5-iodo-2-methoxytropone | 343962-18-5

• 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-iodo-2-methoxytropone
• 英文别名: 5-Iodo-2-methoxycyclohepta-2,4,6-trien-1-one
• CAS: 343962-18-5
• 化学式: C₈H₇IO₂
• 分子量: 262.047
• InChiKey: OFAKLONUAVDVON-UHFFFAOYSA-N

物化性质

• 沸点：
  315.9±42.0 °C(Predicted)
• 密度：
  1.80±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 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-iodo-2-methoxytropone 在 四丁基氟化铵 、 palladium diacetate 、 三苯基膦 作用下， 以 四氢呋喃 、 水 为溶剂， 生成 2-Methylsulfanyl-5-(2,3,4-trimethoxy-phenyl)-cyclohepta-2,4,6-trienone
  参考文献：
  名称：

  Discovery of structurally simplified analogs of colchicine as an immunosuppressant

  摘要：

  We have discovered a new class of colchicine-derived therapeutic agents for immune diseases including rejection of organ-transplantation and autoimmune disease. Compound 2, which had been developed to overcome poor pharmacokinetic properties of compound 1, a first-generation colchicine analog, turned out to show toxicity such as intestinal toxicity and loss of weight during in vivo tests. The deletion of 7-carboxamide group and middle ring-truncation in colchicine allowed us to have structurally simplified analogs with strong immunosuppressive activity. Herein, we report non-alkaloid tricyclic compound 7 and 12 as immunosuppressants which exhibited a strong immunosuppressive in vivo efficacy on the T-dependent antibody response, the Zymosan A-induced arthritis model and the Carrageenan-induced edema model. Compound 7 and 12 revealed less toxicity than the previous lead compound 2, and their minimum lethal doses (MLD) were proved to exceed 100 mg/kg. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.05.007
• 作为产物：
  描述：

  环庚三烯酚酮 在 palladium on activated charcoal 盐酸 、 氢气 、 sodium nitrite 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， -20.0~55.0 ℃ 、99.97 kPa 条件下， 反应 4.0h， 生成 5-iodo-2-methoxytropone
  参考文献：
  名称：

  改进和高度通用的 5-Aryltropones 合成

  摘要：

  摘要 5-碘-2-甲氧托酮在钯(0)催化偶联反应中与多种芳基硼酸的使用显着提高了空间和电子多样化系列新型5-芳基托酮的反应产率和时间。此外，所需的 5-碘-2-甲氧托酮可以以优异的收率方便地合成。

  DOI：

  10.1081/scc-200066658

文献信息

• Novel Retinoidal Tropolone Derivatives. Bioisosteric Relationship of Tropolone Ring with Benzoic Acid Moiety in Retinoid Structure.
  作者：Masayuki EBISAWA、Kiminori OHTA、Emiko KAWACHI、Hiroshi FUKASAWA、Yuichi HASHIMOTO、Hiroyuki KAGECHIKA

  DOI：10.1248/cpb.49.501

  日期：——

  Several tropolone derivatives (4-7) were designed as novel retinoids on the assumption that the tropolone ring may mimic the benzoic acid moiety in retinoid structures, such as Am80 (2). Among the synthesized compounds, 5-[2-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)ethynyl]tropolone (7a) showed moderate potency as a differentiation-inducer of HL-60 cells. The activities of the tropolones were

  假定托酚酮环可模仿类维生素A结构中的苯甲酸部分，例如Am80（2），则将几种托酚酮衍生物（4-7）设计为新型维甲酸。在合成的化合物中，5- [2-（5,6,7,8-四氢-5,5,8,8-四甲基-2-萘基）乙炔基] tropolone（7a）具有中等强度，可作为诱导分化的化合物HL-60细胞。在RXR激动剂（类维生素A增效剂）HX630的存在下，对营养素的活性大大增强。
• Acid- and base-induced conformational alterations of N-aryl-N-troponyl amides
  作者：Ai Ito、Masanori Sato、Ryu Yamasaki、Iwao Okamoto

  DOI：10.1016/j.tetlet.2015.12.048

  日期：2016.1

  We have investigated acid- and base-induced conformational alterations of N-aryl-N-troponyl amides containing an electron-donating group on the phenyl ring. NMR spectral studies indicated that the E/Z conformational preferences of these amides can be reversibly controlled by pH-dependent protonation or deprotonation of the tropolone moiety. Thus, these compounds have potential applications as acid/base-controllable

  我们已经研究了苯环上含有一个供电子基团的N-芳基-N-肌钙蛋白酰胺的酸和碱诱导的构象变化。NMR光谱研究表明，这些酰胺的E / Z构象偏爱可通过托酚酮部分的pH依赖质子化或去质子化而可逆地控制。因此，这些化合物作为酸/碱可控的分子开关具有潜在的应用。
• Tropolone as a High-Performance Robust Anchoring Group for Dye-Sensitized Solar Cells
  作者：Tomohiro Higashino、Yamato Fujimori、Kenichi Sugiura、Yukihiro Tsuji、Seigo Ito、Hiroshi Imahori

  DOI：10.1002/anie.201502951

  日期：2015.7.27

  A tropolone group has been employed for the first time as an anchoring group for dye‐sensitized solar cells (DSSCs). The DSSC based on a porphyrin, YD2‐o‐C8T, with a tropolone moiety exhibited a power‐conversion efficiency of 7.7 %, which is only slightly lower than that observed for a reference porphyrin, YD2‐o‐C8, with a conventional carboxylic group. More importantly, YD2‐o‐C8T was found to be superior

  托酚酮基团首次被用作染料敏化太阳能电池（DSSC）的锚定基团。基于具有卟啉部分的卟啉YD2-o-C8T的DSSC的功率转换效率为7.7％，仅略低于使用常规羧酸的参比卟啉YD2-o-C8所观察到的功率转换效率团体。更重要的是，YD2邻C8T被认为是优于YD2邻C8相对于DSSC耐久性和结合能力的TiO 2。这些结果清楚地表明，就设备耐用性和光伏性能而言，托洛酮是DSSC极有希望的染料固定基团。
• EP1357104
  申请人：——

  公开号：——

  公开（公告）日：——
• US4258188A
  申请人：——

  公开号：US4258188A

  公开（公告）日：1981-03-24