3-(hydroxymethyl)-4-oxopentanal | 1246193-39-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-(hydroxymethyl)-4-oxopentanal
• CAS: 1246193-39-4
• 化学式: C₆H₁₀O₃
• 分子量: 130.144
• InChiKey: JGHPNZFTVGSLKF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.23
• 重原子数：
  9.0
• 可旋转键数：
  4.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  54.37
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  二氢-3-(三苯基膦亚基)-2(3H)-呋喃酮 、 3-(hydroxymethyl)-4-oxopentanal 以 二氯甲烷 为溶剂， 反应 20.0h， 以334 mg的产率得到3-(3-hydroxymethyl-4-oxo-pentylidene)-dihydro-furan-2-one
  参考文献：
  名称：

  A stereoselective cyclisation cascade mediated by SmI2–H2O: synthetic studies towards stolonidiol

  摘要：

  A cascade reaction involving sequential conjugate reduction, stereoselective aldol cyclisation and chemo-selective lactone reduction mediated by SmI2-H2O provides access to a cyclopentanol bearing two vicinal quaternary stereocentres with good stereocontrol. The functionalised cyclopentanol product has been converted to a key intermediate in ongoing asymmetric studies towards stolonidiol. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.03.047
• 作为产物：
  描述：

  3-(羟甲基)己-5-烯-2-酮 在 二甲基硫 、 臭氧 作用下， 以 二氯甲烷 为溶剂， 生成 3-(hydroxymethyl)-4-oxopentanal
  参考文献：
  名称：

  A stereoselective cyclisation cascade mediated by SmI2–H2O: synthetic studies towards stolonidiol

  摘要：

  A cascade reaction involving sequential conjugate reduction, stereoselective aldol cyclisation and chemo-selective lactone reduction mediated by SmI2-H2O provides access to a cyclopentanol bearing two vicinal quaternary stereocentres with good stereocontrol. The functionalised cyclopentanol product has been converted to a key intermediate in ongoing asymmetric studies towards stolonidiol. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.03.047

文献信息

• A stereoselective cyclisation cascade mediated by SmI2–H2O: synthetic studies towards stolonidiol
  作者：Thomas M. Baker、Lisa A. Sloan、Lokman H. Choudhury、Masahito Murai、David J. Procter

  DOI：10.1016/j.tetasy.2010.03.047

  日期：2010.5

  A cascade reaction involving sequential conjugate reduction, stereoselective aldol cyclisation and chemo-selective lactone reduction mediated by SmI2-H2O provides access to a cyclopentanol bearing two vicinal quaternary stereocentres with good stereocontrol. The functionalised cyclopentanol product has been converted to a key intermediate in ongoing asymmetric studies towards stolonidiol. (C) 2010 Elsevier Ltd. All rights reserved.