(E)-5-Phenoxypent-2-en-4-inal | 270918-57-5

• 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: (E)-5-Phenoxypent-2-en-4-inal
• 英文别名: 5-phenoxypent-2-en-4-ynal；(E)-5-phenoxypent-2-en-4-ynal
• CAS: 270918-57-5
• 化学式: C₁₁H₈O₂
• 分子量: 172.183
• InChiKey: FPOYJPLTPYCNLM-GORDUTHDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 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：

  (E)-5-Phenoxypent-2-en-4-inal 在 盐酸 作用下， 以 四氢呋喃 、 氘代氯仿 为溶剂， 反应 241.0h， 生成 phenyl (2E,4E)-5-chloropenta-2,4-diene-1-carboxylate
  参考文献：
  名称：

  摘要：

  Contrary to the rearrangement of 3-amino-3-X-prop-2-enals 2 (R = H),which easily give 3-X-prop-2-enamides 3 at low temperature, the postulated rearrangement (Scheme 1) of the vinylogous 5-amino-5-X-penta-2,4-dienals 6(R = H)normally stops at the level of 2-aminopyrylium salts 7. The main reason is that the charge in salts of type 7 is highly delocalized, leading to low-energy species, which make addition of weak nucleophiles difficult. In this paper, two concepts for increasing the chances of the 'aminopentadienal rearrangement' 6 --> -->, 8 are presented and substantiated by typical experiments. On one side, the easily available 2-aminopyrylium chlorides 7 (X = Cl) are reacted with a twofold excess of secondary amines (Scheme 2) to give 5-(dialkylamino)penta-2,4-dienamides of type 9 and 10. On the other hand, after replacing the amino groups of 6 by PhO and EtO groups the corresponding 5-chloro-5-phenoxy-(13b) and 5-chloro-5-ethoxypenta-2,4-dienals (13a) easily rearrange at low temperature to give 5-chlorapenta-2,4-diene-1-carboxylates 18a and 18b, respectively, which are now obviously lower in energy than the corresponding pyrylium-salt intermediates 16 (Scheme 4).

  DOI：

  10.1002/1522-2675(20000607)83:6<1182::aid-hlca1182>3.0.co;2-t
• 作为产物：
  描述：

  (E)-3-Iodoprop-2-enal 、 1-Phenoxy-2-(trimethylstannyl)ethyn 在 四(三苯基膦)钯 Et₄(+)Cl(-) 作用下， 以 四氢呋喃 为溶剂， 反应 1.08h， 以69%的产率得到(E)-5-Phenoxypent-2-en-4-inal
  参考文献：
  名称：

  摘要：

  含有乙氧基（EtO）、苯氧基（PhO）、苯硫基（PhS）和甲硫基（MeS）作为π供体的"推-拉"型炔烯化合物14a-d，通过催化条件下将炔亚胺锡化物10与3-碘丙-2-烯醛（Scheme 4）进行偶联反应而合成。

  DOI：

  10.1002/(sici)1522-2675(20000315)83:3<641::aid-hlca641>3.0.co;2-u

文献信息

• ——
  作者：Christian Bacilieri、Markus Neuenschwander

  DOI：10.1002/(sici)1522-2675(20000315)83:3<641::aid-hlca641>3.0.co;2-u

  日期：2000.3.15

  'Push-pull' enynes 14a-d with EtO, PhO, PhS, and MeS groups as pi-donors have been synthesized by catalyzed coupling of stannyl ynamines 10 with 3-iodoprop-2-enal (Scheme 4).

  含有乙氧基（EtO）、苯氧基（PhO）、苯硫基（PhS）和甲硫基（MeS）作为π供体的"推-拉"型炔烯化合物14a-d，通过催化条件下将炔亚胺锡化物10与3-碘丙-2-烯醛（Scheme 4）进行偶联反应而合成。
• ——
  作者：Christian Bacilieri、Stefanie Reic、Markus Neuenschwander

  DOI：10.1002/1522-2675(20000607)83:6<1182::aid-hlca1182>3.0.co;2-t

  日期：2000.6.7

  Contrary to the rearrangement of 3-amino-3-X-prop-2-enals 2 (R = H),which easily give 3-X-prop-2-enamides 3 at low temperature, the postulated rearrangement (Scheme 1) of the vinylogous 5-amino-5-X-penta-2,4-dienals 6(R = H)normally stops at the level of 2-aminopyrylium salts 7. The main reason is that the charge in salts of type 7 is highly delocalized, leading to low-energy species, which make addition of weak nucleophiles difficult. In this paper, two concepts for increasing the chances of the 'aminopentadienal rearrangement' 6 --> -->, 8 are presented and substantiated by typical experiments. On one side, the easily available 2-aminopyrylium chlorides 7 (X = Cl) are reacted with a twofold excess of secondary amines (Scheme 2) to give 5-(dialkylamino)penta-2,4-dienamides of type 9 and 10. On the other hand, after replacing the amino groups of 6 by PhO and EtO groups the corresponding 5-chloro-5-phenoxy-(13b) and 5-chloro-5-ethoxypenta-2,4-dienals (13a) easily rearrange at low temperature to give 5-chlorapenta-2,4-diene-1-carboxylates 18a and 18b, respectively, which are now obviously lower in energy than the corresponding pyrylium-salt intermediates 16 (Scheme 4).