| 1607027-31-5

• 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
• CAS: 1607027-31-5
• 化学式: C₂₃H₁₇ClN₂O₂
• 分子量: 388.853
• InChiKey: MJDDVFCDTZWVBG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  28.0
• 可旋转键数：
  3.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  56.33
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  2,3-二甲基吲哚 、 在 S-联萘酚磷酸酯 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 12.0h， 以94%的产率得到1′-(3-chlorobenzyl)-2″,3″-dimethyl-1H,1″H-[3,3′:3′,6″-terindol]-2′(1′H)-one
  参考文献：
  名称：

  Organocatalytic Arylation of 3-Indolylmethanols via Chemo- and Regiospecific C6-Functionalization of Indoles

  摘要：

  An organocatalytic arylation of 3-indolylmethanols has been established via chemo- and regiospecific C6-functionalization of 2,3-disubstituted indoles, leading to the production of bisindolyloxindoles containing an all-carbon quaternary stereocenter in high yields (up to 99% yield). This reaction not only represents the first catalytic arylation of 3-indolylmethanols using 2,3-disubstituted indoles as aromatic nucleophiles but also serves as a good example of direct catalytic C6-functionalization of indoles, which have been scarcely investigated. Besides, this approach also provides an efficient method to access a biologically important 3,3'-disubstituted oxindole framework and a 3',6-linked bisindole skeleton. Furthermore, the investigation of the activation mode suggested that the dual activation of an ion pair and H-bond between the substrates and the catalyst cooperatively contributed to the success of the reaction.

  DOI：

  10.1021/jo501989x

文献信息

• Organocatalytic enantioselective and (Z)-selective allylation of 3-indolylmethanol via hydrogen-bond activation
  作者：Yan Liu、Hong-Hao Zhang、Yu-Chen Zhang、Yan Jiang、Feng Shi、Shu-Jiang Tu

  DOI：10.1039/c4cc02056a

  日期：——

  asymmetric allylation of 3-indolylmethanol has been established via hydrogen-bond activating mode, which directly assembles isatin-derived 3-indolylmethanols and o-hydroxystyrenes into chiral allyl-substituted oxindoles with one all-carbon quaternary stereogenic center and one newly formed C=C bond in excellent enantioselectivity and (Z)-selectivity (up to 97% ee, >20 : 1 Z/E ratio). This transformation provides

  已通过氢键活化模式建立了3-吲哚甲醇的有机催化不对称烯丙基化反应，该方法直接将由靛红衍生的3-吲哚甲醇和邻羟基苯乙烯组装成具有一个全碳季立体中心和一个新形成的C的手性烯丙基取代的羟吲哚。 = C键具有出色的对映选择性和（Z）选择性（高达97％ee，> 20：1 Z / E比）。这种转化为吲哚的不对称C3官能化和3-吲哚基甲醇的烯丙基化提供了一个有效的策略，并且可以精确控制CC和C = C键形成中的立体选择性。
• Catalyst-Controlled Chemoselective Reaction of 3-Indolylmethanols with Cyclic Enaminones Leading to C2-Functionalized Indoles
  作者：Xin Li、Wei Tan、Yu-Xin Gong、Feng Shi

  DOI：10.1021/jo502782b

  日期：2015.2.6

  A catalyst-controlled chemoselective formal 1,2-addition of 3-indolylmethanols with cyclic enaminones has been established in the presence of TfOH as a strong acid, which afforded C2-functionalized indole derivatives in generally good yields (up to 89% yield). This reaction not only confronted the great challenge in 1,2-addition of 3-indolylmethanols but also provided a good strategy for C2-functionalization

  在作为强酸的TfOH存在下，已建立了由催化剂控制的3-吲哚甲醇与环烯胺酮的化学选择形式1,2-加成反应，该反应以通常良好的收率（最高89％的收率）提供了C2官能化的吲哚衍生物。该反应不仅面临3-吲哚基甲醇在1，2-加成中的巨大挑战，而且为吲哚衍生物的C 2-官能化提供了良好的策略。对反应机理的研究表明，该正式的1,2-加成包括1,4-加成/ [1,3] -C迁移/异构化的串联序列，其中， 1,4-加成产物是关键步骤，催化剂的酸度在观察到的化学选择性中起着决定性的作用。
• Catalytic Asymmetric Formal [3+3] Cycloaddition of an Azomethine Ylide with 3-Indolylmethanol: Enantioselective Construction of a Six-Membered Piperidine Framework
  作者：Feng Shi、Ren-Yi Zhu、Wei Dai、Cong-Shuai Wang、Shu-Jiang Tu

  DOI：10.1002/chem.201304187

  日期：2014.2.24

  catalytic asymmetric formal [3+3] cycloaddition of 3‐indolylmethanol and an in situ‐generated azomethine ylide has been established to construct a chiral six‐membered piperidine framework with two stereogenic centers. This approach not only represents the first enantioselective cycloaddition of isatin‐derived 3‐indolylmethanol, but also has realized an unusual enantioselective formal [3+3] cycloaddition

  已经建立了3-吲哚基甲醇的催化不对称形式[3 + 3]环加成反应和原位生成的甲亚胺叶立德，以构建具有两个立体中心的手性六元哌啶骨架。这种方法不仅代表了由靛红衍生的3-二吲哚甲醇的首次对映选择性环加成，而且实现了偶氮甲内酯的不寻常的对映选择性形式[3 + 3]环加成，而不是其常见的[3 + 2]环加成。此外，该方案结合了多组分反应和有机催化的优点，可以高效地将各种由靛红衍生的3-吲哚基甲醇，醛和氨基酯组装成结构上不同的螺[吲哚啉-3,4'-吡啶并吲哚]，碳四元立体异构中心，具有高收率和出色的对映选择性（高达93％的收率，>ee））。尽管反应的非对映选择性通常是中等的，但大多数非对映异构体可通过使用柱色谱，然后进行制备性TLC分离。
• Catalytic Asymmetric Aza-ene Reaction of 3-Indolylmethanols with Cyclic Enaminones: Enantioselective Approach to C3-Functionalized Indoles
  作者：Wei Tan、Bai-Xiang Du、Xin Li、Xu Zhu、Feng Shi、Shu-Jiang Tu

  DOI：10.1021/jo500644v

  日期：2014.5.16

  The catalytic asymmetric aza-ene reactions of 3-indolylmethanols with cyclic enaminones and the highly enantioselective aza-ene reactions utilizing cyclic aza-ene components have been established, which directly assemble isatin-derived 3-indolylmethanols and dimedone-derived enaminones into C3-functionalized chiral indoles with one all-carbon quaternary stereogenic center in high yields and excellent enantioselectivities (up to 99% yield, up to 95:5 er).