5-isopropyl-2-tosyloxytropone | 69141-45-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5-isopropyl-2-tosyloxytropone
• 英文别名: 5-isopropyl-2-(toluene-4-sulfonyloxy)-cycloheptatrienone；5-Isopropyl-2-(toluol-4-sulfonyloxy)-cycloheptatrienon；(7-Oxo-4-propan-2-ylcyclohepta-1,3,5-trien-1-yl) 4-methylbenzenesulfonate
• CAS: 69141-45-3
• 化学式: C₁₇H₁₈O₄S
• 分子量: 318.394
• InChiKey: ZCZQFLHTEOBZDN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  68.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-isopropyl-2-tosyloxytropone 在 氨 作用下， 生成 2-氨基-4-异丙基-2,4,6-环庚三烯-1-酮
  参考文献：
  名称：

  Sato, Nippon Kagaku Zasshi, 1959, vol. 80, p. 1056

  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-tosyloxytropone
  参考文献：
  名称：

  SUDZUKI, KATSUMI;XIVATA, OSAMU;NAKAMURA, TORU;YASUNAMI, MASABUMI;TAKASEH,+

  摘要：

  DOI：

文献信息

• Synthesis and anti-ulcer activities of sodium alkylazulene sulfonates.
  作者：TAKASHI YANAGISAWA、SHUICHI WAKABAYASHI、TSUYOSHI TOMIYAMA、MASAFUMI YASUNAMI、KAHEI TAKASE

  DOI：10.1248/cpb.36.641

  日期：——

  Many derivatives of sodium alkylazulene sulfonates were newly synthesized and their antiulcer activites were examined in Shay pylorus-ligated rats. The values of lipophilicity (log P), a physicochemical parameter, of these new azulene derivatives were also examined in order to study the structure-activity relationship. The optimum value of log P which gave maximum anti-ulcer activity was about -1.0. Among the derivatives of azulene examined, 3-ethyl-7-isopropylazulene-1-sulfonic acid sodium salt (KT1-32) exhibited an extremely potent inhibitory action against Shay ulcer, and its antipeptic activity was more potent than than of guaiazulene sodium sulfonate (GAS). Furthermore, KT1-32 was extremely stable on heating as compared to GAS.

  多种新合成的钠代烷基吖啶磺酸盐衍生物在沙伊幽门结扎大鼠中进行了其抗溃疡活性的检测。此外，还研究了这些新吖啶衍生物的亲脂性（log P）这一物理化学参数，以探讨结构-活性关系。log P的最佳值，即提供最大抗溃疡活性的值，大约为-1.0。在检测的吖啶衍生物中，3-乙基-7-异丙基吖啶-1-磺酸钠盐（KT1-32）对沙伊溃疡显示出极其强大的抑制作用，其抗胃酸活性比愈创木基吖啶磺酸钠（GAS）更强。此外，与GAS相比，KT1-32在加热过程中极为稳定。
• Synthesis and Analysis of Positive Inotropic Effects of 3-Substituted-2H-cyclohepta(b)furan-2-one Derivatives.
  作者：Masayuki YOKOTA、Takashi YANAGISAWA、Kazuhiro KOSAKAI、Shuichi WAKABAYASHI、Tsuyoshi TOMIYAMA、Masafumi YASUNAMI

  DOI：10.1248/cpb.42.865

  日期：——

  Several 3-substituted-2H-cyclohepta[b]furan-2-one derivatives were prepared and tested in vitro for positive inotropic character. Introduction of an isopropyl group at the 5-position of compound 8a caused an increase of PIC50 (negative logarithm of the dosage which increases the contractile force by 50%) from 4.48 to 5.10. Among the 5-isopropyl-8-alkoxy compounds, the isopropoxy compound 12f had the most potent activity with a PIC50 value of 5.99. Conversion of the ester group at the 3-position to a methylene group and of the alkoxy group at the 8-position to a substituted amino group caused a decrease in activity. The most active compound, 12f, was also found to have a weaker heart rate (HR)-increasing effect compared to milrinone and amrinone.

