(E)-5-Morpholinopent-2-en-4-inal | 168106-71-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 恶嗪烷类
• 英文名称: (E)-5-Morpholinopent-2-en-4-inal
• 英文别名: (E)-5-morpholin-4-ylpent-2-en-4-ynal
• CAS: 168106-71-6
• 化学式: C₉H₁₁NO₂
• 分子量: 165.192
• InChiKey: BDNXDQNRTJAZIW-HNQUOIGGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-5-Morpholinopent-2-en-4-inal 在 氢氟酸 作用下， 以81%的产率得到2-morpholinopyrylium fluoride
  参考文献：
  名称：

  5-取代的5-氨基戊二烯的重排。

  摘要：

  诱导开环3→4需要强亲核试剂，因为由5-X-取代的5-氨基戊-2,4-二烯2经酸处理形成的吡喃鎓盐中间体3由于“芳族”稳定作用而几乎没有反应性。然而，这允许容易地从“推挽”烯炔1获得各种2-氨基吡啶鎓盐3。X ＝ OAc，F，Cl，Br，I，OPh。

  DOI：

  10.1002/(sici)1521-3773(19980817)37:15<2138::aid-anie2138>3.0.co;2-5
• 作为产物：
  描述：

  1,1,2-Trichloro-2-morpholinoethen 在 四(三苯基膦)钯 正丁基锂 、 四丁基溴化铵 作用下， 以 四氢呋喃 为溶剂， 反应 6.5h， 生成 (E)-5-Morpholinopent-2-en-4-inal
  参考文献：
  名称：

  合成von'Push-Pull'- Eninen †

  摘要：

  推挽式烯炔的合成

  DOI：

  10.1002/hlca.19960790118

文献信息

• S�ure-Additionen an ?Push-Pull?-Enine. Erste Beobachtung einer Umlagerung von 5-Chloro-5-(dialkylamino)pentadienalen
  作者：Daniel Berger、Markus Neuenschwander

  DOI：10.1002/hlca.19960790119

  日期：1996.2.7

  Reaction of ‘Push-Pull’ Enynes with Acids. First Observation of a Rearrangement of 5-Chloro-5-(dialkylamino)pentadienals

  “推挽式”烯炔与酸的反应。对5-氯-5-（二烷基氨基）戊二烯醛重排的首次观察
• Umlagerung von 5-Amino-5-X-pentadienalen zu 2-Aminopyrylium-Salzen
  作者：Fabian Fischer、Daniel Berger、Markus Neuenschwander

  DOI：10.1002/(sici)1522-2675(19981007)81:10<1792::aid-hlca1792>3.0.co;2-z

  日期：1998.10.7

  Various 2-aminopyrylium salts 7 (X = Cl, Br, I) are available in a simple one-pot procedure by reacting 'push-pull' enynes 5 with equivalent amounts of HCl, HBr, or HI. On the other hand, reaction of NF or AcOH with 'push-pull' enynes 5 is considerably slower so that an excess of HF or AcOH I is needed for the reaction to 7 (X = F, AcO). The 2-aminopyrylium salts 7 are the key intermediates in the postulated rearrangement of 5-amino-5-halogeno-pentadienals 6 to 5-halogenopenta-2,3-dienamides 8 (Scheme 1, bottom), which is vinylogous to the well-known rearrangement of 3-amino-3-X-propenals 2 to 3-X-propenamides 3 (Scheme I, top).
• Die Aminopentadienal-Umlagerung
  作者：Fabian Fischer、Markus Neuenschwander

  DOI：10.1002/(sici)1522-2675(19981216)81:12<2282::aid-hlca2282>3.0.co;2-m

  日期：1998.12.16

  Contrary to the rearrangement of 3-amino-3-X-propenals, which easily gives 3-X-propenamides at Io cv temperature, the postulated rearrangement (Scheme I) of the vinylogous 5-amino-5-X-pentadienals 2 normally stops at the level of (2H-pyran-2-ylidene)ammonium salts 4. The main reason is that salts of type 4 are highly delocalized low-energy. charged species which makes addition 4-5 of weak nucleophiles difficult. In this paper, the first examples of the so-called 'aminopentadienal' rearrangement art: reported. Ring-opening 4 - 6 is facilitated by nucleophilic counter ions like X = PhO (see Scheme 4) or by adding an excess of 'nucleophilic auxiliaries' such as Et3N or EtOH (see Scheme). In a quite interesting sequence of steps, 5-phenoxy-5-(pyrrol-1-yl)penta-2,4-dienal (2g; X=PhO) is easily transformed into 5H-pyrrolo[1,2-a]azepin-5-one (9) (Scheme 5).
• Synthese von ?Push-Pull?- Eninen
  作者：Daniel Berger、Andreas Bartlome、Markus Neuenschwander

  DOI：10.1002/hlca.19960790118

  日期：1996.2.7

  Synthesis of ‘Push-Pull’ Enynes

  推挽式烯炔的合成
• Rearrangement of 5-Substituted 5-Aminopentadienals
  作者：Fabian Fischer、Daniel Berger、Markus Neuenschwander

  DOI：10.1002/(sici)1521-3773(19980817)37:15<2138::aid-anie2138>3.0.co;2-5

  日期：1998.8.17

  Strong nucleophiles are needed for inducing ring opening 3→4 since the pyrylium salt intermediates 3, formed from 5-X-substituted 5-aminopenta-2,4-dienals 2 upon treatment with acid, are quite unreactive due to "aromatic" stabilization. However, this allows an easy access to a variety of 2-aminopyrylium salts 3 from "push-pull" enynes 1. X=OAc, F, Cl, Br, I, OPh.

  诱导开环3→4需要强亲核试剂，因为由5-X-取代的5-氨基戊-2,4-二烯2经酸处理形成的吡喃鎓盐中间体3由于“芳族”稳定作用而几乎没有反应性。然而，这允许容易地从“推挽”烯炔1获得各种2-氨基吡啶鎓盐3。X ＝ OAc，F，Cl，Br，I，OPh。