ethyl 2-(5-(3-bromophenyl)-2,4-bis(hydroxymethyl)cyclopent-1-en-1-yl)acetate | 1394173-71-7

• 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: ethyl 2-(5-(3-bromophenyl)-2,4-bis(hydroxymethyl)cyclopent-1-en-1-yl)acetate
• 英文别名: ethyl 2-[(4R,5S)-5-(3-bromophenyl)-2,4-bis(hydroxymethyl)cyclopenten-1-yl]acetate
• CAS: 1394173-71-7
• 化学式: C₁₇H₂₁BrO₄
• 分子量: 369.255
• InChiKey: KHTAFNFXZKIVRH-SUMWQHHRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  ethyl 2-[5-(3-bromophenyl)-2,4-diformylcyclopenten-1-yl]acetate 在 sodium cyanoborohydride 、 溶剂黄146 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 ethyl 2-(5-(3-bromophenyl)-2,4-bis(hydroxymethyl)cyclopent-1-en-1-yl)acetate 、 ethyl 2-(5-(3-bromophenyl)-2,4-bis(hydroxymethyl)cyclopent-1-en-1-yl)acetate
  参考文献：
  名称：

  The combination of domino process and kinetic resolution: organocatalytic synthesis of functionalised cyclopentenes by sequential SN2′-Michael reaction

  摘要：

  An interesting combination of organocatalytic cascade reaction and kinetic resolution was developed for the synthesis of functionalised cyclopentenes by sequential S(N)2'-Michael process. Treatment of the racemic nitroallylic acetates with glutaraldehyde in the presence of diphenylprolinol silyl ether to give tetrasubstituted cyclopentenes with high to excellent stereoselectivities (up to 96% ee and 12:1 dr). The less reactive enantiomeric substrates were generally recovered with good to excellent optical purities (up to 99% ee). (C) 2012 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2012.06.085