2-<2-(Benzyloxy)ethyl>benzaldehyde | 119367-94-1

• 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-<2-(Benzyloxy)ethyl>benzaldehyde
• 英文别名: 2-(2-benzyloxyethyl)benzaldehyde；2-(2-Phenylmethoxyethyl)benzaldehyde
• CAS: 119367-94-1
• 化学式: C₁₆H₁₆O₂
• 分子量: 240.302
• InChiKey: NFXYSHPWFHQDDS-UHFFFAOYSA-N

物化性质

• 沸点：
  359.6±22.0 °C(Predicted)
• 密度：
  1.104±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-<2-(Benzyloxy)ethyl>benzaldehyde 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 26.0h， 生成 7-<(Benzyloxy)methyl>bicyclo<4.2.0>octa-1,3,5-triene
  参考文献：
  名称：

  Intramolecular generation of oxonium ylides from functionalized arylcarbenes

  摘要：

  DOI：

  10.1021/ja00186a048
• 作为产物：
  描述：

  2-<2-(Benzyloxy)ethyl>benzoic acid 在 lithium aluminium tetrahydride 、 pyridinium chlorochromate 作用下， 以 乙醚 为溶剂， 反应 1.0h， 生成 2-<2-(Benzyloxy)ethyl>benzaldehyde
  参考文献：
  名称：

  Intramolecular generation of oxonium ylides from functionalized arylcarbenes

  摘要：

  DOI：

  10.1021/ja00186a048

文献信息

• The organocatalytic enantioselective [3+2] cycloaddition reaction of α,β-unsaturated aldehydes with azomethine ylides applied to the asymmetric synthesis of densely substituted pyrroloisoquinolines
  作者：Ainara Iza、Iratxe Ugarriza、Uxue Uria、Efraím Reyes、Luisa Carrillo、Jose L. Vicario

  DOI：10.1016/j.tet.2013.08.012

  日期：2013.10

  The synthesis of densely functionalized pyrrolo[2,1-a]isoquinolines was accomplished using the organocatalytic [3+2] cycloaddition between enals and azomethine ylides under iminium catalysis developed in our group some years ago as the key step. The cycloaddition proceeds smoothly yielding the corresponding pyrrolidine as a single endo diastereoisomer with enantiopurity in the range of 94–96% and further

  密集地官能化吡咯的合成[2,1-一个]异喹啉，使用下我们组开发了一些年前，作为关键步骤亚胺催化enals和甲亚胺叶立德之间的有机催化的[3 + 2]环加成来完成。环加成顺顺利得到相应的吡咯烷作为一个单一的内使用高产反应协议和最终甲磺酰化，在94-96％的范围内，将得到的cycloadducts进一步操作对映体非对映体/分子内N-烷基化序列允许目标的合成在其中在第一步骤中安装的所有立构中心的完整性得以维持的化合物。
• Stereoselective Synthesis of Chiral IBR2 Analogues
  作者：Xiao-Long Qiu、Jiewen Zhu、Guikai Wu、Wen-Hwa Lee、A. Richard Chamberlin

  DOI：10.1021/jo802607f

  日期：2009.3.6

  Two stereoselective routes were developed to synthesize optically pure IBR2 analogues 1-16. The first features addition of N-Boc-3-bromoindole 26 to the sulfinamide 25, providing a 1: 1 ratio of the separable diasteroisomers 27 and 28 in good yield. In a straightforward fashion, the sulfinamides 27 and 28 were conveniently converted into the key amines 39 and 47 over 8 steps, respectively, from which a series of 3,4-dihydroisoquinolinyl IBR2 analogues 1-14 containing fluorinated and trifluoromethylated benzyl groups were prepared. Another route highlights the highly enantioselective addition of indole to the sulfonyl amide 50 with bifunctional aminothioureas 57 and 58 as catalysts. After the reaction conditions were optimized, the desired sulfonyl amides (R)-55 and (S)-55 were obtained in 99% ee and 98% ee, respectively. Acylation of (R)-55 and (S)-55 separately and subsequent allylation gave compounds 60 and 63, respectively, which were further subjected to RCM to furnish compounds 61 and 64 and, after removal of the Boc groups, the desired IBR2 analogues 15 and 16.