2-methoxyazulene | 36044-37-8

• 分子结构分类: 有机化合物 - 碳氢化合物 - 不饱和烃
• 英文名称: 2-methoxyazulene
• 英文别名: 2-Methoxy-azulen；2-Methoxyazulen
• CAS: 36044-37-8
• 化学式: C₁₁H₁₀O
• 分子量: 158.2
• InChiKey: GZNQLJUHQULRFL-UHFFFAOYSA-N

物化性质

• 沸点：
  267.6±9.0 °C(Predicted)
• 密度：
  1.072±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-methoxyazulene 在 二异丁基氢化铝 、 溶剂黄146 、 三氯氧磷 作用下， 以 二氯甲烷 、 溶剂黄146 为溶剂， 生成 2-methoxy-1-[(2-methoxyazulen-1-yl)methyl]-3-[[2-methoxy-3-[(2-methoxyazulen-1-yl)methyl]azulen-1-yl]methyl]azulene
  参考文献：
  名称：

  合成[1.1.1.1]（1,3）-2-甲氧基氮杂en烯：杯芳烃的氮杂analogue类似物

  摘要：

  [1.1.1.1]（1-，3）-2-甲氧基azulenophane，杯[4]芳烃的a烯类似物是从2-甲氧基az烯开始合成的。天青石烷在室温下具有1，3-交替的构象异构体，并得到包含两个苯分子的晶体。

  DOI：

  10.1016/0040-4039(88)85225-0
• 作为产物：
  描述：

  2-Methoxy-azulen-1,3-dicarbonsaeure-dimethylester 生成 2-methoxyazulene
  参考文献：
  名称：

  Nonbenzenoid aromatic systems. XII. Synthesis of 2-, 3-, and 6-substituted 2-(1-azulyl)ethanols and their tosylate esters

  摘要：

  DOI：

  10.1021/jo00872a030

文献信息

• The formation of azulene derivatives from 2H-cyclohepta[b]furan-2-one derivatives
  作者：T. Nozoe、K. Takase、T. Nakazawa、S. Fukuda

  DOI：10.1016/s0040-4020(01)97748-8

  日期：——

  ethoxide or t-butyl-amine, giving the corresponding 1,2,3-trisubstituted azulene derivatives, respectively. The structures of these azulene derivatives are determined on the basis of chemical evidence, and spectral data. Considering the structural correlation between the starting 2H-cyclohepta[b]furan-2-ones and the azulene derivatives obtained, a reasonable reaction course, involving the heptafulvene-type

  3-乙氧基羰基-和3-乙酰基-2 H-环庚[ b ]呋喃-2-酮易于与丙二腈反应。氰基乙酰胺，氰基乙酸乙酯和丙二酸二乙酯，在乙醇钠或叔丁胺的存在下，分别得到相应的1,2,3-三取代的z并衍生物。这些a菁衍生物的结构是根据化学证据和光谱数据确定的。考虑到起始的2 H-环庚[ b ]呋喃-2-酮与所获得的氮杂环戊烯衍生物之间的结构相关性，提出了一种合理的反应过程，涉及七富烯型和二氢氮杂环戊烷型中间体，可用于从中形成氮杂环戊烯衍生物。 2 H-环庚基[ b]呋喃-2-酮。
• A New Convenient Synthesis of 1,2′-Biazulenes by Photolysis of 2-Diazo-1,3-dicyanoazulen-6(2<i>H</i>)-one with Azulene Derivatives
  作者：Shih-Jue Lin、Shuan-Ya Jiang、Tian-Chyuan Huang、Cheng-Shyan Dai、Pai-Feng Tsai、Hitoshi Takeshita、Yun-Sha -Lin、(the late) Tetsuo Nozoe

  DOI：10.1246/bcsj.70.3071

  日期：1997.12

  A photolysis of 2-diazo-1,3-dicyanoazulen-6(2H)-one in the presence of azulene derivatives in anhydrous ethyl acetate solution afforded 1,2′-biazulene derivatives, which are otherwise difficult to obtain, in good yields, nearly 90% or more. Accompanying by-products, 1,3-dicyanoazulen-6-ol and 2,5′-biazulene derivatives, were also characterized.

  2-diazo-1,3-dicyanoazulen-6(2H)-one 在 azulene 衍生物存在下在无水乙酸乙酯溶液中的光解得到 1,2'-biazulene 衍生物，否则很难以良好的产率获得，近 90% 或更多。还表征了伴随的副产物 1,3-dicyanoazulen-6-ol 和 2,5'-biazulene 衍生物。
• The Synthesis of Diethyl 2-Hydroxyazulene-1, 3-dicarboxylate from Troponoids and Some Reactions of 2-Hydroxyazulene Derivatives
  作者：Tetsuo Nozoe、Kahei Takase、Noboru Shimazaki

  DOI：10.1246/bcsj.37.1644

  日期：1964.11
• Synthesis of 2-Substituted Azulenes by Nucleophilic Substitution Reactions of 2-Haloazulene Derivatives
  作者：Tetsuo Nozoe、Shuichi Seto、Shingo Matsumura

  DOI：10.1246/bcsj.35.1990

  日期：1962.12
• Formation of Azulenequinone Derivatives from Variously Functionalized Azulenes by Bromine-oxidation
  作者：Paw-Wang Yang、Jhy-An Chen、Hidetsugu Wakabayashi、Kimio Shindo、Teruo Kurihara、Chi-Phi Wu、Masafumi Yasunami、The Late Tetsuo Nozoe

  DOI：10.1002/jccs.199700002

  日期：1997.2

  AbstractVariously functionalized 1,5‐ and 1,7‐azulenequinones were easily derived in one‐pot in 30‐50% yield from the bromine‐oxidation of 2‐methoxyazulene and 2‐methyl derivatives of 1‐cyano‐, 1‐methoxycarbonyl‐ and its 7‐isopropyl derivatives, while 1‐methoxycarbonylazulene afforded several unstable products from which we could not isolate any azulenequinones. 1‐Acetylazulene afforded 3‐bromo‐1,5‐ and ‐1,7‐azulenequinones via side‐chain brominated intermediates in high yield. 1,3‐Dichloroazulene afforded a mixture of 3‐chloro‐1,5‐ and −1,7‐azulenequinones, while 1‐fluoro‐ and 1,3‐diiodoazulene gave a mixture of 3‐bromoazulenequinones. Analogous oxidation of 1,3‐difluoroazulene produced 3‐fluoroazulenequinones, but we could not isolate them due to its instability. Hydroxy group of 2‐(3‐hydroxypropyl)azulene was intact during this quinone formation reaction.