(2E,6E,10E)-3,11,15-trimethylhexadeca-2,6,10,14-tetraen-1-ol | 67858-74-6

• 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,10E)-3,11,15-trimethylhexadeca-2,6,10,14-tetraen-1-ol
• CAS: 67858-74-6
• 化学式: C₁₉H₃₂O
• 分子量: 276.462
• InChiKey: SQQAHNMSGAJJTB-PZKHUXIPSA-N

物化性质

• 沸点：
  383.1±11.0 °C(Predicted)
• 密度：
  0.881±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  20
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (2E,6E,10E)-3,11,15-trimethylhexadeca-2,6,10,14-tetraen-1-ol 在 三溴化磷 作用下， 以 乙醚 、 乙腈 为溶剂， 反应 0.75h， 生成 7-desmethylgeranylgeranyl diphosphate
  参考文献：
  名称：

  二萜底物类似物 19-nor-GGPP 揭示了二萜环化中显着的甲基效应

  摘要：

  已合成 19-正-香叶基香叶基二磷酸（除去甲基）并用 20 个二萜合酶将其转化为二萜类似物。在某些情况下，仅获得了天然酶产品的去甲基衍生物，但观察到几种酶的反应性发生显着变化。新开辟的未知骨架化合物的反应路径揭示了二萜生物合成中有趣的甲基效应。

  DOI：

  10.1002/anie.202318375
• 作为产物：
  描述：

  (E)-4-methyl-6-(phenylmethoxy)-4-hexenal 在 正丁基锂 、 氨 、 lithium 、 二异丁基氢化铝 、 甲基磺酰氯 作用下， 生成 (2E,6E,10E)-3,11,15-trimethylhexadeca-2,6,10,14-tetraen-1-ol
  参考文献：
  名称：

  Studies on taxadiene synthase: interception of the cyclization cascade at the verticillene stage and rearrangement to phomactatriene

  摘要：

  The cyclization of geranylgeranyl diphosphate ( GGDP) to taxadiene catalyzed by taxadiene synthase has been suggested to proceed in stages, involving a transient bicyclic verticillyl carbocation intermediate, which also has been proposed in the biosynthetic pathway leading to phomactatriene by marine fungi of Phoma sp. On incubation with des-7-methylGGDP, which would be expected to decrease the stability of a carbocation produced by hydride migration, taxadiene synthase produced phomactatrienes as major products. This indicates that the verticillyl carbocation was indeed formed but underwent further skeletal rearrangements, diverging from the usual pathway taken by GGDP en route to taxadiene. Products were identified using GC-MS, one- and two-dimensional NMR, and X-ray crystallography. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.03.029

文献信息

• Synthesis and carbon-13 nuclear magnetic resonance spectra of all-trans-geranylgeraniol and its nor analogs
  作者：Robert M. Coates、David A. Ley、Patricia L. Cavender

  DOI：10.1021/jo00420a003

  日期：1978.12
• Structure–Activity Relationship of Novel Menaquinone-4 Analogues: Modification of the Side Chain Affects their Biological Activities
  作者：Yoshitomo Suhara、Norika Hanada、Takashi Okitsu、Miho Sakai、Masato Watanabe、Kimie Nakagawa、Akimori Wada、Kazuyoshi Takeda、Kazuhiko Takahashi、Hiroaki Tokiwa、Toshio Okano

  DOI：10.1021/jm2013166

  日期：2012.2.23

  We synthesized new vitamin K analogues with demethylation or reduction of the double bonds of the side chain of menaquinone-4 (MK-4) and evaluated their SXR-mediated transcriptional activity as well as the extent of their conversion to MK-4. The results indicated that the analogue with the methyl group deleted at the 7' site of the side chain part affected conversion activity to MK-4. In contrast, a decrease in the number of the double bonds in the side chain moiety appeared to decrease the SXR-mediated transcriptional activity.