5-甲氧基-2-乙烯基-1H-吲哚 | 622863-63-2

• 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
• 中文名称: 5-甲氧基-2-乙烯基-1H-吲哚
• 英文名称: 5-methoxy-2-vinyl-1H-indole
• 英文别名: 2-ethenyl-5-methoxy-1H-indole
• CAS: 622863-63-2
• 化学式: C₁₁H₁₁NO
• 分子量: 173.214
• InChiKey: YCEHKOJSKAMBOS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  25
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  5-甲氧基-2-乙烯基-1H-吲哚 在 manganese(IV) oxide 作用下， 以 1,4-二氧六环 为溶剂， 反应 19.0h， 生成 9-methoxypyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione
  参考文献：
  名称：

  4-Phenylpyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione Inhibitors of the Checkpoint Kinase Wee1. Structure−Activity Relationships for Chromophore Modification and Phenyl Ring Substitution

  摘要：

  High-throughput screening has identified a novel class of inhibitors of the checkpoint kinase Wee1, which have potential for use in cancer chemotherapy. These inhibitors are based on a 4-phenylpyrrolo[3,4-c]carbazole- 1,3(2H,6H)-dione template and have been shown by X-ray crystallography to bind at the ATP site of the enzyme. An extensive study of the effects of substitution around this template has been carried out, which has identified substituents which lead to improvements in potency and selectivity for Wee1. While retention of the maleimide ring and pendant 4-phenyl group is necessary for potency, replacement of the carbazole nitrogen by oxygen is well tolerated and results in improved Wee1 selectivity against the related checkpoint kinase Chk1. Wee1 potency and selectivity are also enhanced by the incorporation of lipophilic functionality at the 2'-position of the 4-phenyl ring, and Wee1 selectivity against Chk1 is favored by C3-C5 alkyl substitution of the carbazole nitrogen. These studies provide a basis for the design of active analogues of the pyrrolocarbazole lead with improved physical properties.

  DOI：

  10.1021/jm0512591
• 作为产物：
  描述：

  5-甲氧基-2-硝基苯甲醛 在 tris(bipyridine)ruthenium(II) dichloride hexahydrate 、 铁粉 、 potassium carbonate 、 溶剂黄146 、 sodium nitrite 作用下， 以 乙醇 、 水 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 49.0h， 生成 5-甲氧基-2-乙烯基-1H-吲哚
  参考文献：
  名称：

  通过可见光诱导的苯乙烯叠氮化物的光催化环化反应合成2位取代的吲哚

  摘要：

  在室温下，在钌络合物Ru（bpy）3 Cl 2（0.5 mol％）作为光催化剂存在的情况下，已经开发了可见光诱导的苯乙烯叠氮化物的光催化分子内环化反应。当前的光催化策略具有操作简便以及对官能团的耐受性高的特点，并提供了以良好或优异的收率轻松获得各种2个取代的N无氮吲哚的方法。重要的是，本方法可以采用阳光作为光源以提供相应的产物而不会损失反应效率。

  DOI：

  10.1002/adsc.201400527

文献信息

• Non‐Bonding Electron Pair versus π‐Electrons in Solution Phase Halogen Bond Catalysis: Povarov Reaction of 2‐Vinylindoles and Imines
  作者：Takumi Suzuki、Satoru Kuwano、Takayoshi Arai

  DOI：10.1002/adsc.202000494

  日期：2020.8.4

  The non‐bonding electron pair (n‐pair) of heteroatoms and π‐electrons are both efficient halogen bond (XB) acceptors. In solid and gas phase studies, n‐pairs generally prevail over π‐bonding orbitals as XB acceptors, whereas few studies have been conducted regarding the preference in solution phase. Herein, the Povarov reaction via the C−I⋅⋅⋅N XB interaction and [4+2] cycloaddition via the C−I⋅⋅⋅π

