5-isopropylidene-3,8-dimethyl-1(5H)-azulenone | 111873-87-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 5-isopropylidene-3,8-dimethyl-1(5H)-azulenone
• 英文别名: 1(5H)-Azulenone, 3,8-dimethyl-5-(1-methylethylidene)-；3,8-dimethyl-5-propan-2-ylideneazulen-1-one
• CAS: 111873-87-1
• 化学式: C₁₅H₁₆O
• 分子量: 212.291
• InChiKey: BHLYQNMLGRQFKV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  5-isopropylidene-3,8-dimethyl-1(5H)-azulenone 、 氧气 以8%的产率得到
  参考文献：
  名称：

  MATSUBARA, YOSHIHARU;MATSUI, SHUICHI;TAKEKUMA, SHIN-ICHI;QUO, YAN PIN;YAM+, BULL. CHEM. SOC. JAP., 62,(1989) N, C. 2040-2044

  摘要：

  DOI：
• 作为产物：
  描述：

  愈创奥 在 lithium aluminium tetrahydride 作用下， 反应 12.0h， 生成 5-isopropylidene-3,8-dimethyl-1(5H)-azulenone
  参考文献：
  名称：

  1-Hydroxyazulene and 3-hydroxyguaiazulene: Synthesis and their properties

  摘要：

  DOI：

  10.1016/s0040-4039(00)70653-8

文献信息

• A Facile Preparation of 5-Isopropylidene-3,8-dimethyl-1(5<i>H</i>)-azulenone and Its Crystal Structure
  作者：Shin-ichi Takekuma、Syougo Jyoujima、Masato Sasaki、Takuya Matsumoto、Hideo Fukunaga、Hideko Takekuma、Hiroshi Yamamoto

  DOI：10.1246/bcsj.75.151

  日期：2002.1

  Oxidation of 5,5′-biguaiazulene-3,3′(5H,5′H)-dione (2) with 2,3-dichloro-5,6-dicyano-p-benzoquinone (DDQ) in CH2Cl2 at 25 °C under aerobic conditions rapidly gives the title compound, 5-isopropylidene-3,8-dimethyl-1(5H)-azulenone (4), in 52% isolated yield. The crystal structure of 4 is reported as the first example for azulenequinonemethides.

  在有氧条件下，于 25 °C 的 CH2Cl2 溶液中，用 2,3-二氯-5,6-二氰基对苯醌（DDQ）氧化 5,5′-biguazulene-3,3′(5H,5′H)-dione(2)，可迅速得到标题化合物 5-异亚丙基-3,8-二甲基-1(5H)-氮杂烯酮（4），分离收率为 52%。据报道，4 的晶体结构是偶氮喹啉醚类化合物的第一个实例。
• 6-(3-Guaiazulenyl)-5-isopropyl-3,8-dimethyl-1(6<i>H</i>)-azulenone and Its Norcaradiene-Isomer. Key Intermediates for Novel Intermolecular One-Carbon Transfer in Autoxidation of Guaiazulene
  作者：Yoshiharu Matsubara、Shin-ichi Takekuma、Hiroshi Yamamoto、Tetsuo Nozoe

  DOI：10.1246/cl.1987.455

  日期：1987.3.5

  Autoxidation of guaiazulene either at 85 °C in N,N-dimethylformamide-0.5 M sulfuric acid or at 25–35 °C on the surface of a filter paper yielded, together with other products, the two title compounds which were shown to be in equilibrium and to constitute important intermediates for the intermolecular one-carbon transfer reactions frequently observed during autoxidation of many azulenic hydrocarbons.

  愈创蓝油烯在 85 °C 在 N,N-二甲基甲酰胺-0.5 M 硫酸中或在 25–35 °C 在滤纸表面上自动氧化，与其他产物一起产生两种标题化合物，它们在平衡并构成在许多天青烃的自氧化过程中经常观察到的分子间一碳转移反应的重要中间体。
• An Efficient Preparation and Reactions of [5,6′-Biguaiazulene]-3,3′(5<i>H</i>,6′<i>H</i>)-dione and 5-Isopropylidene-3,8-dimethyl-1(5<i>H</i>)-azulenone: Key Intermediates for the Autoxidation Products of Guaiazulene
  作者：Yoshiharu Matsubara、Shuichi Matsui、Shin-ichi Takekuma、Yan Pin Quo、Hiroshi Yamamoto、Tetsuo Nozoe

  DOI：10.1246/bcsj.62.2040

  日期：1989.6

  Oxidation of guaiazulene (1) with peracetic acid in hexane at 25 °C afforded as high as an 80% yield of the title biguaiazulenedione (12), which upon heating at 60 °C under nitrogen gave the title 1-azulenone (13) quantitatively. Oxidation of 12 and 13 was studied under various conditions, and these compounds were shown to be highly important key intermediates for a large number of the complex products obtained by autoxidation of 1.

  在己烷中于 25 °C 下用过乙酸氧化愈创蓝油烯 (1)，得到产率高达 80% 的标题双愈创蓝油烯二酮 (12)，在氮气下于 60 °C 加热时定量得到标题 1-薁酮 (13) 。在各种条件下研究了12和13的氧化，这些化合物被证明是1自氧化得到的大量复杂产物的非常重要的关键中间体。
• X-Ray Crystal Structure of Guaiazulenequinone and the Structures of Two New Guaiazulenone Derivatives
  作者：Hideko Takekuma、Shin-ichi Takekuma、Yoshiharu Matsubara、Hiroshi Yamamoto、Tetsuo Nozoe

  DOI：10.1246/cl.1995.465

  日期：1995.6

  The first X-ray crystallographic analysis on azulenequinones is reported for 3,5-guaiazulenedione. Two unique azulenone derivatives, 3a-hydroxy-3(3aH)-guaiazulenone and 2,2′-bi-3,5-guaiazulenedione, are obtained by the autoxidation of 5,5′-biguaiazulene-3,3′(5H,5′H)-dione in pyridine at 25 °C. The possible reaction pathways for these azulenone formation are discussed.

  首次对薁醌进行 X 射线晶体学分析，报道了 3,5-愈创木薁二酮。通过 5,5'-双愈创蓝酮-3,3'(5H,5)的自动氧化获得两种独特的薁酮衍生物，3a-羟基-3(3aH)-愈创蓝酮和 2,2'-双-3,5-愈创蓝二酮'H)-二酮吡啶溶液，25 °C。讨论了这些薁酮形成的可能反应途径。
• TOYONOBU, ASAO;SHUNJI, ITO;NOBORU, MORITA, TETRAHEDRON LETT., 30,(1989) N8, C. 6693-6696
  作者：TOYONOBU, ASAO、SHUNJI, ITO、NOBORU, MORITA

  DOI：——

  日期：——