2-[(Z)-(2-butenyl)oxy]benzaldehyde | 28809-09-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-[(Z)-(2-butenyl)oxy]benzaldehyde
• 英文别名: 2-but-2c-enyloxy-benzaldehyde；2-[(Z)-but-2-enoxy]benzaldehyde
• CAS: 28809-09-8
• 化学式: C₁₁H₁₂O₂
• 分子量: 176.215
• InChiKey: AHJIYXHQGYKDNR-IHWYPQMZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 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-[(Z)-(2-butenyl)oxy]benzaldehyde 、 N-甲基羟胺 以 甲苯 为溶剂， 生成 1,3t-dimethyl-(3ar,9bc)-1,3a,4,9b-tetrahydro-3H-chromeno[4,3-c]isoxazole
  参考文献：
  名称：

  Ueber die stereochemie intramolekularer nitron-olefin-additionen

  摘要：

  DOI：

  10.1016/s0040-4039(01)97924-9
• 作为产物：
  描述：

  (Z)-1-氯丁-2-烯 、 邻甲基苄醇 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 24.0h， 以69%的产率得到2-[(Z)-(2-butenyl)oxy]benzaldehyde
  参考文献：
  名称：

  Microwave-assisted solvent-free intramolecular 1,3-dipolar cycloaddition reactions leading to hexahydrochromeno[4,3-b]pyrroles: scope and limitations

  摘要：

  We report the microwave-assisted solvent-free synthesis of hexahydrochromeno[4,3-b]pyrroles. Intramolecular 1,3-dipolar cycloadditions proceed under these conditions within 15-40 min in 16-84% yields. An influence of the microwave irradiation upon various [3+2] cycloaddition reaction intermediates was studied. Additionally, a scope and limitations of these reactions including an influence of the dipolarophile geometry upon the cycloaddition selectivity and steric demands of the dipole upon its reactivity were also disclosed. These observations led us to postulate a preferable transition state of the reaction. Finally, an influence of the microwave irradiation to the isomerization of activated olefins was also described. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.10.074

文献信息

• Tandem Claisen Rearrangement/6-<i>endo</i>Cyclization Approach to Allylated and Pren­ylated Chromones
  作者：Bernd Schmidt、Martin Riemer、Uwe Schilde

  DOI：10.1002/ejoc.201501151

  日期：2015.12

  o-acylphenols reacted upon microwave irradiation to form C-allylated or -prenylated chromone derivatives, depending on the substitution pattern of the arene and the allyl substituent. The reaction proceeds through a tandem Claisen rearrangement and 6-endo-trig or 6-endo-dig cyclization sequence. For prenyl ethers, the tandem sequence can be extended by a Cope rearrangement to furnish 6-prenylchromones.

  源自邻酰基苯酚的烯丙基、二甲基烯丙基和异戊二烯醚在微波辐射下反应形成 C-烯丙基化或异戊二烯化色酮衍生物，具体取决于芳烃和烯丙基取代基的取代模式。该反应通过串联克莱森重排和 6-endo-trig 或 6-endo-dig 环化序列进行。对于异戊二烯醚，串联序列可以通过 Cope 重排扩展以提供 6-异戊二烯色酮。该方法可用于合成天然产物和药物。
• Intramolecular reactivity of functionalized arylcarbenes: 2-allyloxyphenylcarbenes
  作者：Frank Gotzhein、Wolfgang Kirmse

  DOI：10.1016/s0040-4039(97)00090-7

  日期：1997.2

  2-Allyloxyphenylcarbenes (8) undergo intramolecular addition (→ 9) and (formal) CH insertion (→ 11) competitively. Stereochemical labels indicate that 11 and major amounts of 9 arise from triplet 8. The intermolecular OH insertion of singlet 8 with methanol (neat) is ca. 50 times faster than intramolecular addition. Under these conditions, intramolecular reactions and intersystem crossing of triplet

  2- Allyloxyphenylcarbenes（8）经受分子内加成（→ 9）和（正式）CH插入（→ 11）竞争性。立体化学标记表明，三重态8产生11个和9的大部分。单峰8与甲醇（纯净）的分子间OH插入大约为。比分子内添加快50倍。在这些条件下，分子内反应和三重态的系间窜越8继续进行以相似的速率（ķ Ť〜ķ TS）。