methyl (2Z,4E)-6-oxohexa-2,4-dienolate | 142334-76-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: methyl (2Z,4E)-6-oxohexa-2,4-dienolate
• 英文别名: Methyl 6-Oxo-2,4-cis,trans-hexadienoate；methyl (2Z,4E)-6-oxohexa-2,4-dienoate
• CAS: 142334-76-7
• 化学式: C₇H₈O₃
• 分子量: 140.139
• InChiKey: OKCKDXOUJKZELN-HZDAAVBUSA-N

物化性质

• 沸点：
  237.2±23.0 °C(Predicted)
• 密度：
  1.060±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  10
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-[(4S)-4-propan-2-yl-2-sulfanylidene-1,3-thiazolidin-3-yl]ethenolate;tin(2+);trifluoromethanesulfonate 、 methyl (2Z,4E)-6-oxohexa-2,4-dienolate 以 二氯甲烷 为溶剂， 反应 0.33h， 以60%的产率得到(2Z,4E)-(R)-6-Hydroxy-8-((S)-4-isopropyl-2-thioxo-thiazolidin-3-yl)-8-oxo-octa-2,4-dienoic acid methyl ester
  参考文献：
  名称：

  Asymmetric acetate aldol reactions in connection with an enantioselective total synthesis of macrolactin A

  摘要：

  Asymmetric aldol-like reactions of cinnamaldehyde, dienal 3 (fragment C7-C12 of macrolactin A), and dienal 4 (fragment C15-C24) with (i) chiral acetylthiazolidinethione-derived enolates, (ii) chiral boron enolates, and (iii) silyl enolates in the presence of chiral titanium-2,2'-dinaphthol complexes are compared. Use of the thiazolidinethione auxiliary and TiCl4 shows practical advantages; e.g., C5-C12 fragment 7 has been isolated enantiomerically pure in 74% yield. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/s0040-4039(96)02055-2
• 作为产物：
  描述：

  (Z)-3-碘丙烯酸甲酯 、 丙烯醛 在 palladium diacetate silver carbonate 作用下， 反应 24.0h， 生成 methyl (2Z,4E)-6-oxohexa-2,4-dienolate
  参考文献：
  名称：

  从丙酸衍生物方便地立体选择性合成共轭（2Z）-EN-4-炔酸和（2Z，4Z）-和（2Z，4E）-二烯酸衍生物

  摘要：

  钯催化的丙酸衍生物与卤化锂的一锅顺序反应，然后与末端炔烃或烯烃进行单锅顺序反应，得到共轭的（2Z）-en-4-炔酸和（2Z，4Z）-和（2Z，4E）-具有高立体选择性的二烯酸衍生物。

  DOI：

  10.1016/s0040-4039(00)92235-4

文献信息

• A convenient stereoselective synthesis of conjugated (2Z)-EN-4-ynoic and (2Z,4Z)- and (2Z,4E)-dienoic acid derivatives from propiolic acid derivatives
  作者：Xiyan Lu、Xiaoling Huang、Shengming Ma

  DOI：10.1016/s0040-4039(00)92235-4

  日期：1992.4

  The palladium-catalyzed one-pot sequential reaction of propiolic acid derivatives with lithium halides first, and then with terminal alkynes or alkenes affords conjugated (2Z) -en-4-ynoic and (2Z,4Z)- and (2Z,4E)- dienoic acid derivatives with high stereoselectivity.

  钯催化的丙酸衍生物与卤化锂的一锅顺序反应，然后与末端炔烃或烯烃进行单锅顺序反应，得到共轭的（2Z）-en-4-炔酸和（2Z，4Z）-和（2Z，4E）-具有高立体选择性的二烯酸衍生物。
• Chloroperoxidase-catalyzed oxidation of conjugated dienoic esters
  作者：Despina J Bougioukou、Ioulia Smonou

  DOI：10.1016/s0040-4039(01)02127-x

  日期：2002.1

  The chloroperoxidase (CPO)-catalyzed oxidations of dienes conjugated to an ester group were studied using tert-butyl hydroperoxide as the terminal oxidant. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Asymmetric acetate aldol reactions in connection with an enantioselective total synthesis of macrolactin A
  作者：Ángel González、Josep Aiguadé、Félix Urpí、Jaume Vilarrasa

  DOI：10.1016/s0040-4039(96)02055-2

  日期：1996.12

  Asymmetric aldol-like reactions of cinnamaldehyde, dienal 3 (fragment C7-C12 of macrolactin A), and dienal 4 (fragment C15-C24) with (i) chiral acetylthiazolidinethione-derived enolates, (ii) chiral boron enolates, and (iii) silyl enolates in the presence of chiral titanium-2,2'-dinaphthol complexes are compared. Use of the thiazolidinethione auxiliary and TiCl4 shows practical advantages; e.g., C5-C12 fragment 7 has been isolated enantiomerically pure in 74% yield. Copyright (C) 1996 Elsevier Science Ltd