4-isopropyltropolone methyl ether | 18448-52-7

• 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: 4-isopropyltropolone methyl ether
• 英文别名: 2-methoxy-4-isopropyltropone；4-isopropyl-2-methoxytropone；2-O-methylhinokitiol；4-isopropyl-2-methoxy-cycloheptatrienone；2-methoxy-4-iso-propyltropone；4-Isopropyl-tropolon-methylether；2,4,6-Cycloheptatrien-1-one, 2-methoxy-4-(1-methylethyl)-；2-methoxy-4-propan-2-ylcyclohepta-2,4,6-trien-1-one
• CAS: 18448-52-7
• 化学式: C₁₁H₁₄O₂
• 分子量: 178.231
• InChiKey: RQUNUHQDTULGQP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 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：

  4-isopropyltropolone methyl ether 在 乙醇 、 硫酸 、 sodium ethanolate 作用下， 生成 diethyl 5-isopropylazulene-1,3-dicarboxylate
  参考文献：
  名称：

  Nozoe et al., Proceedings of the Japan Academy, 1956, vol. 32, p. 349,351

  摘要：

  DOI：
• 作为产物：
  描述：

  7-iodo-2-O-methylhinokitiol 在 palladium on activated charcoal 氢气 、 sodium acetate 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以100%的产率得到4-isopropyltropolone methyl ether
  参考文献：
  名称：

  新型氮杂氮杂烯衍生物的合成和抗过敏活性。

  摘要：

  合成了各种氮杂氮烯衍生物，并检查了它们的抗过敏活性。研究了通过在氮杂氮烯环的1-，2-或3-位引入取代基进行修饰的各种衍生物之间的构效关系。在3-位带有5-四唑基的化合物对过敏性组胺释放的抑制活性比具有其他基团（CN，COOH和CHO）的相应化合物更有效。在2-位被氨基，叠氮化物和羧甲基氨基取代的化合物表现出很强的抑制活性。在1位具有各种苯基烷基的化合物比具有其他取代基的化合物具有更高的活性。在氮杂氮烯环的1-，2-或3-位带有取代基的化合物中，

  DOI：

  10.1248/cpb.42.2491

文献信息

• Synthesis and the Spectral Analysis of 4- and 6-[1-Acetamido-3-(3,4,5-trimethoxyphenyl)propyl]-2-methoxytropones(B-Ring-open Analogues of Colchicine)
  作者：Hiroshi Yamamoto、Atsushi Hara、Saburo Inokawa、Tetsuo Nozoe

  DOI：10.1246/bcsj.56.3106

  日期：1983.10

  The treatment of 4-[1-acetamido-3-(3,4,5-trimethoxyphenyl)propyl]tropolone with ethereal diazomethane gave the 6- and 4-substituted title compounds in 51 and 38% yields, respectively. The 270-MHz 1H-NMR spectral analysis performed on these compounds, colchicine, and two methyl ethers of hinokitiol permits unequivocal assignment of the position of the C-substituent on these 2-methoxytropone rings. Attempts were made to effect the direct B-ring closure of these intermediates and 4-[1-acetamido-3-(3,4,5-trimethoxyphenyl)propyl]-5-aminotropolone using various oxidizing reagents.

  以4-[1-乙酰胺基-3-(3,4,5-三甲氧基苯基)丙基]托烷酮为原料，与乙醚二甲基甲烷反应，分别得到了6-取代和4-取代的目标化合物，产率为51%和38%。对这些化合物、秋水仙碱以及两个硫靑醇甲醚进行了270 MHz的1H-NMR光谱分析，明确了这些2-甲氧基托烷酮环上C-取代基的位置。尝试使用各种氧化剂直接实现这些中间体和4-[1-乙酰胺基-3-(3,4,5-三甲氧基苯基)丙基]-5-氨基托烷酮的B环闭合。
• Preparation of Polyacetoxytropones and Polyhydroxytropolones by Acetolysis and Hydrolysis of Halotroponoids by Acetyl Trifluoroacetate with Exhaustive Displacement of Halogens on the Tropone Ring. Predominant Formation of Reductive Acetolysates from Fully-Substituted Tropones
  作者：Hitoshi Takeshita、Akira Mori、Tomoyuki Kusaba、Hiroyasu Watanabe

  DOI：10.1246/bcsj.60.4325

  日期：1987.12

  acetic acid-mediated reduction of intermediary formed acetoxy-p-tropoquinone equivalents. A couple of 2,7-unsubstituted 3,4-diacetoxytropones were deduced to have cyclized 1,3-dioxole structures, 2-acetoxy-2-methyl-5H-cyclohepta-1,3-dioxol-5-ones. An acetolysis of the brominated 5-isopropyltropolones furnished an acetylated by-product, 2,3,7-triacetoxy-5-(1,1-dimethyl-2-oxopropyl)tropone, which might be

