(4E, 8E)-5,9,13-trimethyl-4,8,12-tetradecatrienal | 67858-78-0

• 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: (4E, 8E)-5,9,13-trimethyl-4,8,12-tetradecatrienal
• 英文别名: (4E,8E)-5,9,13-trimethyltetradeca-4,8,12-trienal；4,8,12-Tetradecatrienal, 5,9,13-trimethyl-
• CAS: 67858-78-0
• 化学式: C₁₇H₂₈O
• 分子量: 248.409
• InChiKey: IDHMAJKSCCNULC-QKXOVSGLSA-N

物化性质

• 沸点：
  350.2±21.0 °C(Predicted)
• 密度：
  0.866±0.06 g/cm3(Predicted)
• 保留指数：
  1933

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  18
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.59
• 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：

  (4E, 8E)-5,9,13-trimethyl-4,8,12-tetradecatrienal 在 四溴化碳 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 反应 2.25h， 生成 ((6E,10E)-3-Bromo-7,11,15-trimethyl-hexadeca-6,10,14-trien-1-ynyl)-trimethyl-silane
  参考文献：
  名称：

  A biomimetic synthesis of (.+-.)-petiodial. A novel palladium-catalyzed enallene cyclization

  摘要：

  DOI：

  10.1021/ja00223a075
• 作为产物：
  描述：

  角鲨烯 在 过碘酸 、 间氯过氧苯甲酸 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 生成 (4E, 8E)-5,9,13-trimethyl-4,8,12-tetradecatrienal
  参考文献：
  名称：

  Importance of the Methyl Group at C(10) of Squalene for Hopene Biosynthesis and Novel Carbocyclic Skeletons with 6/5 + 5/5 + (6) Ring System(s)

  摘要：

  [GRAPHICS]Incubation of (6E,10E,14E,18E)-2,6,10,19,23-pentamethyl-tetracosa-2,6,10,14,18,22-hexaene with Alicyclobacillus acidocaidarius hopene cyclase afforded four products having two types of carbocyclic skeletons, i.e., two hopane products and two products having an unprecedented carbocyclic skeleton of 6/5 + 5/5 +6 pentacyclic and 6/5 + 5/5 tetracyclic ring systems. The former two hopane skeletons were formed from the bioconversion of C(15)-desmethylsqualene and the latter two skeletons from that of C(10)-desmethylsqualene.

  DOI：

  10.1021/ol026180u

文献信息

• ISOPRENE OLIGOMER, POLYISOPRENE, PROCESSES FOR PRODUCING THESE MATERIALS, RUBBER COMPOSITION, AND PNEUMATIC TIRE
  申请人：Miyagi Yukino

  公开号：US20140171675A1

  公开（公告）日：2014-06-19

  The invention relates to an isoprene oligomer that contains a trans structural moiety and a cis structural moiety, which can be represented by the following formula (1), wherein at least 1 atom or group in the trans structural moiety is replaced by another atom or group. The invention also relates to a polyisoprene, which is biosynthesized using the isoprene oligomer and isopentenyl diphosphate. Further, this invention provides a rubber composition comprising the isoprene oligomer and/or the polyisoprene, and a pneumatic tire, including tire components (e.g., treads and sidewalls) formed from the rubber composition. wherein n represents an integer from 1 to 10; m represents an integer from 1 to 30; and Y represents a hydroxy group, a formyl group, a carboxy group, an ester group, a carbonyl group, or a group represented by the following formula (2):

  该发明涉及一种含有反式结构基团和顺式结构基团的异戊二烯寡聚物，可以用以下公式（1）表示，其中反式结构基团中至少有1个原子或基团被另一个原子或基团取代。该发明还涉及一种聚异戊二烯，它是使用异戊二烯寡聚物和异戊二烯二磷酸盐生物合成的。此外，该发明提供了一种橡胶组合物，包括异戊二烯寡聚物和/或聚异戊二烯，以及一种充气轮胎，其中轮胎组件（例如胎面和侧壁）由该橡胶组合物形成。 其中n表示1到10之间的整数；m表示1到30之间的整数；Y表示一个羟基、一个甲酰基、一个羧基、一个酯基、一个酰基或由以下公式（2）表示的基团。
• Synthesis of vinyl sulfide analogs of 2,3-oxidosqualene and their inhibition of 2,3-oxidosqualene lanosterol-cyclases
  作者：Yi Feng Zheng、Dharmpal S. Dodd、Allan C. Oehlschlager、Peter G. Hartman

  DOI：10.1016/0040-4020(95)00213-r

  日期：1995.5

  aldehydes. Mixtures of syn and anti α-hydroxydiphenylphosphine adducts were separated by chromatography and the syn isomers were transformed to the E-vinyl sulfides. Both (6E)-5- and (18E)-20-thia-2,3-OS inhibited OSC from Candida albicans (IC50 = 47 and 0.2 μM, respectively) and rat liver (IC50 = 7.7 and 0.32 μM, respectively). Their activities were compared with those of previously synthesized (6E)-8-

