10-benzyl-8,9-dihydropyrido[1,2-a]indol-6(7H)-one | 98883-35-3

• 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: 10-benzyl-8,9-dihydropyrido[1,2-a]indol-6(7H)-one
• 英文别名: 10-benzyl-8,9-dihydro-7H-pyrido[1,2-a]indol-6-one；10-benzyl-8,9-dihydro-7H-pyrido[1,2-a]indol-6-one
• CAS: 98883-35-3
• 化学式: C₁₉H₁₇NO
• 分子量: 275.35
• InChiKey: JVTIINGAICJQGA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  22
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  10-benzyl-8,9-dihydropyrido[1,2-a]indol-6(7H)-one 、 碘苯二乙酸 在 四丁基碘化铵 、 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以89%的产率得到10-benzyl-6-oxo-6,7,8,9-tetrahydropyrido[1,2-a]indol-9-yl acetate
  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：

  2-benzyl-3-((2-iodophenyl)amino)cyclohex-2-en-1-one 在 potassium phosphate 、 palladium diacetate 作用下， 以 二甲基亚砜 为溶剂， 反应 0.17h， 以90%的产率得到10-benzyl-8,9-dihydropyrido[1,2-a]indol-6(7H)-one
  参考文献：
  名称：

  无配位钯催化环化/酰基迁移反应合成N稠合的多环吲哚

  摘要：

  描述了通过钯催化的环化/酰基迁移级联反应的N-稠合多环吲哚的有效合成。该反应是无配体的，可扩展的，并提供了从容易获得的起始原料获得各种有用的吲哚支架的途径。支持性的机理研究表明，该反应可能通过分子内α-芳基化机制进行。该方案的合成效用通过克级反应证明，并且可以合成吲哚生物碱和HSP90抑制剂。

  DOI：

  10.1021/acs.orglett.8b04128

文献信息

• Palladium-Catalyzed Coupling of Vinylogous Amides with Aryl Halides:  Applications to the Synthesis of Heterocycles
  作者：Scott D. Edmondson、Anthony Mastracchio、Emma R. Parmee

  DOI：10.1021/ol000031z

  日期：2000.4.1

  of vinylogous amides with aryl bromides and chlorides. The scope of this reaction with respect to the aryl component is investigated. Additionally, a tandem reaction sequence in which the above coupling is followed by an intramolecular Heck reaction is presented. These reactions can be applied to high-yielding, one-pot syntheses of nitrogen-containing heterocycles.

  [式中：见正文]本文描述的是乙烯基催化剂与芳基溴化物和氯化物的钯催化偶联的第一个例子。研究了该反应相对于芳基组分的范围。另外，提出了串联反应序列，其中上述偶联之后是分子内Heck反应。这些反应可用于高产的一锅合成含氮杂环。
• Cu-Catalyzed Arylation/Acyl Migration Cascade Reaction of Enaminones: Access to N-Fused Polycyclic and 2,3-Disubstituted Indoles
  作者：Weishuang Li、Zhan Dong、Yan Zhang、Zhen Zeng、Muhammad Usman、Wen-Bo Liu

  DOI：10.1021/acs.joc.9b00866

  日期：2019.6.21

  polycyclic and 2,3-disubstituted indoles by copper-catalyzed direct annulation/acyl migration reaction of enaminones is reported. This strategy features cheap and low loading of the catalyst/ligand, readily available starting materials, and good functional group compatibilities. Notably, allyl-containing substrates are also tolerated, which allows the downstream derivatization toward indole alkaloids.

  据报道，铜催化的烯胺酮的直接环化/酰基迁移反应可有效合成N稠合的多环和2,3-二取代的吲哚。该策略的特征在于催化剂/配体的便宜和低负载，易于获得的起始材料以及良好的官能团相容性。值得注意的是，还可以耐受含烯丙基的底物，从而可以向下游衍生为吲哚生物碱。
• Divergent Coupling of 2-Carbonyl-anilines and Diazo-cyclopentanones: Asymmetric Total Synthesis of (+)-Leucomidine A
  作者：Xiaotong Yao、Xiaosong Shan、Liansuo Zu

  DOI：10.1021/acs.orglett.8b02823

  日期：2018.10.19

  The direct coupling of 2-carbonyl-anilines and diazo-cyclopentanones, promoted by a rhodium catalyst and diphenyl phosphate, is reported for the divergent generation of both carbazolones and indolones. The strategy allows for the successful transfer of the substituents/functionality and the chirality of the coupling partners into the functionalized heterocyclic products, thus serving as the strategic

  据报道，铑催化剂和磷酸二苯酯促进了2-羰基苯胺和重氮-环戊酮的直接偶联，从而产生了咔唑酮和吲哚酮。该策略可以将取代基/官能团和偶联伙伴的手性成功转移到官能化的杂环产物中，从而可以作为天然产物合成的战略基础，如（+）-隐香氨酸A的简明不对称全合成所证明的那样。 。
• Synthesis of <i>N</i>-Fused Polycyclic Indoles via Ligand-Free Palladium-Catalyzed Annulation/Acyl Migration Reaction
  作者：Zhan Dong、Xiao-Wen Zhang、Weishuang Li、Zi-Meng Li、Wen-Yan Wang、Yan Zhang、Wei Liu、Wen-Bo Liu

  DOI：10.1021/acs.orglett.8b04128

  日期：2019.2.15

  An efficient synthesis of N-fused polycyclic indoles by a palladium-catalyzed annulation/acyl migration cascade reaction is described. The reaction is ligand-free, scalable, and provides access to a diverse range of useful indole scaffolds from readily available starting materials. Supporting mechanistic studies indicate that the reaction likely proceeds via an intramolecular α-arylation mechanism

  描述了通过钯催化的环化/酰基迁移级联反应的N-稠合多环吲哚的有效合成。该反应是无配体的，可扩展的，并提供了从容易获得的起始原料获得各种有用的吲哚支架的途径。支持性的机理研究表明，该反应可能通过分子内α-芳基化机制进行。该方案的合成效用通过克级反应证明，并且可以合成吲哚生物碱和HSP90抑制剂。
• 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.