  杂原子和π电子的非键电子对（n对）都是有效的卤素键（XB）受体。在固相和气相研究中，n对通常胜过π键轨道作为XB受体，而关于固溶相偏好的研究很少。在本文中，对通过C–I⋅⋅·N XB相互作用的Povarov反应和通过C–I⋅⋅⋅π XB相互作用的[4 + 2]环加成进行了评估，表明n对在XB催化中占主导地位。解决方案中的系统。XB供体催化的Povarov反应以良好的收率得到了多种吲哚基-四氢喹啉衍生物。还开发了吲哚基喹啉的合成方法。
• Synthesis, NMR conformational analysis and pharmacological evaluation of 7,7a,13,14-tetrahydro-6H-cyclobuta[b]pyrimido[1,2-a:3,4-a′]diindole analogues as melatonin receptor ligands
  作者：Mohamed I. Attia、Deniz Güclü、Barbara Hertlein、Justin Julius、Paula A. Witt-Enderby、Darius P. Zlotos

  DOI：10.1039/b705550a

  日期：——

  A structure for the self-condensation product of 2-(1H-indol-2-yl)ethyl tosylate2a, previously proposed as 6,7,14,15-tetrahydro-15aH-azocino[1,2-a:6,5-b]diindole3a, was revised based on the 13C-2D-INADEQUATE experiment, and proved to be 7,7a,13,14-tetrahydro-6H-cyclobuta[b]pyrimido[1,2-a:3,4-a′]diindole4a. A mechanism for the unexpected formation of this novel hexacyclic heterocycle was proposed and its NMR solution structure was elucidated. Five derivatives of the title ring skeleton 12–16 designed as melatonin receptor ligands were synthesized and their affinities for the human MT1 and MT2 receptors were determined. Both butyramides 13 and 15, as well as the non-methoxy acetamide 12 exhibited micromolar binding affinities for both receptors being slightly MT2 selective. The methoxy acetamide 14 showed the best pharmacological profile exhibiting a five times higher affinity for MT1 (Ki = 49 nM) than for MT2 (Ki = 246 nM) receptor.

  2-(1H-吲哚-2-基)乙基对甲苯磺酸酯自缩合产物的结构2a，之前被提议为6,7,14,15-四氢-15aH-偶氮环[1,2-a:6,5-b]二吲哚3a，基于13C-2D-INADEQUATE实验进行了修订，证明其为7,7a,13,14-四氢-6H-环丁[b]嘧啶[1,2-a:3,4-a']二吲哚4a。提出了一种机制来解释这个新颖六元环杂环的意外形成，并阐明了其NMR溶液结构。合成了五种设计为褪黑素受体配体的标题环骨架衍生物12–16，并测定其对人MT1和MT2受体的亲和力。布酸酰胺衍生物13和15，以及非甲氧基乙酰胺12对这两种受体都表现出微摩尔结合亲和力，稍微选择性偏向MT2。甲氧基乙酰胺14则展示了最佳的药理特征，对MT1（Ki = 49 nM）的亲和力比MT2（Ki = 246 nM）高出五倍。
• Catalysis Based on C−I⋅⋅⋅π Halogen Bonds: Electrophilic Activation of 2‐Alkenylindoles by Cationic Halogen‐Bond Donors for [4+2] Cycloadditions
  作者：Satoru Kuwano、Takumi Suzuki、Masahiro Yamanaka、Ryosuke Tsutsumi、Takayoshi Arai

  DOI：10.1002/anie.201904689

  日期：2019.7.22

  Homo‐ and cross‐[4+2] cycloadditions of 2‐alkenylindoles, catalyzed by cationic halogen‐bond donors, were developed. Under mild reaction conditions, 3‐indolyl‐substituted tetrahydrocarbazole derivatives were obtained in good to excellent yields. Experimental and quantum calculation studies revealed that the electrophilic activation of 2‐alkenylindoles was achieved by C−I⋅⋅⋅π halogen bonds.

  开发了由阳离子卤素键供体催化的2-烯基吲哚的均和环[4 + 2]环加成反应。在温和的反应条件下，可以很好地获得3-吲哚基取代的四咔唑衍生物。实验和量子计算研究表明，2-烯基吲哚的亲电活化是通过C−I⋅⋅⋅π卤素键实现的。
• