4-hydroxymethyl-hexanal cyclohemiacetal | 10444-29-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: 4-hydroxymethyl-hexanal cyclohemiacetal
• 英文别名: 5-ethyl-tetrahydro-pyran-2-ol；5-Ethyloxan-2-ol
• CAS: 10444-29-8
• 化学式: C₇H₁₄O₂
• 分子量: 130.187
• InChiKey: INYGRIDYFYSHGY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-hydroxymethyl-hexanal cyclohemiacetal 在 甲基磺酰氯 作用下， 以 吡啶 为溶剂， 以59%的产率得到3-Ethyl-2,3-dihydro-γ-pyran
  参考文献：
  名称：

  Kocienski, Philip; Yeates, Clive, Journal of the Chemical Society. Perkin transactions I, 1985, p. 1879 - 1884

  摘要：

  DOI：
• 作为产物：
  描述：

  diethyl 2-(cyanomethyl)-2-ethylmalonate 在 氢氧化钾 、 钾硼氢 、 lithium chloride 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 生成 4-hydroxymethyl-hexanal cyclohemiacetal
  参考文献：
  名称：

  Colonge,J. et al., Bulletin de la Societe Chimique de France, 1966, p. 2005 - 2011

  摘要：

  DOI：

文献信息

• Single Stereodifferentiation Associated with Carbon Atom Insertion during the Oxonium Ion-Initiated Pinacol Rearrangement of Dihydrofuranyl and Dihydropyranyl Carbinols
  作者：Leo A. Paquette、James C. Lanter、Jeffrey N. Johnston

  DOI：10.1021/jo962019j

  日期：1997.3.1

  The stereoselectivity of the acid-promoted rearrangement of dihydrofuranyl and dihydropyranyl carbinols to spirocyclic ketones has been examined. These kinetically controlled isomerizations result in the ring expansion of the hydroxyl-substituted ring with generation of a newly stereogenic spirocyclic carbon atom. All of the adducts formed from several 4,5-dihydrofurans and cyclobutanone, cyclopentanone, and 2,2-dimethylcyclopentanone proved to be reactive. Of the 5,6-dihydropyrans examined, only the cyclobutanone adducts were sufficiently reactive to warrant study. The product distributions arising from the furanoid systems were characterized by modest discrimination in most cases. The more stereodifferentiating pyranoid systems show product distributions as high as 30:1. These results are explained in terms of transition state geometries (conformationally more flexible in the five-membered examples) while also taking into account the principle of stereoelectronic control.