5,9-Dimethyl-decatrien-(2,4-trans,8)-saeure-1 | 71385-07-4

• 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: 5,9-Dimethyl-decatrien-(2,4-trans,8)-saeure-1
• 英文别名: (2E,4E)-5,9-dimethyldeca-2,4,8-trienoic acid
• CAS: 71385-07-4
• 化学式: C₁₂H₁₈O₂
• 分子量: 194.274
• InChiKey: KHCGQZSJWAQIAB-NBBRJXQPSA-N

物化性质

• 熔点：
  62.5-64.5 °C
• 沸点：
  340.4±21.0 °C(Predicted)
• 密度：
  0.963±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5,9-Dimethyl-decatrien-(2,4-trans,8)-saeure-1 在 磷酸 、 硫酸 作用下， 生成 (E)-3-((R)-2,6,6-Trimethyl-cyclohex-2-enyl)-acrylic acid methyl ester
  参考文献：
  名称：

  DE153575

  摘要：

  公开号：
• 作为产物：
  描述：

  柠檬醛 在 乙醇 、 哌啶乙酸盐 、 silver(l) oxide 作用下， 生成 5,9-Dimethyl-decatrien-(2,4-trans,8)-saeure-1
  参考文献：
  名称：

  Kuhn; Badstuebner; Grundmann, Chemische Berichte, 1936, vol. 69, p. 102

  摘要：

  DOI：

文献信息

• Vinylcyclopropylacyl and polyeneacyl radicals. Intramolecular ketene alkyl radical additions in ring synthesis
  作者：Beno�t De Boeck、Nicola M. A. Herbert、Nicole M. Harrington-Frost、Gerald Pattenden

  DOI：10.1039/b413816n

  日期：——

  intramolecular cyclisations of their ketene alkyl radical intermediates. Under the same radical-initiating conditions the selenyl esters derived from o-vinylbenzoic acid and o-vinylcinnamic acid undergo intramolecular cyclisations producing 1-indanone and 5,6-dihydrobenzocyclohepten-7-one respectively in 60-70% yields. A tandem radical cyclisation from the alpha,beta,gamma,delta-diene selenyl ester 31 provides

  在回流的苯中用Bu（3）SnH-AIBN处理多种取代的乙烯基环丙基硒基酯，例如11，会导致相应的酰基自由基中间体，这些中间体会通过其乙烯酮烷基自由基等价物进行重排和分子内环化，从而在50-60中生成环己烯酮％ 屈服。相比之下，用Bu（3）SnH-AIBN处理共轭三烯硒烯基酯，例如32，可通过其烯酮烷基自由基中间体的分子内环化反应生成取代的2-环戊烯酮。在相同的自由基引发条件下，衍生自邻乙烯基苯甲酸和邻乙烯基肉桂酸的硒基酯进行分子内环化，分别以60-70％的产率产生1-茚满酮和5,6-二氢苯并环庚基-7-one。从alpha，beta，gamma串联串联进行的环化反应
• Stereochemical Studies on Homoterpene Biosynthesis in Higher Plants; Mechanistic, Phylogenetic, and Ecological Aspects
  作者：Andreas Gäbler、Wilhelm Boland、Ute Preiss、Helmut Simon

  DOI：10.1002/hlca.19910740820

  日期：1991.12.11

  examined plant families (Agavaceae, Asclepiadaceae, Asteraceae, Leguminosae, Magnoliaceae, and Saxifragaceae). The enzyme tolerates a wide range of structural modifications at the polar head of 3. Instead of 3, also gcranylacclone 12 and the secondary alcohol 13 can be cleaved to the homoterpene 1 and as yet unidentified carbonyl fragments. The CC bonds within the aliphatic chain of 3 seem to be essential

  在高等植物中，两个高同萜烯4,8-二甲基壬基-1,3,7-三烯（1）和4,8,12-三甲基三苯胺-1,3,7,11-teiracnc（2）来源于nerolidol （3）。或香叶菊醇（4）通过其C-骨架离子的氧化裂解而形成。反应进行时，H 8 -C（5）的3完全丢失，并正式生成C 4片段。酶的位点特异性对于迄今检查过的所有植物科（龙舌兰科，萝摩科，菊科，豆科，木兰科和虎耳草科）都是相同的。该酶在3的极性头上可耐受多种结构修饰。gcranylacclone代替312和仲醇13可以裂解为高萜1和尚未鉴定的羰基片段。脂族链3中的CC键似乎对于氧化键裂解以及底物的识别和嵌入酶的活性中心至关重要。饲料诱导的利马豆菜豆叶螨（Tetranychus urticae）感染的利马豆菜豆叶片中1和2的生物合成可能需要事先释放nerolidol（3）或geranyllinalool（4）在断裂反应之前从系统发生
• Novel Intramolecular Cyclisations Involving Ketene Radical Intermediates as an Approach to the Synthesis of Polyquinanes
  作者：Nicole M. Harrington-Frost、Gerald Pattenden

  DOI：10.1055/s-1999-2980

  日期：1999.12

  Treatment of the polyene selenyl ester 1 with Bu3SnH-AIBN leads to a concise synthesis of the diquinane 6 via a novel cyclisation involving a ketenyl radical intermediate. By contrast under the same radical initiating conditions the selenyl esters 2 and 10 produced cyclopentenone products, viz 9 and 11, and the allene substituted selenyl ester 16 led to the unusual cyclooctadienone 18.

  用 Bu3SnH-AIBN 处理多烯硒酯 1，可通过涉及酮基中间体的新颖环化反应，简便地合成二喹啉 6。相比之下，在相同的自由基引发条件下，硒酯 2 和 10 产生了环戊烯酮产物，即 9 和 11，而烯取代的硒酯 16 则产生了不常见的环辛二烯酮 18。
• v. Braun; Rudolph, Chemische Berichte, 1934, vol. 67, p. 269,279
  作者：v. Braun、Rudolph

  DOI：——

  日期：——
• 2-(Acyloxy)ethylphosphonate analogues of prenyl pyrophosphates: synthesis and biological characterization
  作者：Diana M. Cermak、David F. Wiemer、Kriste Lewis、Raymond J. Hohl

  DOI：10.1016/s0968-0896(00)00212-1

  日期：2000.12

  2-(Acyloxy)ethylphosphonate analogues of geranyl, farnesyl, and geranylgeranyl pyrophosphate have been prepared. Horner-Wadsworth-Emmons condensation of different terpene aldehydes with an unsymmetrical bisphosphonate was the key step in syntheses of the phosphonates bearing a,P-unsaturated acyloxy groups. After preparation of the respective phosphonic acids through reaction with TMSBr, both acids and esters were tested for their effects on DNA synthesis in human-derived myeloid and lymphoid leukemia cell lines. The phosphonate esters varied substantially in their ability to impair proliferation of the different cell lines, but testing against one possible target, farnesyl protein transferase (FPTase), revealed little impact at concentrations ranging up to 10 muM. Because the corresponding 2,3-dihydro compounds showed similar biological activity, conjugate addition would not appear to be involved in the toxicity. (C) 2000 Elsevier Science Ltd. All rights reserved.