：

  Chiral nonsymmetric 1,2-diboron adducts are generated by catalytic enantioselective diboration. Oxidation of these adducts provides 1,2-diols in good yield. Alternatively, 1,2-diboron compounds may be reacted, in situ, with aryl halides wherein the less hindered C-B bond participates in cross-coupling. The remaining C-B bond is then oxidized in the reaction workup thereby allowing for net asymmetric carbohydroxylation of alkenes in a tandem one-pot diboration/Suzuki coupling/oxidation sequence.

  DOI：

  10.1021/ol036219a

文献信息

• [EN] CATALYZED ENANTIOSELECTIVE TRANSFORMATION OF ALKENES<br/>[FR] TRANSFORMATION ENANTIO-SELECTIVE CATALYSEE D'ALCENES
  申请人：UNIV NORTH CAROLINA

  公开号：WO2005012209A3

  公开（公告）日：2005-08-11
• Catalytic Asymmetric Carbohydroxylation of Alkenes by a Tandem Diboration/Suzuki Cross-Coupling/Oxidation Reaction
  作者：Steven P. Miller、Jeremy B. Morgan、Nepveux、James P. Morken

  DOI：10.1021/ol036219a

  日期：2004.1.1

  Chiral nonsymmetric 1,2-diboron adducts are generated by catalytic enantioselective diboration. Oxidation of these adducts provides 1,2-diols in good yield. Alternatively, 1,2-diboron compounds may be reacted, in situ, with aryl halides wherein the less hindered C-B bond participates in cross-coupling. The remaining C-B bond is then oxidized in the reaction workup thereby allowing for net asymmetric carbohydroxylation of alkenes in a tandem one-pot diboration/Suzuki coupling/oxidation sequence.