methyl 3-methylazulene-1-carboxylate | 54654-47-6

• 分子结构分类: 有机化合物 - 碳氢化合物 - 不饱和烃
• 英文名称: methyl 3-methylazulene-1-carboxylate
• 英文别名: 1-Azulenecarboxylic acid, 3-methyl-, methyl ester
• CAS: 54654-47-6
• 化学式: C₁₃H₁₂O₂
• 分子量: 200.237
• InChiKey: QLBHKORJFQBBFT-UHFFFAOYSA-N

物化性质

• 熔点：
  61-62 °C
• 沸点：
  327.4±11.0 °C(Predicted)
• 密度：
  1.126±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  methyl 3-methylazulene-1-carboxylate 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 8.0h， 以87%的产率得到3-methylazulene-1-carboxyhydrazide
  参考文献：
  名称：

  Microwave-Assisted Synthesis and Antifungal Activity of 2,5-Disubstituted-1,3,4-oxadiazoles Containing Azulene Moiety

  摘要：

  Microwave-assisted as well as conventional synthesis of 2,5-disubstituted-1,3,4-oxadiazoles containing the azulene moiety was carried out, and their antifungal activity is also reported.

  DOI：

  10.1080/00397910802654658
• 作为产物：
  描述：

  1,1-二甲氧基丙烷 、 3-(甲氧羰基)-2H-环庚[b]呋喃-2-酮 以64%的产率得到methyl 3-methylazulene-1-carboxylate
  参考文献：
  名称：

  Nozoe, Tetsuo; Wakabayashi, Hidetsugu; Ishikawa, Sumio, Heterocycles, 1990, vol. 31, # 1, p. 17 - 22

  摘要：

  DOI：

文献信息

• Synthesis and anti-ulcer activities of sodium alkylazulene sulfonates.
  作者：TAKASHI YANAGISAWA、SHUICHI WAKABAYASHI、TSUYOSHI TOMIYAMA、MASAFUMI YASUNAMI、KAHEI TAKASE

  DOI：10.1248/cpb.36.641

  日期：——

  Many derivatives of sodium alkylazulene sulfonates were newly synthesized and their antiulcer activites were examined in Shay pylorus-ligated rats. The values of lipophilicity (log P), a physicochemical parameter, of these new azulene derivatives were also examined in order to study the structure-activity relationship. The optimum value of log P which gave maximum anti-ulcer activity was about -1.0. Among the derivatives of azulene examined, 3-ethyl-7-isopropylazulene-1-sulfonic acid sodium salt (KT1-32) exhibited an extremely potent inhibitory action against Shay ulcer, and its antipeptic activity was more potent than than of guaiazulene sodium sulfonate (GAS). Furthermore, KT1-32 was extremely stable on heating as compared to GAS.

  多种新合成的钠代烷基吖啶磺酸盐衍生物在沙伊幽门结扎大鼠中进行了其抗溃疡活性的检测。此外，还研究了这些新吖啶衍生物的亲脂性（log P）这一物理化学参数，以探讨结构-活性关系。log P的最佳值，即提供最大抗溃疡活性的值，大约为-1.0。在检测的吖啶衍生物中，3-乙基-7-异丙基吖啶-1-磺酸钠盐（KT1-32）对沙伊溃疡显示出极其强大的抑制作用，其抗胃酸活性比愈创木基吖啶磺酸钠（GAS）更强。此外，与GAS相比，KT1-32在加热过程中极为稳定。
• A Versatile Synthetic Method of 1-Alkylazulenes and Azulene by the Reactions of 3-Methoxycarbonyl-2<i>H</i>-cyclohepta[<i>b</i>]furan-2-one with<i>in situ</i>Generated Enamines
  作者：Masafumi Yasunami、Shiro Miyoshi、Noriko Kanegae、Kahei Takase

  DOI：10.1246/bcsj.66.892

  日期：1993.3

  Methyl 3-alkylazulene-1-carboxylates were synthesized in high yields by the reaction of 3-methoxycarbonyl-2H-cyclohepta[b]furan-2-one with in situ generated morpholine enamines of aldehydes. Treatment of the esters with 100% phosphoric acid gave 1-alkylazulenes in excellent yields. Azulene was also synthesized in a good yield via methyl azulene-1-carboxylate with a modification of this method.

  甲基3-烷基莫I-1-羧酸酯通过3-甲氧羰基-2H-环庚[b]呋喃-2-酮与现场生成的吗啉烯胺醛反应以高产率合成。用100%磷酸处理这些酯，可以以优异的产率得到1-烷基莫I。通过这种方法的改进，以及甲基莫I-1-羧酸酯，莫I也在良好的产率下合成。
• Synthetic Photochemistry. V. Azulene Derivatives from the Photo-adducts of Methyl Acetopyruvate with Cycloheptatriene
  作者：Hitoshi Takeshita、Akira Mori

  DOI：10.1246/bcsj.47.2901

  日期：1974.11

  Two azulene derivatives, 1-methoxycarbonyl-3-methylazulene (III) and 1-methoxycarbonyl-2-methylazulene (IV), were obtained by the pyrolysis of the photoproducts of methyl acetopyruvate-cycloheptatriene. IV was understood to be derived from a subsequent photo-pinacolization of an unisolable [2+2]π photoadduct (VIII).

  通过乙酰丙酮酸甲酯-环庚三烯的光产物热解得到两种芴衍生物，1-甲氧基羰基-3-甲基芴（III）和1-甲氧基羰基-2-甲基芴（IV）。IV 被理解为源自不可溶解的 [2+2]π 光加合物 (VIII) 的后续光频哪醇化。
• Nozoe, Tetsuo; Wakabayashi, Hidetsugu; Ishikawa, Sumio, Heterocycles, 1990, vol. 31, # 1, p. 17 - 22
  作者：Nozoe, Tetsuo、Wakabayashi, Hidetsugu、Ishikawa, Sumio、Wu, Chi-Phi、Yang, Paw-Wang

  DOI：——

  日期：——
• Irvine, Nicholas M.; Majewski, Marek, Organic Preparations and Procedures International, 1995, vol. 27, # 5, p. 592 - 595
  作者：Irvine, Nicholas M.、Majewski, Marek

  DOI：——

  日期：——