  合成了几种3-取代的-2H-环庚[b]呋喃-2-酮衍生物，并在体外测试了它们的正性肌力特性。在化合物8a的5-位引入异丙基，使得PIC50值（增加收缩力50%的剂量的负对数）从4.48增加到5.10。在5-异丙基-8-烷氧基化合物中，异丙氧基化合物12f具有最强的活性，PIC50值为5.99。将3-位的酯基转换为亚甲基，将8-位的烷氧基转换为取代氨基，会导致活性降低。最活跃的化合物12f，与米力农和氨力农相比，对心率（HR）增加的影响较弱。
• A Convenient Synthesis of 5-Aryltropolones via Novel Benzidine Type Rearrangement of 2-(2-Arylhydrazino)tropones
  作者：Tetsuo Nozoe、Kahei Takase、Hiroaki Saito、Hiroshi Yamamoto、Kimiaki Imafuku

  DOI：10.1246/cl.1986.1577

  日期：1986.9.5

  Treatment of a wide variety of 2-(2-arylhydrazino)tropones with ethanolic acid at 50–80 °C readily gave the benzidine type rearrangement products, i.e. 2-amino-5-(4-aminoaryl)tropones, which in turn were conveniently led to the corresponding 5-aryltropolones that can be utilized for synthesizing B-ring-open analogues of colchicine.

  在 50–80 °C 下用乙醇酸处理各种 2-(2-芳基肼基) 托酮很容易得到联苯胺型重排产物，即 2-氨基-5-(4-氨基芳基)托酮，这反过来又很方便导致相应的 5-芳基托酚酮可用于合成秋水仙碱的 B 环开环类似物。
• Synthesis and Reactions of 2-Arylhydrazinotropones. I. Preparation of 2-(2-Arylhydrazino)tropones and the 4-Substituted Derivatives
  作者：Tetsuo Nozoe、Kimiaki Imafuku、Bing-Zhu Yin、Masaaki Honda、Yasutomo Goto、Yasushi Hara、Takayoshi Andoh、Hiroshi Yamamoto

  DOI：10.1246/bcsj.61.2531

  日期：1988.7

  group at the 5-position, 4-substituted 2-(2-arylhydrazino)tropones were obtained as the major products by the abnormal substitution reaction. These 2-(2-arylhydrazino)tropones are expected to effectively serve as precursors for a convenient synthesis of 5-aryl-substituted tropolones via benzidine-type rearrangement. 1H NMR (200 or 500-MHz) parameters for these 4-substituted 2-(2-arylhydrazino)tropones

  通过 2-甲苯磺酰氧托酮与芳基肼反应制备了多种 2-(2-芳基肼基) 托酮。二聚化合物 6,6'-双(芳基肼基)-1,1'-双(2,4-环庚二烯)-7,7'-二酮、2-苯胺托酮和 3-(2-芳基肼基)托酮被分离为在某些情况下是次要产品。类似地，以 2-tosyloxytropones 开始，在 5-位带有异丙基、异丙烯基、（1-乙酰氨基乙基）和受保护的乙酰基，通过异常取代获得 4-取代的 2-（2-芳基肼基）tropones 作为主要产物反应。预计这些 2-(2-芳基肼基) 托酚酮可有效地用作通过联苯胺型重排方便合成 5-芳基取代的托酚酮的前体。
• Reactive Troponoids and<i>o</i>-Aminophenol. II. The Formation of Cyclohepta[<i>b</i>][1,4]benzoxazine and 11<i>H</i>-Cyclohepta[<i>b</i>][1,4]benzoxazin-10-one Derivatives from Isomeric Isopropyl-2-chlorotropones
  作者：Tetsuo Nozoe、Taichi Someya

  DOI：10.1246/bcsj.51.3316

  日期：1978.11

  The reactions of three isomeric isopropyl-2-chlorotropones with o-aminophenol were investigated. 8-Isopropylcyclohepta[b][1,4]benzoxazine was obtained from 5-isopropyl-2-chlorotropone, while 4- and 6-isopropylderivatives gave the same mixture of 7- and 9-isopropylcyclohepta[b][1,4]benzoxazine. These facts showed that the amino group of o-aminophenol attacked both the C-1 and C-2 positions of 2-chlorotropones. Also 6-, 7-, and 8-isopropyl-11H-cyclohepta[b][1,4]benzoxazin-10-ones were obtained as the minor products of these reactions.

  对三种异构体异丙基-2-氯托烯的反应与邻氨基酚进行了研究。5-异丙基-2-氯托烯得到了8-异丙基环七[b][1,4]苯噁嗪，而4-和6-异丙基衍生物则生成了相同的7-和9-异丙基环七[b][1,4]苯噁嗪混合物。这些事实表明邻氨基酚的氨基攻击了2-氯托烯的C-1和C-2位。同时，6-、7-和8-异丙基-11H-环七[b][1,4]苯噁嗪-10-酮也作为这些反应的次要产物得到了。

表征谱图