trans-1,3-dihydro-1-methoxy-3-phenylisobenzofuran | 103934-77-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异香豆素
• 英文名称: trans-1,3-dihydro-1-methoxy-3-phenylisobenzofuran
• 英文别名: (1S,3R)-1-methoxy-3-phenyl-1,3-dihydro-2-benzofuran
• CAS: 103934-77-6
• 化学式: C₁₅H₁₄O₂
• 分子量: 226.275
• InChiKey: FAYAEINVGRNNKX-CABCVRRESA-N

物化性质

• 沸点：
  345.5±42.0 °C(Predicted)
• 密度：
  1.16±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  邻苯甲酰苯甲酸 在 氢氧化钾 、 sodium tetrahydroborate 作用下， 反应 12.0h， 生成 trans-1,3-dihydro-1-methoxy-3-phenylisobenzofuran
  参考文献：
  名称：

  Stereochemistry of lithium dialkylamide-induced 1,4-eliminations leading to substituted isobenzofurans

  摘要：

  DOI：

  10.1021/jo00370a019

文献信息

• Synthesis of Oxa-Bridged Analogues of Farnesyltransferase Inhibitor RPR 115135
  作者：Céline Martin、Patrick Mailliet、Jacques Maddaluno

  DOI：10.1021/jo0100188

  日期：2001.6.1

  Two synthetic routes to new oxygen-bridged analogues of farnesyltransferase inhibitors are described that follow either a [3 + 2]/[4 + 2] or a [4 + 2]/[3 + 2] sequence of reactions. The first approach has been achieved by reacting the in situ generated phenylisobenzofuran (PIBF) 4 with pyrroline 5a and has led stereoselectively to racemic 18, which was transformed in a few steps into the target molecule 2. The second pathway relies on a key intermediate 6, obtained either by condensation of PIBF with methyl acrylate, followed by a deprotonation/selenation and an oxidation/elimination sequence, or by cycloaddition between PIBF and alpha -phenylselenoacrylate 11, followed by the same oxidation/elimination sequence. The reaction of 6 with amino dipole 7 gives diastereoselective access to pyrrolidine 25, a precursor of the second target 3, an epimer of 2.