5-isopropyl-2-methoxytropolone | 18448-53-8

• 分子结构分类: 有机化合物 - 碳氢化合物衍生物 - 环庚三烯酮
• 英文名称: 5-isopropyl-2-methoxytropolone
• 英文别名: 5-isopropyl-2-methoxytropone；5-isopropyl-2-methoxy-cycloheptatrienone；5-Isopropyl-2-methoxy-cycloheptatrienon；γ-Thujaplicin-methylaether；5-Isopropyl-tropolon-methylether；5-Isopropyl-2-methoxytropon；2-Methoxy-5-(propan-2-yl)cyclohepta-2,4,6-trien-1-one；2-methoxy-5-propan-2-ylcyclohepta-2,4,6-trien-1-one
• CAS: 18448-53-8
• 化学式: C₁₁H₁₄O₂
• 分子量: 178.231
• InChiKey: AHYLHLAMEMPLJC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 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：

  5-isopropyl-2-methoxytropolone 在 氨 作用下， 生成 氨甲酸,(1-乙基戊基)-,甲基酯(9CI)
  参考文献：
  名称：

  Nozoe et al., Proceedings of the Japan Academy, 1954, vol. 30, p. 482,484

  摘要：

  DOI：
• 作为产物：
  描述：

  2-羟基-5-异丙基-2,4,6-环庚三烯-1-酮 生成 5-isopropyl-2-methoxytropolone
  参考文献：
  名称：

  NAULT, J., WOOD SCI. AND TECHNOL., 21,(1987) N 4, 311-316

  摘要：

  DOI：

文献信息

• Cyclohepta[<i>b</i>][1,4]benzothiazines and Their Diazine Analogues. 2. Formation and Properties of Cyclohepta[<i>b</i>]quinoxalines
  作者：Kimio Shindo、Sumio Ishikawa、Tetsuo Nozoe

  DOI：10.1246/bcsj.62.1158

  日期：1989.4.15

  2-Chloro- or 2-methoxytropone reacts with o-phenylenediamine to give 2-(o-aminoanilino)tropone, which upon heating provides 6H-cyclohepta[b]quinoxaline (10a). Upon acidification, 10a reversibly gives a green cation, 9a. 10a is easily converted, especially under basic conditions, into the oxidative dimer 16a, which reproduces 9a by reduction with Zn in acetic acid. The isopropyl derivatives of these compounds are prepared by the same method from 5-isopropyl-2-methoxytropone. The 5-methyl (21a) and 5,11-dimethyl derivatives 23 are made by the reaction of 2-chloro- or 2-methoxytropone with N-methyl- and N,N′-dimethyl-o-phenylenediamines. However, the methylation of 21a with methyl fluorosulfate affords 5,11-dihydro-8,11-dimethyl-6H-cyclohepta[b]quinoxaline-5,6-sultone. H2O2 oxidation of 10a mainly gives 16a in addition to a small quantity of 6H-cyclohepta[b]quinoxalin-6-one. Compound 21a is stable under basic conditions, but 23 rearranges under alkaline conditions to give, among other unidentified products, N-methyl-N-[o-(methylamino)phenyl]benzamide and 5,10-dihydro-5,10-dimethyl-2-phenazinecarbaldehyde. Reactions of title compounds with alkali and hydrogen peroxide are compared with those of O- and S-analogues.

  2-氯或2-甲氧基脱氢松香与邻苯二胺反应生成2-(邻氨基苯基氨基)脱氢松香，随着加热生成6H-环七[b]喹喏啉(10a)。在酸性环境下，10a 可逆地生成绿色阳离子9a。10a 易于转化，特别是在碱性条件下，生成氧化二聚体16a，16a通过与醋酸中的Zn还原可再生9a。这些化合物的异丙基衍生物是通过5-异丙基-2-甲氧基脱氢松香用同样的方法制备的。5-甲基(21a)和5,11-二甲基衍生物23是通过2-氯或2-甲氧基脱氢松香与N-甲基和N,N'-二甲基邻苯二胺反应制得的。然而，用氟甲基硫酸盐对21a进行甲基化反应则得到5,11-二氢-8,11-二甲基-6H-环七[b]喹喏啉-5,6-磺酸酯。10a的H2O2氧化反应主要生成16a，外加少量的6H-环七[b]喹喏啉-6-酮。化合物21a在碱性条件下稳定，但23在碱性条件下发生重排，生成包括N-Methyl-N-[o-(甲基氨基)苯基]苯胺和5,10-二氢-5,10-二甲基-2-苯嗪羧醛在内的其他未鉴定产品。标题化合物与碱和氢过氧化物的反应与O-和S-类比的反应进行比较。
• meta-Photoaddition reactions of 2-chloro-, 2,5-dichloro-, and 2-halo-5-isopropyl-tropones with 9,10-dicyanoanthracene
  作者：Akira Mori、Hiroki Yokoo、Toshihide Hatsui

  DOI：10.1016/j.tet.2004.07.049

  日期：2004.9

  Photoreactions of 2-halotropones with the excited 9,10-dicyanoanthracene gave a meta-adduct and substitution products occurred at the C-2 position of troponoids. The mechanism of the meta-adduct was proved by the product analysis of the reaction of 3,7-dideuterio-2-bromo-5-isopropyltropone and 9,10-dicyanoanthracene. In the photoreaction of 2-chloro-5-isopropyltropone and 9,10-dicyanoanthracene in

