N-(benzenesulfonyl)-3-ethoxy-1-<(methoxymethyl)oxy>-2-methylcarbazole | 176327-49-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: N-(benzenesulfonyl)-3-ethoxy-1-<(methoxymethyl)oxy>-2-methylcarbazole
• 英文别名: 9-(Benzenesulfonyl)-3-ethoxy-1-(methoxymethoxy)-2-methylcarbazole
• CAS: 176327-49-4
• 化学式: C₂₃H₂₃NO₅S
• 分子量: 425.505
• InChiKey: KNHCZNYUUQFULE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  30
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  75.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-(benzenesulfonyl)-3-ethoxy-1-<(methoxymethyl)oxy>-2-methylcarbazole 在 吡啶 、 sodium hydroxide 、 四(三苯基膦)钯 、 三甲基氯硅烷 、 三溴化硼 、 sodium iodide 作用下， 生成 2-methyl-1-phenyl-9H-carbazol-3-ol
  参考文献：
  名称：

  丙二烯介导的电环反应全合成咔唑他汀和乙酰唑

  摘要：

  自由基清除剂carazostatin和海洋生物碱hyellazole是通过一种新型的由丙二烯介导的涉及吲哚2,3-键的电环反应合成的，这是关键步骤。

  DOI：

  10.1016/0040-4039(96)00378-4
• 作为产物：
  描述：

  1-(benzenesulfonyl)-3-(2-ethoxyethenyl)-2-[1-(methoxymethoxy)prop-2-ynyl]indole 在 potassium tert-butylate 作用下， 以 四氢呋喃 、 叔丁醇 为溶剂， 以43%的产率得到3-ethoxy-1-<(methoxymethyl)oxy>-2-methylcarbazole
  参考文献：
  名称：

  Antioxidant Effects of the Hydroxy Groups in the Simple Phenolic Carbazoles

  摘要：

  Antioxidant activities of the simple phenolic carbazoles 5-11 were evaluated by 2,2-diphenyl-1-picrylhydrazyl and 2,2'-azinobis-(3-ethylbenzthiazoline-6-sulfonate)(+) radical scavenging assays. The simple phenolic carbazoles 5-7, 9, and 11 exhibited stronger antioxidant activities than a-tocopherol, and similar antioxidant activities as phenolic carbazole alkaloids carazostatin (1), and carbazomadurins A (3) and B (4). Bond dissociation energies and highest occupied molecule orbital energy levels of a series of phenolic carbazoles including phenolic carbazole alkaloids were calculated. The reducing ability of the phenolic carbazole core could be important role for the antioxidant activity of carbazole alkaloids 1, 3, and 4.

  DOI：

  10.3987/com-15-13363

文献信息

• Total syntheses of carazostatin and hyellazole by allene-mediated electrocyclic reaction
  作者：Tominari Choshi、Takuya Sada、Hiroyuki Fujimoto、Chizu Nagayama、Eiichi Sugino、Satoshi Hibino

  DOI：10.1016/0040-4039(96)00378-4

  日期：1996.4

  The free radical scavenger carazostatin and the marine alkaloid hyellazole have been synthesized by a new type of allene-mediated electrocyclic reaction involving the indole 2,3-bond as a key step.

  自由基清除剂carazostatin和海洋生物碱hyellazole是通过一种新型的由丙二烯介导的涉及吲哚2,3-键的电环反应合成的，这是关键步骤。
• Total Syntheses of Carazostatin, Hyellazole, and Carbazoquinocins B−F
  作者：Tominari Choshi、Takuya Sada、Hiroyuki Fujimoto、Chizu Nagayama、Eiichi Sugino、Satoshi Hibino

  DOI：10.1021/jo962038t

  日期：1997.4.1

  Total syntheses of carazostatin (1), hyellazole (2a), and carbazoquinocins B-F (3b-f) have been completed. The cross-coupling reaction between 3-iodoindole 8 and vinylstannane 11b gave the 3-alkenylindole 7. Treatment of 7 with ethynylmagnesium bromide, followed by etherification of the resulting alcohol 12 with MOMCl, yielded the 3-alkenyl-2-propargylindole 6. The compound 6 was treated with t-BuOK

  Carazostatin（1），hyellazole（2a）和carbazoquinocins BF（3b-f）的总合成已完成。3-碘吲哚8和乙烯基锡烷11b之间的交叉偶联反应得到3-烯基吲哚7。用乙炔基溴化镁处理7，随后用MOMC1醚化所得醇12，得到3-烯基-2-炔丙基吲哚6。将化合物6在t-BuOH中在90℃下用t-BuOK处理，以通过烯丙基介导的电环反应与N-脱保护的咔唑13一起获得所需的咔唑4。衍生自4a或4c的咔唑13a经两步转化为三氟甲磺酸酯24。在钯催化剂的存在下，使三氟甲磺酸酯24与9-庚基-9-BBN或苯基硼酸进行Suzuki交叉偶联反应，以产生1-庚基咔唑25a和1-苯基咔唑25b。裂解25a的醚键产生了咔唑他汀（1）。切割25b的醚键，然后进行O-甲基化，得到乙酰唑（2a）。用苯硒酸酐氧化Carazostatin（1），得到咔唑喹啉C（3c）。以类似的方式，分别合成了咔唑喹啉B和DF（3b，df）。
• Antioxidant Effects of the Hydroxy Groups in the Simple Phenolic Carbazoles
  作者：Tominari Choshi、Haruto Fujioka、Yuhzo Hieda、Noriyuki Hatae、Makoto Anraku、Nobuyasu Matsuura、Kazuhide Uemura、Satoshi Hibino、Hisao Tomida、Osamu Hori

  DOI：10.3987/com-15-13363

  日期：——

  Antioxidant activities of the simple phenolic carbazoles 5-11 were evaluated by 2,2-diphenyl-1-picrylhydrazyl and 2,2'-azinobis-(3-ethylbenzthiazoline-6-sulfonate)(+) radical scavenging assays. The simple phenolic carbazoles 5-7, 9, and 11 exhibited stronger antioxidant activities than a-tocopherol, and similar antioxidant activities as phenolic carbazole alkaloids carazostatin (1), and carbazomadurins A (3) and B (4). Bond dissociation energies and highest occupied molecule orbital energy levels of a series of phenolic carbazoles including phenolic carbazole alkaloids were calculated. The reducing ability of the phenolic carbazole core could be important role for the antioxidant activity of carbazole alkaloids 1, 3, and 4.