2,6-辛二烯醛,8-[[(1,1-二甲基乙基)二甲基甲硅烷基]氧代]-2,6-二甲基-,(2E,6E)- | 138842-85-0

• 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
• 中文名称: 2,6-辛二烯醛,8-[[(1,1-二甲基乙基)二甲基甲硅烷基]氧代]-2,6-二甲基-,(2E,6E)-
• 英文名称: (2E,6E)-8-(tert-butyldimethylsilyloxy)-2,6-dimethylocta-2,6-dienal
• 英文别名: 8-(tert-butyl-dimethyl-silanyloxy)-2,6-dimethyl-octa-2,6-dienal；8-(tert-butyldimethylsilyloxy)-2,6-dimethylocta-2,6-dienal；(2E,6E)-8-[tert-butyl(dimethyl)silyl]oxy-2,6-dimethylocta-2,6-dienal
• CAS: 138842-85-0
• 化学式: C₁₆H₃₀O₂Si
• 分子量: 282.498
• InChiKey: YLILMYQXAHBMRL-QYFSLLALSA-N

物化性质

• 沸点：
  343.3±42.0 °C(Predicted)
• 密度：
  0.885±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.88
• 重原子数：
  19
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,6-辛二烯醛,8-[[(1,1-二甲基乙基)二甲基甲硅烷基]氧代]-2,6-二甲基-,(2E,6E)- 在 sodium chlorite 、 sodium dihydrogenphosphate dihydrate 、 2-甲基-2-丁烯 作用下， 以 水 、 叔丁醇 为溶剂， 反应 15.0h， 生成
  参考文献：
  名称：

  EP2636663

  摘要：

  公开号：
• 作为产物：
  描述：

  8-hydroxygeranyl acetate 在 吡啶 、 咪唑 、 甲醇 、 potassium carbonate 、 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 为溶剂， 反应 1.75h， 生成 2,6-辛二烯醛,8-[[(1,1-二甲基乙基)二甲基甲硅烷基]氧代]-2,6-二甲基-,(2E,6E)-
  参考文献：
  名称：

  phomactin A的ABD系统的分子内形式氧杂-[3 + 3]环加成法。

  摘要：

  使用分子内形式的氧杂-oxa- [3 + 3]环加成的α，β-不饱和亚胺盐拴接到1，3-二酮上，合成了光蛋白A的ABD环。这是首次与1-oxadecalin同时形成12元环，并应提供一条通向具有挑战性的phomactin A结构的简便途径。

  DOI：

  10.1021/ol030115i

文献信息

• Stereocontrolled synthesis and configurational assignment of (R)-all-trans-11,12-dihydro-3-hydroxyretinol
  作者：Aurea Rivas、Rosana Alvarez、Angel R. de Lera

  DOI：10.1016/j.tetlet.2019.150972

  日期：2019.8

  The synthesis of (R)-all-trans-11,12-dihydro-3-hydroxyretinol and putative metabolites of the side-chain functional group has been achieved in a stereocontrolled manner via the Suzuki-Hiyama cross-coupling reaction of an enantiopure (hydroxycyclohexenyl)alkenyliodide and non-conjugated pinacolboranedienoate, which allowed the absolute configuration of this natural product to be confirmed.

  （R）-全反式-11,12-二氢-3-羟基视黄醇和侧链官能团的假定代谢物的合成是通过对映纯的Suzuki-Hiyama交叉偶联反应以立体控制的方式完成的（羟基环己烯基）烯基碘化物和非共轭松果硼烷二烯酸酯，可以确认这种天然产物的绝对构型。
• Selenium dioxide E-methyl oxidation of suitably protected geranyl derivatives—synthesis of farnesyl mimics
  作者：Ian J.S Fairlamb、Julia M Dickinson、Mathew Pegg

  DOI：10.1016/s0040-4039(01)00110-1

  日期：2001.3

  Difunctional allylic terpenes are important synthetic building blocks. Functionalisation of protected geranyl derivatives by SeO2 provides a convenient route to such compounds. The effect of the geranyl protecting group on the oxidation of the terminal E-methyl group was systematically investigated. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Didehydrogeranylgeranyl (ΔΔGG):  A Fluorescent Probe for Protein Prenylation
  作者：Xiao-hui Liu、Glenn D. Prestwich

  DOI：10.1021/ja0119144

  日期：2002.1.1

  The first intrinsically fluorescent analog of geranylgeraniol, (2E,6E,8E,10E,12E,14E)-geranylgeraniol (all-trans-DeltaDeltaGGOH.1) has been synthesized stereoselectively and shown to substitute for the geranylgeranyl (GG) moiety in prenyl transferase reactions and in protein-ligand binding assays. All-trans-DeltaDeltaGGOH 1 showed blue fluorescence in methanol, with lambdaex = 310 nm and lambdaem = 410 nm (epsilon310 = 2.4 x 104 M-1 cm-1), but was only weakly fluorescent in aqueous solution. The prenyl transferase efficiency for DeltaDeltaGGPP 2 as a substrate for yeast protein geranylgeranyl transferase (PGGTase-I) was 60% relative to that for GGPP. The binding of DeltaDeltaGG-AcCysMe 3 to the recombinant Rho GTPase dissociation inhibitor (RhoGDI) had a KD of 15.1 +/- 1.2 muM, 6-fold lower than the affinity of GG-AcCysMe. Thus, the DeltaDeltaGG moiety is a novel fluorophore suitable for studying the interaction and subcellular localization of prenylated small GTPase proteins in signaling complexes.
• Identification of presumed pheromone blend from australasian predaceous bug,Oechalia schellenbergii (Heteroptera: Pentatomidae)
  作者：Jeffrey R. Aldrich、James E. Oliver、Geoff K. Waite、Chris Moore、Rolland M. Waters

  DOI：10.1007/bf02033582

  日期：1996.4

  Oechalia schellenbergii is one of the most common predatory insects in Australia and the islands of the South Pacific. Adult males of this predaceous ''true bug'' collected during March near Gatton, Queensland, Australia, had a pair of enlarged exocrine glands opening underneath their wings that presumably produce an attractant pheromone. The two major components of the secretion are 3-methylenehexyl acetate and 9-hydroxygeranyl diacetate [2,6-dimethyl-2(E),6(E)-octadien-1,8-diol diacetate].
• Farnesyl Diphosphate Analogues with ω-Bioorthogonal Azide and Alkyne Functional Groups for Protein Farnesyl Transferase-Catalyzed Ligation Reactions
  作者：Guillermo R. Labadie、Rajesh Viswanathan、C. Dale Poulter

  DOI：10.1021/jo7017747

  日期：2007.11.1

  [Graphics]Eleven farnesyl diphosphate analogues, which contained (omega-azide or alkyne substituents suitable for bioorthogonal Staudinger and Huisgen [3 + 2] cycloaddition coupling reactions, were synthesized. The analogues were evaluated as substrates for the alkylation of peptide cosubstrates by yeast protein farnesyl transferase. Five of the diphosphates were good alternative substrates for farnesyl diphosphate (FPP). Steady-state kinetic constants were measured for the active compounds, and the products were characterized by HPLC and LC-MS. Two of the analogues gave steady-state kinetic parameters (k(cat) and K-m) very similar to those of the natural substrate.