dimethyl 2,7-dimethyl-octa-4-enedioate | 100315-85-3

• 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: dimethyl 2,7-dimethyl-octa-4-enedioate
• 英文别名: 2,7-dimethyl-4-octenedioic acid dimethyl ester；2,7-dimethyl-oct-4-enedioic acid dimethyl ester；2,7-Dimethyl-oct-4-endisaeure-dimethylester；dimethyl (E)-2,7-dimethyloct-4-enedioate
• CAS: 100315-85-3
• 化学式: C₁₂H₂₀O₄
• 分子量: 228.288
• InChiKey: BVURTTHGMDWYFM-AATRIKPKSA-N

物化性质

• 沸点：
  265.3±20.0 °C(Predicted)
• 密度：
  1.001±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  16
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  dimethyl 2,7-dimethyl-octa-4-enedioate 在 lithium aluminium tetrahydride 、 正丁基锂 、 草酰氯 、 phosphorus pentoxide 、 二甲基亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 23.33h， 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 、 硫酸 作用下， 以 水 为溶剂， 反应 132.0h， 生成 dimethyl 2,7-dimethyl-octa-4-enedioate
  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

• 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。
• Buchta; Schlesinger, Justus Liebigs Annalen der Chemie, 1955, vol. 598, p. 1,22
  作者：Buchta、Schlesinger

  DOI：——

  日期：——
• 2,7-dimethyl-octa-2,4-dienedioic acid a possible by-product of abscisic acid biosynthesis in the tomato
  作者：Robert S.T. Linforth、W.Russell Bowman、David A. Griffin、Peter Hedden、Brian A. Marples、Ian B. Taylor

  DOI：10.1016/s0031-9422(00)82259-1

  日期：1987.1
• Sulfone Coupling and Double-Elimination Strategy for Carotenoid Synthesis
  作者：Samar Kumar Guha、Sangho Koo

  DOI：10.1021/jo0516335

  日期：2005.11.1

  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.