(E)-2-(3-hydroxy-4,4-dimethyl-1-pentenyl)-2-isopropyl-1,3-dioxolane

• 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: (E)-2-(3-hydroxy-4,4-dimethyl-1-pentenyl)-2-isopropyl-1,3-dioxolane
• 英文别名: (E)-4,4-dimethyl-1-(2-propan-2-yl-1,3-dioxolan-2-yl)pent-1-en-3-ol
• 化学式: C₁₃H₂₄O₃
• 分子量: 228.332
• InChiKey: QYZJQUGAXWIVPE-VOTSOKGWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.35
• 重原子数：
  16.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  38.69
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  (E)-isopropyl 2-chlorovinyl ketone 在 三氟甲磺酸三甲基硅酯 、 4,4'-二叔丁基苯并 、 lithium 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 21.67h， 生成 (E)-2-(3-hydroxy-4,4-dimethyl-1-pentenyl)-2-isopropyl-1,3-dioxolane
  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

• 2-Substituted (E)-2-(2-lithioethenyl)-1,3-dioxolanes: New diastereoisomeric pure β-acylvinyl anion equivalents
  作者：Abderrazak Bachki、Francisco Foubelo、Miguel Yus

  DOI：10.1016/s0040-4039(00)78364-x

  日期：1994.10

  The reaction of (E)-chloroketals 1 with lithium powder and a catalytic amount of DTBB (4 mol %) in THF at -90 degrees C followed by treatment with different electrophiles [H2O, D2O, Bu(t)CHO, PhCHO, Me(2)CO,(CH2)(4)CO, PhCOMe] at -90 to -60 degrees C affords, after hydrolysis with water, the expected functionalised protected (E)-alpha,beta-unsaturated ketones 3. The deprotection of products 3 is easily achieved with silica gel/aqueous oxalic acid (cat.) to yield (E)-functionalised alkenones 5.
• 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.