dodec-1-en-5-yn-4-ol | 5186-03-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: dodec-1-en-5-yn-4-ol
• 英文别名: Dodec-1-en-5-in-4-ol
• CAS: 5186-03-8
• 化学式: C₁₂H₂₀O
• 分子量: 180.29
• InChiKey: DPOODSICIXSFHX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  13
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  non-2-ynal 、 3-溴丙烯 在 tin(II) chloride dihdyrate 、 氢化铝 、 水 作用下， 以 四氢呋喃 为溶剂， 反应 0.08h， 以70%的产率得到dodec-1-en-5-yn-4-ol
  参考文献：
  名称：

  A practical procedure of low valent tin mediated Barbier allylation of aldehydes in wet solvent

  摘要：

  Use of aluminium as the reducing metal in spontaneous bimetal redox reaction has been elegantly exploited for allylation/crotylation of aldehydes in wet solvent. Here, low valent tin was prepared in situ by reduction of SnCl2 center dot 2H(2)O with aluminium in THF/water. The resulting low valent tin acted as an efficient mediator for allylation and crotylation of aldehydes (3a-q) producing the corresponding homoallylic alcohols. The efficacy of this procedure was due to its operational simplicity, practical viability, inexpensiveness, good yields of the products and short reaction time. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.09.096

文献信息

• Cr-waste free catalytic carbonyl addition reactions with polymer-immobilized CrF2
  作者：Michio Kurosu

  DOI：10.1016/j.tetlet.2006.03.071

  日期：2006.5

  A monomeric [Cr(pyridine)(4)F-2]Br-+(-) is immobilized onto the dipyridyl-TentaGel resin. Allylations of aldehydes with 5-10 mol % of the CrF2-dipyridyi-TentaGel resin 2/Mn/TMSCl in THF provide the corresponding homoallylic alcohols in excellent yields after TMS-desilylations with a polymer-supported ammonium fluoride 3. The recovered CrF2-dipyridyi-TentaGel resins can be utilized multiple times without a decrease of reactivity. (c) 2006 Elsevier Ltd. All rights reserved.
• Gaudemar,M.; Travers,S., Comptes Rendus des Seances de l'Academie des Sciences, Serie C: Sciences Chimiques, 1966, vol. 262, p. 139 - 141
  作者：Gaudemar,M.、Travers,S.

  DOI：——

  日期：——
• A practical procedure of low valent tin mediated Barbier allylation of aldehydes in wet solvent
  作者：Conxín Vilanova、María Sánchez-Péris、Steven Roldán、Bhaskar Dhotare、Miguel Carda、Angshuman Chattopadhyay

  DOI：10.1016/j.tetlet.2013.09.096

  日期：2013.11

  Use of aluminium as the reducing metal in spontaneous bimetal redox reaction has been elegantly exploited for allylation/crotylation of aldehydes in wet solvent. Here, low valent tin was prepared in situ by reduction of SnCl2 center dot 2H(2)O with aluminium in THF/water. The resulting low valent tin acted as an efficient mediator for allylation and crotylation of aldehydes (3a-q) producing the corresponding homoallylic alcohols. The efficacy of this procedure was due to its operational simplicity, practical viability, inexpensiveness, good yields of the products and short reaction time. (C) 2013 Elsevier Ltd. All rights reserved.