  通过将相应的卤代托品酮或多卤代托品酮与乙酰基三氟乙酸酯进行乙酰水解，然后进行乙酸水解，可以高产率地制备二、三和四羟基托品酮。然而，使用相同的处理获得具有完全取代的乙酰氧基卤代酮的六乙酰氧托酮主要产生比预期更少的取代乙酰氧托酮；已证明形成机制涉及乙酸介导的中间形成的乙酰氧基-对-原苯醌等效物的还原。一些 2,7-未取代的 3,4-diacetoxytropones 被推导出具有环化的 1,3-dioxole 结构，2-acetoxy-2-methyl-5H-cyclohepta-1,3-dioxol-5-ones。溴化 5-异丙基托酚酮的乙酰化提供乙酰化副产物 2,3,7-三乙酰氧基-5-(1,1-二甲基-2-氧代丙基)托酮，
• INTENTIONAL SYNTHESES OF UTAHIN, A CONIFER CONSTITUENT OF A C₂₀-DITROPONOFURAN, VIA THE OXIDATIVE CONDENSATION
  作者：Hitoshi Takeshita、Tomoyuki Kusaba、Akira Mori

  DOI：10.1246/cl.1983.1371

  日期：1983.9.5

  Utahin, previously characterized as a constituent of Juniperus utahensis, has been prepared by a biomimetic oxidation of hinokitiol in addition to the coupling reactions of 4-isopropyl-p-tropoquinone with 5-hydroxyhinokitiol.

  Utahin，以前被表征为杜松的一种成分，除了 4-异丙基-p-原苯醌与 5-羟基扁柏醇的偶联反应外，还通过桧醇的仿生氧化制备。
• Enantioselective Photoreaction of 4-Isopropyltropolone Methyl Ether in Inclusion Crystals with Optically Active Host Compounds
  作者：Koichi Tanaka、Ryoji Nagahiro、Zofia Urbanczyk-Lipkowska

  DOI：10.1021/ol015857v

  日期：2001.5.1

  Upon photoirradiation of a 2:1:1 inclusion complex of (−)-1, 4-isopropyltropolone methyl ether (3b) and chroloform, optically active photocyclization products (−)-6a and (−)-7a were obtained in 96% and 90% ee, respectively.

  在 (-)-1, 4-异丙基托酚酮甲醚 (3b) 和三氯甲烷的 2:1:1 包合物的光照射下，获得 96% 的光学活性光环化产物 (-)-6a 和 (-)-7a，分别为 90% ee。
• Azaazulene compounds which are useful as antiallergic and
  申请人：Kaken Pharmaceutical Co., Ltd.

  公开号：US05013736A1

  公开（公告）日：1991-05-07

  An azaazulene derivative having the general formula (I): ##STR1## wherein R.sup.1 is hydrogen atom or isopropyl group; the bond C N between C at the 2-position and N at the 1-position is single bond or double bond; when the bond C N is single bond, R.sup.2 is 5-tetrazolyl group, R.sup.3 is taken together with carbon atom to form carbonyl group at the 2-position, and R.sup.4 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: ##STR2## in which W is single bond or carbonyl group, oxygen atom, sulfur atom or --CH.dbd.CH--, n is an integer of 1 to 6, and R.sup.1', R.sup.2' and R.sup.3' 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 C N is double bond, N at the 1-position has no substituent R.sup.4, R.sup.2 is cyano group, and R.sup.3 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.

  具有通式（I）的azaazulene衍生物：##STR1## 其中，R1是氢原子或异丙基基团；C位于2-位置和N位于1-位置之间的C N键是单键或双键；当C N键是单键时，R2是5-四唑基基团，R3与碳原子共同形成2-位置的羰基基团，R4是氢原子，具有1至18个碳原子的烷基基团，较低的烯基基团，在碳链中具有氧原子或硫原子的较低烷基基团，具有卤原子或氰基的较低烷基基团，具有杂环芳香环的较低烷基基团，二苯基较低烷基基团或具有通式的烷基基团：##STR2## 其中，W是单键或羰基基团，氧原子，硫原子或--CH.dbd.CH--，n是1至6的整数，R1'，R2'和R3'相同或不同，每个是氢原子，卤原子，较低的烷基基团，较低的烷氧基基团，三氟甲基基团，羟基基团，较低的烷氧羰基基团，羧基基团，乙酰基基团或氰基；当C N键是双键时，1-位置的N没有取代基R4，R2是氰基，R3是氨基或其盐，叠氮基，二苯基较低烷基氨基基团，取代苯氨基基团，取代哌嗪基团，取代吡啶基团，氨基酸残基通过N末端基团与羧基基团或较低烷基酯结合，或其盐，或具有环状的烷基氨基基团，或其盐。该化合物可用作抗过敏剂和抗炎剂的活性成分，并具有组胺释放抑制活性，5-脂氧酶抑制活性，平滑肌气管松弛活性和卡拉胶水肿抑制活性，并且可用作预防和治疗支气管哮喘，过敏性鼻炎，过敏性结膜炎，荨麻疹，特应性皮炎，其他炎症性疾病等的药物。