cis-4-octene-2,6-diyne-1,8-diol | 180259-25-0

• 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: cis-4-octene-2,6-diyne-1,8-diol
• 英文别名: (Z)-4-octen-2,6-diyn-1,8-diol；(Z)-oct-4-en-2,6-diyne-1,8-diol
• CAS: 180259-25-0
• 化学式: C₈H₈O₂
• 分子量: 136.15
• InChiKey: ABHHGTXHTSZPPC-UPHRSURJSA-N

物化性质

• 沸点：
  259.1±35.0 °C(Predicted)
• 密度：
  1.175±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  cis-4-octene-2,6-diyne-1,8-diol 在 红铝 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以76%的产率得到(2E,4Z,6E)-octa-2,4,6-triene-1,8-diol
  参考文献：
  名称：

  An Efficient Stereocontrolled Synthesis of Di-and Triunsaturated Carbonyl Compounds

  摘要：

  omega-chlorodienals, omega-chlorodienones and 1,6-diacyl-1,3,5-hexatrienes were easily obtained from (E)- and (Z)-dichloroethylenes.

  DOI：

  10.1080/00397919608005217
• 作为产物：
  描述：

  (Z)-1,8-bis(1-ethoxyethoxy)oct-4-en-2,6-diyne 在 Amberlyst 15H 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以98%的产率得到cis-4-octene-2,6-diyne-1,8-diol
  参考文献：
  名称：

  An Efficient Stereocontrolled Synthesis of Di-and Triunsaturated Carbonyl Compounds

  摘要：

  omega-chlorodienals, omega-chlorodienones and 1,6-diacyl-1,3,5-hexatrienes were easily obtained from (E)- and (Z)-dichloroethylenes.

  DOI：

  10.1080/00397919608005217

文献信息

• Intermolecular [4 + 2] Cycloaddition of <i>o</i>-Quinodimethanes Derived from Ene−Bis(sulfinylallenes)
  作者：Shinji Kitagaki、Kumiko Katoh、Kazuhiro Ohdachi、Yuji Takahashi、Daisuke Shibata、Chisato Mukai

  DOI：10.1021/jo061014b

  日期：2006.9.1

  investigated. Benzene-bridged bis(propargyl alcohols) reacted with both electron-deficient and electron-rich olefins to give the corresponding [4 + 2] cycloadducts. Ethylene-bridged bis(propargyl alcohols) underwent similar cycloaddition with electron-deficient olefins. Construction of some heterocycles based on the newly developed sequential reaction is also described.

  研究了由烯-双（炔丙醇）和苯亚磺酰氯通过烯-双（亚磺酰基烯丙基）形成原位制备的邻喹啉甲烷的分子间[4 + 2]环加成反应。苯桥双（炔丙基醇）与缺电子和富电子的烯烃反应，生成相应的[4 + 2]环加合物。乙烯桥联的双（炔丙基醇）与缺电子的烯烃进行类似的环加成反应。还描述了基于新开发的顺序反应构建一些杂环的方法。
• Alkoxy and Enediyne Derivatives Containing 1,4-Benzoquinone Subunits—Synthesis and Antitumor Activity
  作者：Monika Kadela-Tomanek、Ewa Bębenek、Elwira Chrobak、Małgorzata Latocha、Stanisław Boryczka

  DOI：10.3390/molecules22030447

  日期：——

  4-benzoquinone subunit. This fragment occurs in three enediyne antibiotics, dynemicin A, deoxydynemicin A, and uncilamicin, which exhibit high biological activity. A series of alkoxy derivatives containing 1,4-naphthoquinone, 5,8-quinolinedione, and 2-methyl-5,8-quinolinedione moieties was synthesized. Moreover, the 1,4-benzoquinone subunit was contacted with an enediyne fragment. All obtained compounds were characterized

  生物体产生的化合物最常作为药物和制备新的半合成衍生物的原料。最大的一组天然化合物由含有 1,4-苯醌亚基的产品组成。该片段出现在三种烯二炔抗生素中，dynemicin A、deoxydynemicin A 和 uncilamicin，它们表现出很高的生物活性。合成了一系列含有 1,4-萘醌、5,8-喹啉二酮和 2-甲基-5,8-喹啉二酮部分的烷氧基衍生物。此外，1,4-苯醌亚基与烯二炔片段接触。所有获得的化合物都通过光谱和光谱方法进行表征。将所得烷烃、烯烃、炔烃和烯二炔衍生物作为抗肿瘤剂进行测试。根据 1,4-苯醌亚基的类型和使用的肿瘤细胞系，它们显示出高细胞毒活性。合成的衍生物符合利平斯基五法则并且通过血脑屏障具有低渗透性。
• Reaction of ene-bis(phosphinylallenes): [2+2] versus [4+2] cycloaddition
  作者：Shinji Kitagaki、Yuki Okumura、Chisato Mukai

  DOI：10.1016/j.tet.2006.08.083

  日期：2006.10

  Reaction of ene-bis(phosphinylallenes), derived from ene-bis(propargyl alcohols) and chlorodiphenylphosphine, was investigated. Benzene-bridged bis(phosphinylallenes) exclusively gave intramolecular [2+2] cycloadducts in the presence of dimethyl fumarate in sharp contrast to the reaction of benzene-bridged bis(sulfinylallenes), which gave the corresponding [4+2] cycloadducts. On the other hand, substituted ethylene- or five-membered heterocycle-bridged bis(phosphinylallenes) provided [4+2] cycloadducts. Reaction of benzene-bridged diallene bearing both a sulfinyl group and a phosphinyl group on the two allenyl groups was also described. (c) 2006 Elsevier Ltd. All rights reserved.
• Photoisomerization as a trigger for Bergman cyclization: Synthesis and reactivity of azoenediynes
  作者：Moumita Kar、Amit Basak、Manish Bhattacharjee

  DOI：10.1016/j.bmcl.2005.09.005

  日期：2005.12

  Cyclic enediynes 1a and 2a containing stable E-azo moiety (azoenediynes) have been synthesized. These compounds upon irradiation with long wavelength UV isomerize to the Z-compounds 1b and 2b, which can be thermally reisomerized to the Z compounds. Reactivity studies toward BC using DSC predictably indicate higher reactivity for the Z-isomers. Our studies may provide a novel way to modulate the reactivity of enediynes under thermal or photochemical conditions. (c) 2005 Elsevier Ltd. All rights reserved.
• Suffert, Jean; Raeppel, Stéphane; Raeppel, Franck, Synlett, 2000, # 6, p. 874 - 876
  作者：Suffert, Jean、Raeppel, Stéphane、Raeppel, Franck、Didier, Bruno

  DOI：——

  日期：——