(3R,4S)-4-(1-bromonaphthalen-2-yl)-3,4-dihydroxybutan-2-one

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (3R,4S)-4-(1-bromonaphthalen-2-yl)-3,4-dihydroxybutan-2-one
• 化学式: C₁₄H₁₃BrO₃
• 分子量: 309.159
• InChiKey: DNYHDTPJQRKIAV-KBPBESRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1-溴-2-萘甲醛 、 羟基丙酮 在 L-Leu-NH[(S)-1-OH-1,1-(3,5-(CF₃)2C₆H₃)2-3-Me-butan-2-yl] 作用下， 以 xylene 为溶剂， 反应 48.0h， 生成 (3S,4R)-4-(1-bromonaphthalen-2-yl)-3,4-dihydroxybutan-2-one 、 (3R,4S)-4-(1-bromonaphthalen-2-yl)-3,4-dihydroxybutan-2-one 、 4-(1-bromonaphthalen-2-yl)-3,4-dihydroxybutan-2-one
  参考文献：
  名称：

  Design of Organocatalysts for Asymmetric Direct Syn-Aldol Reactions

  摘要：

  Two new organocatalysts 3a and 3b, derived from L-leucine and (S)-beta-amino alcohols that were prepared from L-valine, were designed and afforded the direct syn-aldol reactions of a wide scope of aldehydes with various ketones with an excellent diastereomeric ratio of up to >20/1 and enantioselectivities of up to 99% ee.

  DOI：

  10.1021/ol701798x

文献信息

• Design of Organocatalysts for Asymmetric Direct Syn-Aldol Reactions
  作者：Xiao-Ying Xu、Yan-Zhao Wang、Liu-Zhu Gong

  DOI：10.1021/ol701798x

  日期：2007.10.1

  Two new organocatalysts 3a and 3b, derived from L-leucine and (S)-beta-amino alcohols that were prepared from L-valine, were designed and afforded the direct syn-aldol reactions of a wide scope of aldehydes with various ketones with an excellent diastereomeric ratio of up to >20/1 and enantioselectivities of up to 99% ee.