2,7-dimethyl-4-octenedial | 870517-46-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,7-dimethyl-4-octenedial
• 英文别名: (E)-2,7-dimethyloct-4-enedial
• CAS: 870517-46-7
• 化学式: C₁₀H₁₆O₂
• 分子量: 168.236
• InChiKey: IFQHFALXJQLJIY-ONEGZZNKSA-N

物化性质

• 沸点：
  254.1±28.0 °C(Predicted)
• 密度：
  0.921±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  12
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,7-dimethyl-4-octenedial 在 正丁基锂 、 phosphorus pentoxide 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 21.83h， 生成 [(6E,8E,10E,16E,22E,24E,26E)-21-(benzenesulfonyl)-13,20-bis(methoxymethoxy)-2,6,10,14,19,23,27,31-octamethyldotriaconta-2,6,8,10,16,22,24,26,30-nonaen-12-yl]sulfonylbenzene
  参考文献：
  名称：

  Sulfone Coupling and Double-Elimination Strategy for Carotenoid Synthesis

  摘要：

  A highly efficient synthetic method of carotenoid compounds has been developed on the basis of the sulfone coupling and double-elimination strategy. This method highlighted the sulfone-mediated coupling with the novel C-10 dialdehyde, 2,7-dimethyl-4-octenedial, which was easily prepared and efficiently utilized in the synthesis of the conjugated polyene chains.

  DOI：

  10.1021/jo0516335
• 作为产物：
  描述：

  2,2,4,4-tetrakis(ethoxycarbonyl)-(E)-4-octene 在 氢氧化钾 、 lithium aluminium tetrahydride 、 草酰氯 、 硫酸 、 二甲基亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 133.5h， 生成 2,7-dimethyl-4-octenedial
  参考文献：
  名称：

  Sulfone Coupling and Double-Elimination Strategy for Carotenoid Synthesis

  摘要：

  A highly efficient synthetic method of carotenoid compounds has been developed on the basis of the sulfone coupling and double-elimination strategy. This method highlighted the sulfone-mediated coupling with the novel C-10 dialdehyde, 2,7-dimethyl-4-octenedial, which was easily prepared and efficiently utilized in the synthesis of the conjugated polyene chains.

  DOI：

  10.1021/jo0516335

文献信息

• Dialdehyde compound, preparation method thereof, and synthetic method of carotenoids using the same
  申请人：Koo Sang Ho

  公开号：US20090318732A1

  公开（公告）日：2009-12-24

  The novel C dialdehyde compound which can be efficiently utilized in the synthesis of carotenoid compounds based on the sulfone chemistry, the preparation method of the same, and the expeditious and practical synthetic processes for lycopene and β-carotene by the use of the above novel compound are disclosed. The syntheses of lycopene and β-carotene are characterized by the processes of the coupling reaction between two equivalents of geranyl sulfone or cyclic geranyl sulfone and the above C dialdehyde, the functional group transformation reactions of the diol in the resulting C 40 coupling products to X's (either halogens or ethers), and the double elimination reactions of the functional groups of the benzenesulfonyl and X to produce the fully conjugated polyene chain of the carotenoids.

  揭示了一种可以在基于磺酮化学的类胡萝卜素化合物合成中高效利用的C二醛化合物，以及该化合物的制备方法，以及通过使用上述新颖化合物快速实用地合成番茄红素和β-胡萝卜素的合成过程。番茄红素和β-胡萝卜素的合成特点在于通过两等量的戊二烯基磺酮或环戊二烯基磺酮与上述C二醛之间的偶联反应过程，将结果产生的C40偶联产物中的二醇的官能团转化反应为X（可能是卤素或醚），以及苯甲磺酰基和X的官能团的双消除反应，以产生类胡萝卜素的完全共轭聚烯链。
• [EN] ClO DIALDEHYDE, SYNTHETIC METHOD THEREOF, AND SYNTHETIC METHOD OF BETA-CAROTENE USING THE SAME<br/>[FR] DIALDEHYDE C10, PROCEDE DE SYNTHESE ASSOCIE, ET PROCEDE DE SYNTHESE DE BETA-CAROTENE ASSOCIE
  申请人：KOO SANGHO

  公开号：WO2006038764A1

  公开（公告）日：2006-04-13

  The novel intermediate compound which can be efficiently utilized in the synthesis of carotenoid compounds based on the sulfone chemistry, the preparation method of the same, and the practical synthetic process for preparing β-carotene by the use of the above novel compound are disclosed. The synthesis of β-carotene is characterized by the double elimination reactions of the C40 compound containing both the benzenesulfonyl group and the group X (either halogen or ether), which can be prepared by the coupling reaction of the novel C10 dialdehyde with two equivalents of the C15 allylic sulfone, followed by the functional group transformation of the resulting C40 diol either to the corresponding halide or to the ether, to produce the fully conjugated polyene chain.

