tert-butyl 3-phenyl-1,2,3,4-tetrahydrocarbazole-9-carboxylate | 1179445-04-5

• 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: tert-butyl 3-phenyl-1,2,3,4-tetrahydrocarbazole-9-carboxylate
• 英文别名: tert-butyl 1,2,3,4-tetrahydro-3-phenyl-9H-carbazole-9-carboxylate
• CAS: 1179445-04-5
• 化学式: C₂₃H₂₅NO₂
• 分子量: 347.457
• InChiKey: XQDKOSOLPXVURR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  31.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  碘苯二乙酸 、 tert-butyl 3-phenyl-1,2,3,4-tetrahydrocarbazole-9-carboxylate 在 四丁基碘化铵 、 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以68%的产率得到tert-butyl 1-acetoxy-3-phenyl-1,2,3,4-tetrahydrocarbazole-9-carboxylate
  参考文献：
  名称：

  Iodine-Mediated α-Acetoxylation of 2,3-Disubstituted Indoles

  摘要：

  A new method for direct alpha-functionalization of 2,3-disubstituted indoles has been developed. The present reaction provides alpha-acetoxy indole derivatives regioselectively under mild conditions using commercially available and nontoxic iodine reagents. This reaction is a useful synthetic tool because obtained alpha-acetoxy products can be transformed into various functionalized indoles by substitution reactions with nucleophiles.

  DOI：

  10.1021/ol302983t
• 作为产物：
  描述：

  4-苯基环己酮 在 4-二甲氨基吡啶 、 硫酸 、 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 生成 tert-butyl 3-phenyl-1,2,3,4-tetrahydrocarbazole-9-carboxylate
  参考文献：
  名称：

  Iodine-Mediated α-Acetoxylation of 2,3-Disubstituted Indoles

  摘要：

  A new method for direct alpha-functionalization of 2,3-disubstituted indoles has been developed. The present reaction provides alpha-acetoxy indole derivatives regioselectively under mild conditions using commercially available and nontoxic iodine reagents. This reaction is a useful synthetic tool because obtained alpha-acetoxy products can be transformed into various functionalized indoles by substitution reactions with nucleophiles.

  DOI：

  10.1021/ol302983t

文献信息

• Generation of<i>N</i>-(<i>tert</i>-Butoxycarbonyl)indole-2,3-quinodimethane and Its [4+2]-Type Cycloaddition
  作者：Fuyuhiko Inagaki、Masaya Mizutani、Norikazu Kuroda、Chisato Mukai

  DOI：10.1021/jo901325d

  日期：2009.8.21

  The two conditions for the preparation of the reactive N-(tert-butoxycarbonyl)indolo-2,3-quinodimethane intermediate were developed by the reaction of the N-(tert-butoxycarbonyl)-2-(1-ethoxycarbonyloxymethylallenyl)aniline with K2CO3 or Pd2(dba)3 in refluxing toluene. The resulting N-(tert-butoxycarbonyl)indolo-2,3-quinodimethane was captured by several alkenyl and alkynyl dienophiles to provide the

  通过使N-（叔丁氧基羰基）-2-（1-乙氧基羰氧基甲基甲基烯基）苯胺与K 2反应，开发了制备反应性N-（叔丁氧基羰基）吲哚-2,3-喹二甲烷中间体的两个条件。回流甲苯中的CO 3或Pd 2（dba）3。所得的N-（叔丁氧基羰基）吲哚-2,3-喹二甲烷被数个烯基和炔基二亲二烯体捕获，以提供相应的四氢-和二氢咔唑衍生物。
• Iodine-Mediated α-Acetoxylation of 2,3-Disubstituted Indoles
  作者：Hisaaki Zaimoku、Takashi Hatta、Tsuyoshi Taniguchi、Hiroyuki Ishibashi

  DOI：10.1021/ol302983t

  日期：2012.12.7

  A new method for direct alpha-functionalization of 2,3-disubstituted indoles has been developed. The present reaction provides alpha-acetoxy indole derivatives regioselectively under mild conditions using commercially available and nontoxic iodine reagents. This reaction is a useful synthetic tool because obtained alpha-acetoxy products can be transformed into various functionalized indoles by substitution reactions with nucleophiles.