(R)-3-hydroxy-2,2,4-trimethylpentanal | 1373138-67-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (R)-3-hydroxy-2,2,4-trimethylpentanal
• 英文别名: (3R)-3-hydroxy-2,2,4-trimethylpentanal
• CAS: 1373138-67-0
• 化学式: C₈H₁₆O₂
• 分子量: 144.214
• InChiKey: OZMMQWRIAMEIJS-SSDOTTSWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  10
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (R)-3-hydroxy-2,2,4-trimethylpentanal 在 4-二甲氨基吡啶 、 sodium tetrahydroborate 作用下， 以 二氯甲烷 、 异丙醇 为溶剂， 反应 10.0h， 生成 (R)-3-hydroxy-2,2,4-trimethylpentyl (S)-3,3,3-trifluoro-2-methoxy-2-phenylpropanoate
  参考文献：
  名称：

  Isoleucine-Catalyzed Direct Asymmetric Aldol Addition of Enolizable Aldehydes

  摘要：

  Isoleucine-catalyzed direct enantioselective aldol additions between enolizable aldehydes are reported. Intermediate acetal structures dictate the configurative outcome and were supported by a hydrogen bond. This direct isoleucine-catalyzed aldol addition represents a welcome complement to both proline- and histidine-catalyzed aldol additions of enolizable aldehydes.

  DOI：

  10.1021/ol300754n
• 作为产物：
  描述：

  (2S,3S)-2-((2R,4S,6R)-2,6-diisopropyl-5,5-dimethyl-1,3-dioxan-4-ylamino)-3-methylpentanoic acid 在 水 、 对甲苯磺酸 作用下， 以 甲醇 为溶剂， 反应 12.0h， 生成 (R)-3-hydroxy-2,2,4-trimethylpentanal
  参考文献：
  名称：

  Isoleucine-Catalyzed Direct Asymmetric Aldol Addition of Enolizable Aldehydes

  摘要：

  Isoleucine-catalyzed direct enantioselective aldol additions between enolizable aldehydes are reported. Intermediate acetal structures dictate the configurative outcome and were supported by a hydrogen bond. This direct isoleucine-catalyzed aldol addition represents a welcome complement to both proline- and histidine-catalyzed aldol additions of enolizable aldehydes.

  DOI：

  10.1021/ol300754n

文献信息

• Asymmetric Histidine-Catalyzed Cross-Aldol Reactions of Enolizable Aldehydes: Access to Defined Configured Quaternary Stereogenic Centers
  作者：Morris Markert、Ulf Scheffler、Rainer Mahrwald

  DOI：10.1021/ja907054y

  日期：2009.11.25

  A histidine-catalyzed asymmetric direct cross-aldol reaction of enolizable aldehydes is described. In contrast to proline, histidine is able to clearly differentiate the reactivity of various aldehydes. In addition, this approach provides access to syn-configured B-hydroxyaldehydes. Thus, by application of this new methodology, defined-configuration quaternary stereocenters can be constructed with ease. The utility of this method is demonstrated in several total syntheses of branched-chain carbohydrates.
• Isoleucine-Catalyzed Direct Asymmetric Aldol Addition of Enolizable Aldehydes
  作者：Kerstin Rohr、Rainer Mahrwald

  DOI：10.1021/ol300754n

  日期：2012.4.20

  Isoleucine-catalyzed direct enantioselective aldol additions between enolizable aldehydes are reported. Intermediate acetal structures dictate the configurative outcome and were supported by a hydrogen bond. This direct isoleucine-catalyzed aldol addition represents a welcome complement to both proline- and histidine-catalyzed aldol additions of enolizable aldehydes.