(2R,3S)-3-cyclohexyl-1-(2-ethyl-1H-pyrrol-1-yl)-2,3-dihydroxypropan-1-one | 1449799-08-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: (2R,3S)-3-cyclohexyl-1-(2-ethyl-1H-pyrrol-1-yl)-2,3-dihydroxypropan-1-one
• 英文别名: (2R,3S)-3-cyclohexyl-1-(2-ethylpyrrol-1-yl)-2,3-dihydroxypropan-1-one
• CAS: 1449799-08-9
• 化学式: C₁₅H₂₃NO₃
• 分子量: 265.353
• InChiKey: LCMIRKZFRXTLLL-UONOGXRCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  62.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2R,3S)-3-cyclohexyl-1-(2-ethyl-1H-pyrrol-1-yl)-2,3-dihydroxypropan-1-one 在 对甲苯磺酸 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 1.25h， 生成 ((4S,5S)-5-cyclohexyl-2,2-dimethyl-1,3-dioxolan-4-yl)methanol
  参考文献：
  名称：

  Dinuclear Zinc–ProPhenol-Catalyzed Enantioselective α-Hydroxyacetate Aldol Reaction with Activated Ester Equivalents

  摘要：

  An enantioselective alpha-hydroxyacetate aldol reaction that employs N-acetyl pyrroles as activated ester equivalents and generates syn 1,2-diols in good yield and diastereoselectivity is reported. This dinuclear zinc-ProPhenol-catalyzed transformation proceeds with high enantioselectivity with a wide variety of substrates including aryl, alyl, and alkenyl aldehydes. The resulting alpha,beta-dihydroxy activated esters are versatile intermediates for the synthesis of a variety of carboxylic acid derivatives including amides, esters, and unsymmetrical ketones.

  DOI：

  10.1021/ol402081p
• 作为产物：
  描述：

  2-乙基吡咯 在 正丁基锂 、 (R,R)-(-)-2,6-bis[2-(hydroxyldiphenylmethyl)-1-pyrrolidinyl-methyl]-4-methylphenole 、 diethylzinc 、 三溴化硼 作用下， 以 四氢呋喃 、 正己烷 、 正庚烷 、 二氯甲烷 为溶剂， 反应 73.0h， 生成 (2R,3S)-3-cyclohexyl-1-(2-ethyl-1H-pyrrol-1-yl)-2,3-dihydroxypropan-1-one 、 3-cyclohexyl-1-(2-ethyl-1H-pyrrol-1-yl)-2,3-dihydroxypropan-1-one
  参考文献：
  名称：

  Dinuclear Zinc–ProPhenol-Catalyzed Enantioselective α-Hydroxyacetate Aldol Reaction with Activated Ester Equivalents

  摘要：

  An enantioselective alpha-hydroxyacetate aldol reaction that employs N-acetyl pyrroles as activated ester equivalents and generates syn 1,2-diols in good yield and diastereoselectivity is reported. This dinuclear zinc-ProPhenol-catalyzed transformation proceeds with high enantioselectivity with a wide variety of substrates including aryl, alyl, and alkenyl aldehydes. The resulting alpha,beta-dihydroxy activated esters are versatile intermediates for the synthesis of a variety of carboxylic acid derivatives including amides, esters, and unsymmetrical ketones.

  DOI：

  10.1021/ol402081p

文献信息

• Dinuclear Zinc–ProPhenol-Catalyzed Enantioselective α-Hydroxyacetate Aldol Reaction with Activated Ester Equivalents
  作者：Barry M. Trost、David J. Michaelis、Mihai I. Truica

  DOI：10.1021/ol402081p

  日期：2013.9.6

  An enantioselective alpha-hydroxyacetate aldol reaction that employs N-acetyl pyrroles as activated ester equivalents and generates syn 1,2-diols in good yield and diastereoselectivity is reported. This dinuclear zinc-ProPhenol-catalyzed transformation proceeds with high enantioselectivity with a wide variety of substrates including aryl, alyl, and alkenyl aldehydes. The resulting alpha,beta-dihydroxy activated esters are versatile intermediates for the synthesis of a variety of carboxylic acid derivatives including amides, esters, and unsymmetrical ketones.