5-phenylsulfonyl-1-phenylthio-3,7,11-trimethyl-2,6,10-dodecatriene | 359010-60-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 5-phenylsulfonyl-1-phenylthio-3,7,11-trimethyl-2,6,10-dodecatriene
• 英文别名: [(2E,6E)-5-(benzenesulfonyl)-3,7,11-trimethyldodeca-2,6,10-trienyl]sulfanylbenzene
• CAS: 359010-60-9
• 化学式: C₂₇H₃₄O₂S₂
• 分子量: 454.698
• InChiKey: LZSSOABGNMMCEQ-JRZXAFIKSA-N

物化性质

• 沸点：
  611.4±55.0 °C(Predicted)
• 密度：
  1.11±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.2
• 重原子数：
  31
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  67.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-phenylsulfonyl-1-phenylthio-3,7,11-trimethyl-2,6,10-dodecatriene 在 氢氧化钾 、 正丁基锂 、 LiNbMoO₆ 、 双氧水 、 sodium ethanolate 作用下， 以 四氢呋喃 、 甲醇 、 四氯化碳 、 乙醇 、 叔丁醇 为溶剂， 生成 番茄红素
  参考文献：
  名称：

  A Highly Efficient Chain-Extension Process in the Systematic Syntheses of Carotenoid Natural Products This work was supported by the RRC program of MOST and KOSEF.

  摘要：

  DOI：

  10.1002/1521-3773(20011001)40:19<3627::aid-anie3627>3.0.co;2-e
• 作为产物：
  描述：

  苯硫酚 在 copper(l) iodide 、 正丁基锂 、 三溴化磷 作用下， 以 四氢呋喃 、 乙醚 、 N,N-二甲基甲酰胺 为溶剂， 生成 5-phenylsulfonyl-1-phenylthio-3,7,11-trimethyl-2,6,10-dodecatriene
  参考文献：
  名称：

  A Highly Efficient Chain-Extension Process in the Systematic Syntheses of Carotenoid Natural Products This work was supported by the RRC program of MOST and KOSEF.

  摘要：

  DOI：

  10.1002/1521-3773(20011001)40:19<3627::aid-anie3627>3.0.co;2-e

文献信息

• Process for preparing carotenoid polyene chain compounds and intermediates for preparing the same
  申请人：——

  公开号：US20030100785A1

  公开（公告）日：2003-05-29

  The present invention provides an intermediate compound used for synthesis of polyene chain structure, that is an important moiety of carotenoid compounds, a process for preparing the same, and carotenoid polyene chain compounds prepared by using the intermediate, and, in particular, a process for preparing lycopene. The process for preparing the carotenoid polyene chain compound employs an allylic sulfone compound as starting material, which is reacted with C-5 sulfide compound to extend the carbon chain. The resultant thio-sulfone compound is oxidized, and the obtained disulfone compound is combined with C-10 di(haloallylic) sulfide compound to form a chain compound containing the desired number of carbon atoms. Then, the diallylic sulfone obtained by oxidation of the diallylic sulfide is subjected to Ramberg-Baklund reaction in order to form the central triene bond. After removal of sulfonyl groups, carotenoid polyene chain compound is obtained.

  本发明提供了一种用于合成聚烯烃链结构的中间化合物，这是类胡萝卜素化合物中的重要部分，以及制备该中间化合物的方法，以及使用该中间体制备的类胡萝卜素聚烯烃链化合物，特别是制备番茄红素的方法。制备类胡萝卜素聚烯烃链化合物的方法采用烯丙基磺酮化合物作为起始原料，与C-5硫化合物反应以延伸碳链。产生的硫代磺酮化合物被氧化，获得的二磺酮化合物与C-10二(卤代烯丙基)磺酮化合物结合，形成含有所需碳原子数量的链化合物。然后，通过氧化二烯丙基硫醚得到的二烯丙基磺酮经过Ramberg-Baklund反应，形成中央三烯键。去除磺酰基后，得到类胡萝卜素聚烯烃链化合物。
• General Preparation and Controlled Cyclization of Acyclic Terpenoids
  作者：Jinchul Kuk、Beom Soo Kim、Heejung Jung、Seyoung Choi、Jung-Youl Park、Sangho Koo

  DOI：10.1021/jo702303a

  日期：2008.3.1

  [GRAPHICS]A general preparation method of the all-(E)-polyprenols 12 has been developed from readily available geranyl sulfone by the chain-extension process utilizing the C-5 unit 5 and the chain-temination process utilizing the C5 unit 10 together with the chemoselective reductive desulfortylation. The polyprenols 12 were converted to compounds 3 containing two consecutive prenyl sulfone moieties at the tail end, which underwent the controlled electrophilic cyclization only at the carbon-carbon double bonds that were remote from the flat and rigid benzenesulfonyl groups.
• A PROCESS FOR PREPARING CAROTENOID POLYENE CHAIN COMPOUNDS AND INTERMEDIATES FOR PREPARING THE SAME
  申请人：Koo, Sangho

  公开号：EP1283826B1

  公开（公告）日：2008-03-26
• EP1283826A4
  申请人：——

  公开号：EP1283826A4

  公开（公告）日：2005-11-23
• US6747166B2
  申请人：——

  公开号：US6747166B2

  公开（公告）日：2004-06-08