3-[(2R,3R)-3-Methyl-3-(4-methyl-pent-3-enyl)-oxiranyl]-propionaldehyde | 287481-36-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-[(2R,3R)-3-Methyl-3-(4-methyl-pent-3-enyl)-oxiranyl]-propionaldehyde
• 英文别名: 3-[(2R,3R)-3-methyl-3-(4-methylpent-3-enyl)oxiran-2-yl]propanal
• CAS: 287481-36-1
• 化学式: C₁₂H₂₀O₂
• 分子量: 196.29
• InChiKey: RFUYVQIKZOOBBE-VXGBXAGGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  14
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  29.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-[(2R,3R)-3-Methyl-3-(4-methyl-pent-3-enyl)-oxiranyl]-propionaldehyde 在 chromium dichloride 、 三氟乙酸 、 nickel dichloride 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 (2R)-6-methyl-2-[(2S,5S)-5-prop-1-en-2-yloxolan-2-yl]hept-5-en-2-ol
  参考文献：
  名称：

  Tandem organochromium-coupling and epoxide ring opening: a direct approach for the synthesis of cyclic ethers

  摘要：

  A two-step protocol for the convergent formation of cyclic ethers has been demonstrated. This involves the chemoselective 1,2-addition of vinylchromium species to a 4,5-epoxy aldehyde to generate phi,delta-epoxy alcohols followed by acid-induced transetherification to generate substituted tetrahydrofuran and pyran products. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)00526-8
• 作为产物：
  描述：

  (2R,3R)-3-methyl-3-(4-methyl-3-pentenyl)oxiranemethanol 在 Rh/Al₂O₃ 四氢呋喃 、 吡啶 、 pyridine-SO3 complex 、 二异丁基氢化铝 、 二甲基亚砜 、 三乙胺 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 生成 3-[(2R,3R)-3-Methyl-3-(4-methyl-pent-3-enyl)-oxiranyl]-propionaldehyde
  参考文献：
  名称：

  Tandem organochromium-coupling and epoxide ring opening: a direct approach for the synthesis of cyclic ethers

  摘要：

  A two-step protocol for the convergent formation of cyclic ethers has been demonstrated. This involves the chemoselective 1,2-addition of vinylchromium species to a 4,5-epoxy aldehyde to generate phi,delta-epoxy alcohols followed by acid-induced transetherification to generate substituted tetrahydrofuran and pyran products. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)00526-8

文献信息

• Tandem organochromium-coupling and epoxide ring opening: a direct approach for the synthesis of cyclic ethers
  作者：Isabel C González、Craig J Forsyth

  DOI：10.1016/s0040-4039(00)00526-8

  日期：2000.5

  A two-step protocol for the convergent formation of cyclic ethers has been demonstrated. This involves the chemoselective 1,2-addition of vinylchromium species to a 4,5-epoxy aldehyde to generate phi,delta-epoxy alcohols followed by acid-induced transetherification to generate substituted tetrahydrofuran and pyran products. (C) 2000 Elsevier Science Ltd. All rights reserved.