[2-(Dimethoxymethyl)phenyl]-phenylmethanol | 349552-84-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: [2-(Dimethoxymethyl)phenyl]-phenylmethanol
• CAS: 349552-84-7
• 化学式: C₁₆H₁₈O₃
• 分子量: 258.317
• InChiKey: LXPNZLHNGLAQCX-UHFFFAOYSA-N

物化性质

• 沸点：
  360.9±37.0 °C(Predicted)
• 密度：
  1.123±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 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：

  [2-(Dimethoxymethyl)phenyl]-phenylmethanol 在 Dowex 50W-8.50 作用下， 以 甲醇 为溶剂， 反应 20.0h， 生成 cis-1,3-dihydro-1-methoxy-3-phenylisobenzofuran 、 trans-1,3-dihydro-1-methoxy-3-phenylisobenzofuran
  参考文献：
  名称：

  Synthesis of Oxa-Bridged Analogues of Farnesyltransferase Inhibitor RPR 115135

  摘要：

  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.

  DOI：

  10.1021/jo0100188
• 作为产物：
  描述：

  邻溴苯甲醛 在 正丁基锂 、 Dowex 50W-8.50 作用下， 以 甲醇 、 乙醚 为溶剂， 反应 24.5h， 生成 [2-(Dimethoxymethyl)phenyl]-phenylmethanol
  参考文献：
  名称：

  Synthesis of Oxa-Bridged Analogues of Farnesyltransferase Inhibitor RPR 115135

  摘要：

  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.

  DOI：

  10.1021/jo0100188

文献信息

• Regioselectivity in arene-catalyzed reductive lithiation of acetals of chlorobenzaldehydes
  作者：Ugo Azzena、Giovanna Dettori、Giuseppe Sforazzini、Miguel Yus、Francisco Foubelo

  DOI：10.1016/j.tet.2005.11.006

  日期：2006.2

  The regioselectivity of arene-catalyzed reductive lithiation of acetals of chlorobenzaldehydes strongly depends on the form of lithium metal employed as a reducing agent. According to previous findings, naphthalene catalyzed reductions run in the presence of lithium powder (high Na content) led to competitive metalations of both aromatic carbon–chlorine and benzylic carbon–oxygen bonds. At variance

  芳烃催化的氯苯甲醛缩醛缩醛锂化的区域选择性在很大程度上取决于用作还原剂的锂金属的形式。根据以前的发现，在锂粉（高Na含量）的存在下，萘催化的还原反应导致芳族碳-氯键和苄基碳-氧键的竞争性金属化。与这些结果不同的是，在锂线（高或低Na含量）的存在下，萘催化的还原反应会导致芳族碳-氯键的高度区域选择性金属化。这些结果揭示了选择性应用芳烃催化的还原锂化反应的新可能性。
• 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.