2,4-hexadienal | 20432-44-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,4-hexadienal
• 英文别名: (2E)-hexa-2,4-dienal；sorbaldehyde；trans-Hexadienal
• CAS: 20432-44-4
• 化学式: C₆H₈O
• 分子量: 96.1289
• InChiKey: BATOPAZDIZEVQF-FCEBADDRSA-N

物化性质

• 沸点：
  155.9±9.0 °C(Predicted)
• 密度：
  0.857±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  7
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2,4-hexadienal 在 bis(2,4,6-trimethylpyridine)silver(I) hexafluorophosphate 、 碘 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 2.95h， 生成 (+/-)-(2S,3R,4S,4aS,7S,7aS)-hexahydro-4-hydroxy-3-iodo-7-methyl-2-(1E)-1-propenyl-5H-furo[3,4-b]pyran-5-one
  参考文献：
  名称：

  Synthesis of (−)-TAN-2483A. Revision of the Structures and Syntheses of (±)-FD-211 (Waol A) and (±)-FD-212 (Waol B)

  摘要：

  [GRAPHICS]The structure of waol A has been revised from 1 to 6, the vinylogue of TAN-2483 A (5). Aldol reaction of 10b(c) with 2,4-hexadienal (11) affords 9b(c), which is subjected to iodoetherification with bis(sym-collidine)IPF6 to provide 8b(c). Treatment with Et3N in CH2Cl2 completes three-step syntheses of TAN-2483A (5) and waol A (6).

  DOI：

  10.1021/ol0273405
• 作为产物：
  描述：

  sorbaldehyde dimethylacetal 在 对甲苯磺酸 作用下， 以 水 、 丙酮 为溶剂， 反应 0.17h， 生成 2,4-hexadienal
  参考文献：
  名称：

  摘要：

  Using (2E)-4,4-dimethoxy-2-butenal as starting compound, methods were developed for synthesis of (2E,4E)- and (2E,4Z)-dimethoxyalkadienes. Deacetalization of the latter gives with high yield the corresponding dienals which are naturally occurring compounds and also synthons for preparation of conjugated dienes as key compounds for building up other natural products.

  DOI：

  10.1023/a:1012479213224

文献信息

• Synthesis of conjugated multiunsaturated thioesters via one-pot TiCl4-promoted aldol condensation
  作者：Alex Boateng、Tokifumi Harada、Yasuhiko Ashikari、Makoto Nakajima、Masaharu Sugiura

  DOI：10.1016/j.tetlet.2020.152280

  日期：2020.9

  TiCl4-promoted aldol condensations of S-4-chlorophenyl thioesters with enals or dienals led to the production of dienyl or trienyl thioesters in good yields. Due to good crystallinity, products with high E/Z ratios were obtained by simple filtration in many cases. Reduction of the thioester moiety by DIBAL-H afforded the corresponding unsaturated aldehydes while suppressing the E/Z-isomerization and

  TiCl 4促进的S -4-氯苯基硫酯与烯醛或二烯醛的醛醇缩合导致二烯基或三烯基硫酯的高收率生产。由于良好的结晶度，在许多情况下，通过简单的过滤即可获得具有高E / Z比的产品。用DIBAL-H还原硫酯部分可得到相应的不饱和醛，同时抑制E / Z异构化和过度还原。该方法可用于制备天然产物如鬼臼菌素和金黄色素的简单合成中间体。溴三烯基硫酯产物通过以下方式转化为四烯基硫酯 钯催化的交叉偶联而不会影响硫酯部分。
• A Simple Organocatalytic Enantioselective Cyclopropanation of α,β-Unsaturated Aldehydes
  作者：Ramon Rios、Henrik Sundén、Jan Vesely、Gui-Ling Zhao、Pawel Dziedzic、Armando Córdova

  DOI：10.1002/adsc.200700032

  日期：2007.5.7

  A highly chemo- and enantioselective organocatalytic cyclopropanation of α,β-unsaturated aldehydes with bromomalonate and 2-bromoacetoacetate esters is presented. The reaction is catalyzed by chiral amines and gives access to 2-formylcyclopropanes in high yields and up to 99 % ee.

  提出了具有溴代丙二酸酯和2-溴代乙酰乙酸酯的α，β-不饱和醛的高度化学和对映选择性的有机催化环丙烷化。该反应由手性胺催化，可以高收率和高达99％ee的产率生成2-甲酰基环丙烷。
• Dirhodium(<scp>ii</scp>)/P(<i>t</i>-Bu)₃ catalyzed tandem reaction of α,β-unsaturated aldehydes with arylboronic acids
  作者：Ziling Ma、Yuanhua Wang

  DOI：10.1039/c8ob01997e

  日期：——

  catalyst for the synthesis of aryl alkyl ketones by the tandem reaction of α,β-unsaturated aromatic or aliphatic aldehydes with arylboronic acids. This tandem procedure included arylation followed by the isomerization reaction. This method exhibits good functional group tolerance and has a broad substrate scope. With the conjugated aldehydes, the one-step synthesis of γ,δ-unsaturated ketones was realized

  提倡将膦连接的乙酸二铑（II）用作通过α，β-不饱和芳族或脂族醛与芳基硼酸的串联反应合成芳基烷基酮的催化剂。该串联过程包括芳基化，然后进行异构化反应。该方法表现出良好的官能团耐受性并且具有广泛的底物范围。通过共轭醛，通过该反应实现了γ，δ-不饱和酮的一步合成。值得注意的是，Rh-P键的长度是影响催化反应的重要因素。轴向烷基膦与芳基膦连接的二吡啶（II）晶体结构的比较分析）乙酸盐表明，与较长的Rh-P键相比，较短的Rh-P键长度有利于异构化过程。另外，反应完成后可以回收二吡啶（II）化合物。
• Enantioselective Organocatalyzed Vinylogous Michael Reactions of 3-Alkylidene Oxindoles with Enals
  作者：Junjun Feng、Xin Li、Jin-Pei Cheng

  DOI：10.1021/acs.joc.6b02582

  日期：2017.2.3

  chiral TBS-protected diphenylprolinol catalyst. The γ-substituted alkylidene oxindoles obtained bear a chiral tertiary center and are afforded in moderate to good yields and good to excellent enantioselectivities.

  使用手性TBS保护的二苯基脯氨醇催化剂已经实现了3-亚烷基氧吲哚和烯醛的有效的不对称乙烯基类迈克尔加成。所获得的γ-取代的亚烷基羟吲哚具有手性叔中心，并以中等至良好的产率和良好至优异的对映选择性提供。
• Synthesis of Vinyl Boronates from Aldehydes by a Practical Boron–Wittig Reaction
  作者：John R. Coombs、Liang Zhang、James P. Morken

  DOI：10.1021/acs.orglett.5b00480

  日期：2015.4.3

  A highly stereoselective boron-Wittig reaction between stable and readily accessible 1,1-bis(pinacolboronates) and aldehydes furnishes a variety of synthetically useful di- and trisubstituted vinyl boronate esters.

  稳定且易于获得的1,1-双（频哪醇硼酸酯）与醛之间的高度立体选择性的硼-维蒂希反应提供了各种合成上有用的二和三取代的乙烯基硼酸酯。