(2E,6E)-2,6-dimethyl-8-hydroxy-2,6-octadienyl propargyl ether | 109334-38-5

• 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: (2E,6E)-2,6-dimethyl-8-hydroxy-2,6-octadienyl propargyl ether
• 英文别名: (2E,6E)-3,7-dimethyl-8-(prop-2-yn-1-yloxy)octa-2,6-dien-1-ol；2,6-Octadien-1-ol, 3,7-dimethyl-8-(2-propynyloxy)-, (E,E)-；(2E,6E)-3,7-dimethyl-8-prop-2-ynoxyocta-2,6-dien-1-ol
• CAS: 109334-38-5
• 化学式: C₁₃H₂₀O₂
• 分子量: 208.301
• InChiKey: WWMCHUKROQKBLP-SWZPTJTJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  15
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2E,6E)-2,6-dimethyl-8-hydroxy-2,6-octadienyl propargyl ether 在 4-二甲氨基吡啶 、 正丁基锂 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 21.0h， 生成 4-hydroxy-2-butynyl(2E,6E)-2,6-dimethyl-8-<(tert-butyldimethylsilyl)oxy>-2,6-octadienyl ether
  参考文献：
  名称：

  Synthesis of cembrane natural products via [2,3] Wittig ring contraction of propargylic ethers

  摘要：

  DOI：

  10.1021/jo00226a026
• 作为产物：
  描述：

  (2E,6E)-2,6-dimethyl-8-<(tert-butyldimethylsilyl)oxy>-2,6-octadienyl propargyl ether 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 以94%的产率得到(2E,6E)-2,6-dimethyl-8-hydroxy-2,6-octadienyl propargyl ether
  参考文献：
  名称：

  Farnesyl Diphosphate Analogues with ω-Bioorthogonal Azide and Alkyne Functional Groups for Protein Farnesyl Transferase-Catalyzed Ligation Reactions

  摘要：

  [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.

  DOI：

  10.1021/jo7017747

文献信息

• Synthesis and interaction of terminal unsaturated chemical probes with Mycobacterium tuberculosis CYP124A1
  作者：Luz Díaz-Storani、Anaelle A. Clary、Diego M. Moreno、María Sol Ballari、Exequiel O.J. Porta、Andrea B.J. Bracca、Jonathan B. Johnston、Guillermo R. Labadie

  DOI：10.1016/j.bmc.2021.116304

  日期：2021.8

  other hand, the C15-ω-ene analog interacts with the ferric heme by displacing the bound water that generates a typical Type I binding spectrum. We were unable to detect P450-mediated oxidation of these probes following extended incubations with CYP124A1 in our reconstituted assay system, whereas a control reaction containing farnesol was converted to ω-hydroxy farnesol under the same conditions. To understand

  合成了一系列带有末端链烯基和炔基的 C15-C20 异戊二烯基衍生物作为来自结核分枝杆菌的甲基支化脂质 ω-羟化酶 CYP124A1 的可能底物. 每种化合物与酶活性位点的相互作用使用紫外-可见光谱进行表征。我们发现 C10 和 C15 类似物分别以相似的亲和力结合相应的母体 C10 和 C15 底物香叶醇和法呢醇。三种类似物（C10-ω-ene、C10-ω-yne、C15-ω-yne）通过与三价铁血红素的氧原子配位与血红素铁的近侧相互作用，如典型的 Type- IA结合光谱。另一方面，C15-ω-ene 类似物通过置换结合水与三价铁血红素相互作用，产生典型的 I 型结合光谱。在我们重构的分析系统中与 CYP124A1 延长孵育后，我们无法检测到 P450 介导的这些探针的氧化，而含有法呢醇的对照反应在相同条件下转化为 ω-羟基法呢醇。为了了解缺乏可检测的氧化，我们探索了类似物作为基于机制
• MARSHALL, J. A.;JENSON, T. M.;DEHOFF, B. S., J. ORG. CHEM., 52,(1987) N 17, 3860-3866
  作者：MARSHALL, J. A.、JENSON, T. M.、DEHOFF, B. S.

  DOI：——

  日期：——
• 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.
• Synthesis of cembrane natural products via [2,3] Wittig ring contraction of propargylic ethers
  作者：James A. Marshall、Todd M. Jenson、Bradley S. DeHoff

  DOI：10.1021/jo00226a026

  日期：1987.8