6-isopropyltropolone methyl ether | 46189-88-2

• 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: 6-isopropyltropolone methyl ether
• 英文别名: 3-isopropyl-7-methoxytropone；6-isopropyl-2-methoxytropone；6-isopropyl-2-methoxy-cycloheptatrienone；2-Methoxy-6-propan-2-ylcyclohepta-2,4,6-trien-1-one
• CAS: 46189-88-2
• 化学式: C₁₁H₁₄O₂
• 分子量: 178.231
• InChiKey: DNORQMNGHAZBGW-UHFFFAOYSA-N

物化性质

• 沸点：
  309.9±31.0 °C(Predicted)
• 密度：
  1.01±0.1 g/cm3(Predicted)

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：

  6-isopropyltropolone methyl ether 、 丁炔二酸二甲酯 以63%的产率得到
  参考文献：
  名称：

  UYEHARA T.; MIYAKOSHI S.; KITAHARA Y., BULL. CHEM. SOC. JAP., 1979, 52, NO 7, 2023-2027

  摘要：

  DOI：
• 作为产物：
  描述：

  3-Iodo-2-methoxy-6-(propan-2-yl)cyclohepta-2,4,6-trien-1-one 生成 6-isopropyltropolone methyl ether
  参考文献：
  名称：

  UYEHARA T.; MIYAKOSHI S.; KITAHARA Y., BULL. CHEM. SOC. JAP., 1979, 52, NO 7, 2023-2027

  摘要：

  DOI：

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。
• 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。
• Feedback regulation of β-thujaplicin production and formation of its methyl ether in a suspension culture of Cupressus lusitanica
  作者：J Yamada

  DOI：10.1016/s0031-9422(02)00127-9

  日期：2002.7

  initial addition of beta-thujaplicin suppressed its de novo production. When beta-thujaplicin accumulation reached a certain level (ca. 40 mg/l) in the medium, the cultures seemed to cease beta-thujaplicin production. However, beta-thujaplicin productivity was restored when the beta-thujaplicin-containing medium was exchanged for fresh medium; the formation of 2-methoxy-6-(methylethyl)cyclohepta-2,4,6-trien-1-one

  Cupressus lusitanica 的悬浮细胞培养物产生β-thujaplicin，一种主要存在于柏科心材中的托酚酮。研究了控制该细胞培养系统中β-thujaplicin 积累的因素。培养物的初始细胞密度不影响 β-thujaplicin 水平，尽管最初添加 β-thujaplicin 抑制了其从头产生。当培养基中的 β- thujaplicin 积累达到一定水平 (ca. 40 mg/l) 时，培养物似乎停止了 β-thujaplicin 的产生。然而，当将含有 β-thujaplicin 的培养基更换为新鲜培养基时，β-thujaplicin 的生产力得以恢复；2-甲氧基-6-(甲基乙基)cyclohepta-2,4,6-trien-1-one，甲基化β-thujaplicin的异构体，在培养基中的形成也被观察到。
• Synthetic Photochemistry. LVII. Facile Photochemical Construction of Hexahydro-<i>as</i>-indacene Skeleton, a Carbon Framework of Ikarugamycin, from High-Pressure Diels–Alder Adducts of Tropones–Cyclopentenone
  作者：Zhi-Hong Li、Akira Mori、Nobuo Kato、Hitoshi Takeshita

  DOI：10.1246/bcsj.64.2778

  日期：1991.9

  The high-pressure Diels–Alder reaction of tropones with 2–cyclopenten-1-one afforded isomeric mixtures of adducts. Upon UV irradiation, these adducts isomerized to hexahydro-as-indacene, via [1,3] acyl migration, and tetracyclo[7.3.0.03,7.06,8]undecene derivatives through a ketene intermediate via a di-π-methane rearrangement. The former tricyclic system corresponds to the carbon skeleton of ikarugamycin

  托酮与 2-cyclopenten-1-one 的高压 Diels-Alder 反应提供了加合物的异构混合物。在紫外线照射下，这些加合物通过 [1,3] 酰基迁移异构化为六氢茚并异构化为四环 [7.3.0.03,7.06,8]十一烯衍生物，通过乙烯酮中间体通过二-π-甲烷重排。前三环系统对应于伊卡鲁霉素的碳骨架。作为副产物，获得了托酮和 1,4-环戊二烯-1-醇（2-环戊烯酮的烯醇形式）的“exo [6+4] 加合物”。