6-(1-hydroxy-1-methylethyl)-1,4-dioxaspiro[4,5]dec-6-ene | 189870-20-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-(1-hydroxy-1-methylethyl)-1,4-dioxaspiro[4,5]dec-6-ene
• 英文别名: 2-(1,4-Dioxaspiro[4.5]dec-6-en-6-yl)propan-2-ol；2-(1,4-dioxaspiro[4.5]dec-6-en-6-yl)propan-2-ol
• CAS: 189870-20-0
• 化学式: C₁₁H₁₈O₃
• 分子量: 198.262
• InChiKey: HYVXWBMJUAVRGR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-(1-hydroxy-1-methylethyl)-1,4-dioxaspiro[4,5]dec-6-ene 在 草酸 、 silica gel 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 3.0h， 生成 2-(1-hydroxy-1-methylethyl)-2-cyclohexenone
  参考文献：
  名称：

  Ketalised α- and β-lithiated α,β-unsaturated ketones: New masked acylvinyl anion equivalents

  摘要：

  The reaction of chloroketals 1, 5 and 10 with an excess of lithium powder and a catalytic amount of DTBB (4-5%) in THF at -78 or -90 degrees C leads to the corresponding functionalised organolithium compounds 2, 6 and 11, respectively, resulting from a chlorine/lithium exchange; treatment of these intermediates with different electrophiles [H2O, D2O, Me(3)SiCl, Bu(t)CHO, PhCHO, Me(2)CO, (CH2)(4)CO, (CH2)(5)CO, PhCOMe] affords, after hydrolysis with water, the corresponding products 3, 7 and 12, respectively. Careful acidic hydrolysis of these ketalised products with a 10% aqueous solution of oxalic acid leads to the expected ketones 4, 9 and 13, respectively. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00187-7
• 作为产物：
  描述：

  2-chlorocyclohex-2-en-1-one 在 4,4'-二叔丁基苯并 、 lithium 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 苯 为溶剂， 反应 5.17h， 生成 6-(1-hydroxy-1-methylethyl)-1,4-dioxaspiro[4,5]dec-6-ene
  参考文献：
  名称：

  Ketalised α- and β-lithiated α,β-unsaturated ketones: New masked acylvinyl anion equivalents

  摘要：

  The reaction of chloroketals 1, 5 and 10 with an excess of lithium powder and a catalytic amount of DTBB (4-5%) in THF at -78 or -90 degrees C leads to the corresponding functionalised organolithium compounds 2, 6 and 11, respectively, resulting from a chlorine/lithium exchange; treatment of these intermediates with different electrophiles [H2O, D2O, Me(3)SiCl, Bu(t)CHO, PhCHO, Me(2)CO, (CH2)(4)CO, (CH2)(5)CO, PhCOMe] affords, after hydrolysis with water, the corresponding products 3, 7 and 12, respectively. Careful acidic hydrolysis of these ketalised products with a 10% aqueous solution of oxalic acid leads to the expected ketones 4, 9 and 13, respectively. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00187-7

文献信息

• Ketalised α- and β-lithiated α,β-unsaturated ketones: New masked acylvinyl anion equivalents
  作者：Abderrazak Bachki、Francisco Foubelo、Miguel Yus

  DOI：10.1016/s0040-4020(97)00187-7

  日期：1997.3

  The reaction of chloroketals 1, 5 and 10 with an excess of lithium powder and a catalytic amount of DTBB (4-5%) in THF at -78 or -90 degrees C leads to the corresponding functionalised organolithium compounds 2, 6 and 11, respectively, resulting from a chlorine/lithium exchange; treatment of these intermediates with different electrophiles [H2O, D2O, Me(3)SiCl, Bu(t)CHO, PhCHO, Me(2)CO, (CH2)(4)CO, (CH2)(5)CO, PhCOMe] affords, after hydrolysis with water, the corresponding products 3, 7 and 12, respectively. Careful acidic hydrolysis of these ketalised products with a 10% aqueous solution of oxalic acid leads to the expected ketones 4, 9 and 13, respectively. (C) 1997 Elsevier Science Ltd.