  揭示了一种新型中间化合物，可在基于磺酮化学的合成中高效利用，以及该化合物的制备方法和利用上述新型化合物制备β-胡萝卜素的实际合成过程。β-胡萝卜素的合成特点是通过含有苯磺酰基和X基团（卤素或醚）的C40化合物的双消除反应来实现，该C40化合物可通过新型C10二醛与两当量的C15烯基磺酮的偶联反应制备，随后通过将得到的C40二醇的官能团转化为相应的卤化物或醚，从而产生完全共轭的聚烯烃链。
• C10 Dialdehyde, Synthetic Method Thereof, and Synthetic Method of Beta-Carotene Using the Same
  申请人：Koo Sangho

  公开号：US20080262271A1

  公开（公告）日：2008-10-23

  The novel intermediate compound which can be efficiently utilized in the synthesis of carotenoid compounds based on the sulfone chemistry, the preparation method of the same, and the practical synthetic process for preparing β-carotene by the use of the above novel compound are disclosed. The synthesis of β-carotene is characterized by the double elimination reactions of the C 40 compound containing both the benzenesulfonyl group and the group X (either halogen or ether), which can be prepared by the coupling reaction of the novel C 10 dialdehyde with two equivalents of the C 15 allylic sulfone, followed by the functional group transformation of the resulting C 40 diol either to the corresponding halide or to the ether, to produce the fully conjugated polyene chain.

  公开了一种新型中间化合物，可在基于磺酮化学的类胡萝卜素化合物合成中高效利用，以及其制备方法和利用上述新型化合物制备β-胡萝卜素的实际合成过程。β-胡萝卜素的合成特点是含有苯磺酰基和X基团（卤素或醚）的C40化合物的双消除反应，可以通过将新型C10二醛与两当量的C15烯丙基磺酮进行偶联反应来制备，然后通过将得到的C40二醇的官能团转化为相应的卤化物或醚，从而产生完全共轭的聚烯烃链。
• DIALDEHYDE COMPOUND, PREPARATION METHOD THEREOF, AND SYNTHETIC METHOD OF CAROTENOIDS USING THE SAME
  申请人：Koo Sang Ho

  公开号：US20110166391A1

  公开（公告）日：2011-07-07

  The novel C dialdehyde compound which can be efficiently utilized in the synthesis of carotenoid compounds based on the sulfone chemistry, the preparation method of the same, and the expeditious and practical synthetic processes for lycopene and β-carotene by the use of the above novel compound are disclosed. The syntheses of lycopene and β-carotene are characterized by the processes of the coupling reaction between two equivalents of geranyl sulfone or cyclic geranyl sulfone and the above C dialdehyde, the functional group transformation reactions of the diol in the resulting C 40 coupling products to X's (either halogens or ethers), and the double elimination reactions of the functional groups of the benzenesulfonyl and X to produce the fully conjugated polyene chain of the carotenoids.

  本发明公开了一种新型的C二醛化合物，可有效用于基于磺酰化学的类胡萝卜素化合物的合成，以及其制备方法和利用上述新型化合物进行番茄红素和β-胡萝卜素的迅速实用合成过程。番茄红素和β-胡萝卜素的合成特征在于，通过两当量的烯丙基磺酰化合物或环烯丙基磺酰化合物与上述C二醛之间的偶联反应，将所得的C40偶联产物中的二醇进行官能团转化反应形成X（卤素或醚），并通过苯磺酰基和X的官能团的双消除反应形成完全共轭的类胡萝卜素多烯链。
• DIADEHYDE COMPOUND, PREPARATION METHOD THEREOF, AND SYNTHETIC METHOD OF CAROTENOIDS USING THE SAME
  申请人：Koo Sang Ho

  公开号：US20110166400A1

  公开（公告）日：2011-07-07

  The novel C dialdehyde compound which can be efficiently utilized in the synthesis of carotenoid compounds based on the sulfone chemistry, the preparation method of the same, and the expeditious and practical synthetic processes for lycopene and β-carotene by the use of the above novel compound are disclosed. The syntheses of lycopene and β-carotene are characterized by the processes of the coupling reaction between two equivalents of geranyl sulfone or cyclic geranyl sulfone and the above C dialdehyde, the functional group transformation reactions of the diol in the resulting C 40 coupling products to X's (either halogens or ethers), and the double elimination reactions of the functional groups of the benzenesulfonyl and X to produce the fully conjugated polyene chain of the carotenoids.

  本发明揭示了一种可以高效地用于基于磺酰化学的类胡萝卜素化合物合成的C二醛化合物，以及其制备方法和利用上述新型化合物快速而实用地合成番茄红素和β-胡萝卜素的合成过程。番茄红素和β-胡萝卜素的合成特征在于将两当量的香叶基磺酸酯或环状香叶基磺酸酯与上述C二醛进行偶联反应，将得到的C40偶联产物中的二醇进行官能团转化反应，转化为X（卤素或醚）的官能团，然后通过苯磺酰和X的官能团的双消除反应来产生完全共轭的类胡萝卜素多烯链。