(R)-3-(4-chlorophenyl)-3-hydroxy-2,2-dimethylpropionaldehyde

• 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: (R)-3-(4-chlorophenyl)-3-hydroxy-2,2-dimethylpropionaldehyde
• 英文别名: 3-(4-chlorophenyl)-3-hydroxy-2,2-dimethylpropionaldehyde；(3R)-3-(4-chlorophenyl)-3-hydroxy-2,2-dimethylpropanal
• 化学式: C₁₁H₁₃ClO₂
• 分子量: 212.676
• InChiKey: LLPTWXIZJSRCQW-SNVBAGLBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  14
• 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

• 作为产物：
  描述：

  4-氯苯甲醛 、 异丁醛 在 (S)-C₆H₁₁SO₂NF₃ 作用下， 以 二甲基亚砜 为溶剂， 反应 96.0h， 生成 (R)-3-(4-chlorophenyl)-3-hydroxy-2,2-dimethylpropionaldehyde 、 (S)-3-(4-chlorophenyl)-3-hydroxy-2,2-dimethylpropionaldehyde
  参考文献：
  名称：

  Direct, pyrrolidine sulfonamide promoted enantioselective aldol reactions of α,α-dialkyl aldehydes: synthesis of quaternary carbon-containing β-hydroxy carbonyl compounds

  摘要：

  A procedure has been developed for direct, asymmetric aldol reactions of alpha,alpha-dialkyl aldehydes with aromatic aldehydes, which produces quaternary carbon-containing beta-hydroxy carbonyl compounds. The processes, promoted by the organocatalyst (S) pyrrolidine sulfonamide, take place in high yields with exceptionally high levels of enantioselectivities. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.05.067

文献信息

• Synthesis ofβ-Hydroxyaldehydes with Stereogenic Quaternary Carbon Centers by Direct Organocatalytic Asymmetric Aldol Reactions
  作者：Nobuyuki Mase、Fujie Tanaka、Carlos F. Barbas

  DOI：10.1002/anie.200353546

  日期：2004.4.26
• Biheteroaromatic diphosphine oxides-catalyzed stereoselective direct aldol reactions
  作者：Sergio Rossi、Maurizio Benaglia、Andrea Genoni、Tiziana Benincori、Giuseppe Celentano

  DOI：10.1016/j.tet.2010.11.009

  日期：2011.1

  A highly stereoselective direct aldol condensation of ketones to aromatic aldehydes was realized; the trichlorosilyl enolether generated in situ in the presence of tetrachlorosilane is activated by catalytic amounts of an enantiomerically pure biheteroaromatic phosphine oxide to react with aldehydes, coordinated as well as activated by the chiral cationic hypervalent silicon species. This Lewis acid-mediated Lewis base-catalyzed transformation allowed, starting from two carbonyl compounds, to directly synthesize beta-hydroxy ketones generally with high anti stereoselectivity and up to 93% ee for the anti isomer. (C) 2010 Elsevier Ltd. All rights reserved.