  2-卤代酮与激发的9,10-二氰基蒽发生光反应，生成间位加合物，取代产物出现在肌钙蛋白的C-2位置。通过3,7-二氘-2-溴-2-溴-5-异丙基丙酮与9,10-二氰基蒽的反应的产物分析证明了间加合物的机理。在苯和甲醇的混合溶剂中，2-氯-5-异丙基丙酮和9,10-二氰基蒽的光反应中，获得了带有二苯并-2-氧杂双环[3.2.2]壬烷体系的苯甲醛，以支持[它们之间的[8 + 4]环加成反应。
• Azaazulene derivative, process for preparing the same, and antiallergic agent and antiinflammatory agent containing the same
  申请人：Kaken Pharmaceutical Co., Ltd.

  公开号：EP0376223A2

  公开（公告）日：1990-07-04

  An azaazulene derivative having the general formula (I): wherein R1 is hydrogen atom or isopropyl group; the bond between C at the 2-position and N at the 1-position is single bond or double bond; when the bond is single bond, R2 is 5-tetrazolyl group, R3 is taken together with carbon atom to form carbonyl group at the 2-position, and R4 is hydrogen atom, an alkyl group having 1 to 18 carbon atoms, a lower alkenyl group, a lower alkyl group having oxygen atom or sulfur atom in carbon chain, a lower alkyl group having a halogen atom or cyano group, a lower alkyl group having heteroaromatic ring, a diphenyl lower alkyl group, or a lower alkyl group having hydrocarbon-aromatic ring with the general formula: in which W is,single bond or carbonyl group, oxygen atom, sulfur atom or -CH = CH-, n is an integer of 1 to 6, and R' , R2 and R3 are the same or different and each is hydrogen atom, a halogen atom, a lower alkyl group, a lower alkoxyl group, trifluoromethyl group, hydroxyl group, a lower alkoxycarbonyl group, carboxyl group, acetyl group or cyano group; when the bond is double bond, N at the 1-position has no substituent R4, R2 is cyano group, and R3 is amino group or a salt thereof, azido group, a diphenyl lower alkyl amino group, a substituted phenyl amino group, a substituted piperazinyl group, a substituted homopiperazinyl group, an amino acid residue bonded by N terminal group in which C terminal group is carboxyl group or a lower alkyl ester thereof, or a lower alkyl amino group which may have an alkyl amino group that may be cyclic one, or a salt thereof, which is useful as an active ingredient of an antiallergic agent and an antiinflammatory agent and has also an inhibitory activity against histamine release, 5-lipoxygenase inhibiting activity, relaxing activity of smooth musculus trachealis and inhibitory activity against carrageenin edema, and further, is useful as medicine for prevention and treatment of bronchial asthma, allergic coryza, allergic conjunctivitis, urticaria, atopic dermatitis, other inflammatory diseases or the like.

  一种具有通式(I)的氮杂环戊烯衍生物： 其中 R1 为氢原子或异丙基；位于 2 位的 C 与位于 1 位的 N 之间的键为单键或双键 在 2 位的 C 与 1 位的 N 之间的键是单键或双键；当键是单键时，R2 是 5-四唑基，R3 与 1 位的 N 之间的键是单键或双键。 R4为氢原子、具有 1 至 18 个碳原子的烷基、低级烯基、在碳链中具有氧原子或硫原子的低级烷基、具有卤素原子或氰基的低级烷基、具有杂芳香环的低级烷基、二苯基低级烷基或具有烃-芳香环的低级烷基，通式如下： 其中，W 是单键或羰基、氧原子、硫原子或 -CH = CH-，n 是 1 至 6 的整数，R'、R2 和 R3 相同或不同，并且各自是氢原子、卤素原子、低级烷基、低级烷氧基、三氟甲基、羟基、低级烷氧基羰基、羧基、乙酰基或氰基；当键 为双键时，位于 1 位的 N 没有取代基 R4，R2 为氰基，R3 为氨基或其盐、叠氮基、二苯基低级烷基氨基、取代的苯基氨基、取代的哌嗪基、取代的均哌嗪基、由 N 末端基团（其中 C 末端基团为羧基或其低级烷基酯）键合的氨基酸残基、或低级烷基氨基（其烷基氨基可以是环状的）或其盐、它可作为抗过敏剂和抗炎剂的有效成分，还具有抑制组胺释放的活性、抑制 5-脂氧合酶的活性、松弛气管平滑肌的活性和抑制卡拉胶水肿的活性，还可作为预防和治疗支气管哮喘、过敏性咽喉炎、过敏性结膜炎、荨麻疹、特应性皮炎、其他炎症或类似疾病的药物。
• Erdtman; Gripenberg, Acta Chemica Scandinavica (1947), 1948, vol. 2, p. 625,635
  作者：Erdtman、Gripenberg

  DOI：——

  日期：——
• Sato, Tohoku Daigaku Hisui Yoeki Kagaku Kenkyusho Hokoku, 1959, vol. 8, p. 47,62
  作者：Sato

  DOI：——

  日期：——