nona-3,5,7-triyn-1-ol | 54542-18-6

• 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: nona-3,5,7-triyn-1-ol
• 英文别名: 3,5,7-nonatriyn-1-ol；Nona-3.5.7-triin-1-ol；Nona-3,5,7-triyn-1-OL
• CAS: 54542-18-6
• 化学式: C₉H₈O
• 分子量: 132.162
• InChiKey: OMYDFQNJZABHNO-UHFFFAOYSA-N

物化性质

• 熔点：
  55-57 °C
• 沸点：
  247.3±42.0 °C(Predicted)
• 密度：
  1.061±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  10
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.33
• 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：

  5-(tert-butyldiphenylsilanyloxy)pent-2-yn-1-al 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 4.0h， 生成 nona-3,5,7-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

• One-Pot Formation and Derivatization of Di- and Triynes Based on the Fritsch−Buttenberg−Wiechell Rearrangement
  作者：Thanh Luu、Yasuhiro Morisaki、Nina Cunningham、Rik R. Tykwinski

  DOI：10.1021/jo701810g

  日期：2007.12.1

  A divergent, one-pot synthesis of functionalized polyynes has been developed. Beginning with the appropriately substituted dibromoolefinic precursor, a carbenoid Fritsch−Buttenberg−Wiechell (FBW) rearrangement is used to generate the lithium acetylide of a conjugated polyyne framework, and subsequent trapping with carbon-based electrophiles provides for in situ formation of a wide range of di- and

  已经开发了一种发散的，一锅法合成的功能化多炔。从适当取代的二溴代烯烃前体开始，类胡萝卜素Fritsch-Buttenberg-Wiechell（FBW）重排用于生成共轭多炔骨架的乙炔锂，随后被碳基亲电试剂捕集，可在原位形成多种二炔和三炔。由FBW反应形成的乙炔锂也可以进行金属转移，以提供相应的锌，铜，锡或铂乙炔，导致对称和不对称共轭乙炔以及炔酮的发散形成。
• One-Pot Synthesis and Functionalization of Polyynes via Alkylidene Carbenoids
  作者：Rik Tykwinski、Thanh Luu、Yasuhiro Morisaki

  DOI：10.1055/s-2007-1000937

  日期：——

  one-pot, two-step method for the synthesis of diynes and triynes is reported. The reaction of a dibromoolefinic precursor with BuLi effects a Fritsch-Buttenberg-Wiechell rearrangement and generates a lithium acetylide intermediate, which is then trapped with a variety of electrophiles to produce substituted diynes and triynes. Alternatively, transmetalation from the lithium acetylide to give a zinc acetylide

  报道了一种合成二炔和三炔的一锅两步法。二溴烯烃前体与 BuLi 的反应会产生 Fritsch-Buttenberg-Wiechell 重排并生成乙炔锂中间体，然后用各种亲电子试剂捕获该中间体以产生取代的二炔和三炔。或者，从乙炔锂的金属转移得到乙炔锌为芳基碘化物在钯存在下通过根岸偶联形成对称或不对称的二炔和三炔提供了亲核偶联配偶体。
• Higham,C.A. et al., Journal of the Chemical Society. Perkin transactions I, 1974, p. 1991 - 1994
  作者：Higham,C.A. 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).