  所有反式（6 E）-5-，（10 E）-9- ，（14 E）-16-和（18 E）-20-thia-2,3-oxidOSqualenes的合成，作为2,3-oxidOSqualene的抑制剂报道了-羊毛甾醇环化酶（OSC）。为了模拟2，3-氧化角鲨烯（2,3-OS）的自然几何形状，我们需要E-乙烯基硫化物，它是通过将硫取代的Wittig-Horner试剂（α-硫代萜烯基二苯基膦氧化物）与适当的醛缩合而制备的。通过色谱法分离出顺式和反式α-羟基二苯基膦加合物的混合物，并将顺式异构体转化为E-乙烯基硫化物。两者（6 E基）-5-和（18 Ë）-20-硫杂-2,3- OS抑制OSC从白色假丝酵母（IC 50 = 47和0.2 μ分别用M，）和大鼠肝（IC 50 = 7.7和0.32 μ分别男， ）。将它们的活性与先前合成的（6 E）-8-和（14 E）-13-thia-2,3-OSs（IC 50
• Synthesis of rac-hippospongic acid A and revision of the structure
  作者：Munetaka Tokumasu、Hiroshi Ando、Yoshikazu Hiraga、Satoshi Kojima、Katsuo Ohkata

  DOI：10.1039/a808526i

  日期：——

  rac-Hippospongic acid A of the reported structure 1 and the revised structure 2 were synthesized. The synthetic strategy of these compounds consists of homologation of (2E,6E,10E)-geranylgeraniol and (2E,6E)-farnesol, respectively, Wadsworth–Emmons reaction, and cyclization to form the tetrahydropyran ring bearing an α-methylene group on the carboxylic moiety. Spectral comparisons of the synthetic compounds 1, 2 and the natural product suggested that hippospongic acid A bears the structure of 2.

  所报道的化合物1和修订结构2的rac-Hippospongic酸A已被合成。这些化合物的合成策略包括分别对(2E,6E,10E)-香叶香叶醇和(2E,6E)-金合欢醇进行同系化反应，Wadsworth-Emmons反应，以及形成在羧基部分带有α-甲基的二氢吡喃环的环合反应。通过对比合成化合物1、2与天然产物的光谱数据，表明Hippospongic酸A具有结构2。
• Mechanistic Investigations of Two Bacterial Diterpene Cyclases: Spiroviolene Synthase and Tsukubadiene Synthase
  作者：Patrick Rabe、Jan Rinkel、Etilia Dolja、Thomas Schmitz、Britta Nubbemeyer、T. Hoang Luu、Jeroen S. Dickschat

  DOI：10.1002/anie.201612439

  日期：2017.3.1

  two diterpene cyclases from streptomycetes—one with an unknown product that was identified as the spirocyclic hydrocarbon spiroviolene and one with the known product tsukubadiene—were investigated in detail by isotope labeling experiments. Although the structures of the products were very different, the cyclization mechanisms of both enzymes proceed through the same initial cyclization reactions, before

  通过同位素标记实验详细研究了链霉菌中的两种二萜环化酶的机理，一种是未知产物，被鉴定为螺环烃螺环戊烯，另一种是已知的tsukubadiene。尽管产物的结构非常不同，但是两种酶的环化机理都是通过相同的初始环化反应进行的，然后才趋向于各个产物，这反映在酶的密切系统发育关系中。
• Lanosterol Biosynthesis: The Critical Role of the Methyl-29 Group of 2,3-Oxidosqualene for the Correct Folding of this Substrate and for the Construction of the Five-Membered D Ring
  作者：Tsutomu Hoshino、Akifumi Chiba、Naomi Abe

  DOI：10.1002/chem.201201779

  日期：2012.10.8

  Lanosterol synthase catalyzes the polycyclization reaction of (3S)‐2,3‐oxidosqualene (1) into tetracyclic lanosterol 2 by folding 1 in a chair‐boat‐chair‐chair conformation. 27‐Nor‐ and 29‐noroxidosqaulenes (7 and 8, respectively) were incubated with this enzyme to investigate the role of the methyl groups on 1 for the polycyclization cascade. Compound 7 afforded two enzymatic products, namely, 30‐norlanosterol

  羊毛甾醇合酶通过将1折叠成椅子-椅子-椅子-构象，催化（3 S）-2,3-氧化角鲨烯（1）变成四环羊毛甾醇2的多环化反应。将27-Nor-和29-Noroxidosqaulenes（分别为7和8）与该酶一起孵育，以研究1上的甲基在多环化级联反应中的作用。化合物7得到两个酶产物，即30-norlanosterol（12）和26-normalabaricatriene（13 ; 12 / 139：1），分别通过正常的椅子-椅子-椅子构造和非典型的椅子-椅子-构造构造而成。化合物8得到两个产物14和15（14 / 15 4：5），这是由正常的和不寻常的polycyclization通路通过一个椅子椅的船形椅式构象中分别产生，。值得注意的是，B形圈的麻花船结构被改为15代时在能量上很受青睐的椅子结构。令人惊讶的是14和15由一个新颖的6,6,6,6-稠合的四环系统组成，因此不同于6,6,6,5-稠