deca-4,6,8-triyn-1-ol | 6071-21-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: deca-4,6,8-triyn-1-ol
• 英文别名: 4,6,8-decatriyn-1-ol；deca-4,6,8-triynol；Deca-4,6,8-triin-1-ol；Decatriin-(2.4.6)-ol-(10)
• CAS: 6071-21-2
• 化学式: C₁₀H₁₀O
• 分子量: 146.189
• InChiKey: GBMVLGTXGKHYSC-UHFFFAOYSA-N

物化性质

• 熔点：
  72 °C
• 沸点：
  274.1±42.0 °C(Predicted)
• 密度：
  1.036±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  11
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  tert-butyl-pent-4-ynyloxy-diphenyl-silane 在 正丁基锂 、 barium permanganate 、 四丁基氟化铵 、 三苯基膦 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 6.0h， 生成 deca-4,6,8-triyn-1-ol
  参考文献：
  名称：

  Synthesis and Stability of a Homologous Series of Triynol Natural Products and Their Analogues

  摘要：

  A series of polyyne natural products 1, 13, and 31 and analogues 14, 21, and 22 are synthesized in six steps. The key step is a Fritsch-Buttenberg-Wiechell rearrangement in which a triyne framework is formed from the appropriate dibromoolefin precursor. Terminal conjugated triynes 13 and 14 are obtained as highly unstable products that rapidly decompose under ambient conditions. The stability of triynols increases via either the addition of methylene units (i.e., 6 -> 31 -> 1) or addition of terminal substituents (i.e., 13 -> 21 or 31).

  DOI：

  10.1021/jo061588g

文献信息

• Natural acetylenes. Part XVIII. Some allenic polyacetylenes from basidiomycetes
  作者：R. E. Bew、J. R. Chapman、Ewart R. H. Jones、B. E. Lowe、G. Lowe

  DOI：10.1039/j39660000129

  日期：——

  The isolation, characterisation, and structure determination of ten polyacetylenes, including seven new allenic-diactylenes, from five Basidiomycete fungi (Cortinellus berkeleyanus, Odontia bicolor, Flammula sapinea, Daedalea juniperina, and the unidentified fungus B285) are described. The new allenic-diacetylenes are (a) HCC·CC·CHCCH·[CH2]n·OH (n= 1, 3, and 4); (b) HCC·CC·CHCCH·CH(OH)·[CH2]n·OH (n=

  描述了十种聚乙炔的分离，表征和结构测定，其中包括五种担子菌（Cortinellus berkeleyanus，Odontia bicolor，Flamula sapinea，Daedalea juniperina和未鉴定的真菌B285）中的十种聚乙炔，其中包括七种新的烯丙基二乙炔。新的烯丙基二乙炔为（a）HC C·C C·CH C CH·[CH 2 ] n ·OH（n = 1、3和4）；（b）HC C·C C·CH C CH·CH（OH）·[CH 2 ] n ·OH（n = 2和3）；（c）HC C·C C·CH C CH·CH 2 ·CH（OH）·CH 2 ·CH2 ·OH；（d）CH 3 ·CC·CC·CHCCH·CH 2 ·CH 2 ·OH。方便地纯化二醇（b； n = 2）和（c），并检查它们的异亚丙基衍生物。
• A short and efficient synthesis of the polyacetylene natural product deca-4,6,8-triyn-1-ol
  作者：Vanessa Rocha Machado、Maique Weber Biavatti、Rick L. Danheiser

  DOI：10.1016/j.tetlet.2018.07.059

  日期：2018.9

  A practical and efficient four-step synthesis of the natural product deca-4,6,8-triyn-1-ol has been achieved beginning with (triisopropylsilyl)acetylene. This trialkyne has potential utility as a key intermediate for the total synthesis of the antitumor butenolide natural product vernoniyne.

  从（三异丙基甲硅烷基）乙炔开始，已经实现了天然产物deca-4,6,8-triyn-1-ol的实用，高效的四步合成。该三炔具有潜在的用途，可以用作抗肿瘤丁烯内酯天然产物vernoniyne的全合成的关键中间体。
• Prevost,S. et al., Bulletin de la Societe Chimique de France, 1961, p. 2171 - 2175
  作者：Prevost,S. et al.

  DOI：——

  日期：——
• Meier et al., Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1957, vol. 245, p. 1634
  作者：Meier et al.

  DOI：——

  日期：——
• Synthesis and Stability of a Homologous Series of Triynol Natural Products and Their Analogues
  作者：Thanh Luu、Rik R. Tykwinski

  DOI：10.1021/jo061588g

  日期：2006.11.1

  A series of polyyne natural products 1, 13, and 31 and analogues 14, 21, and 22 are synthesized in six steps. The key step is a Fritsch-Buttenberg-Wiechell rearrangement in which a triyne framework is formed from the appropriate dibromoolefin precursor. Terminal conjugated triynes 13 and 14 are obtained as highly unstable products that rapidly decompose under ambient conditions. The stability of triynols increases via either the addition of methylene units (i.e., 6 -> 31 -> 1) or addition of terminal substituents (i.e., 13 -> 21 or 31).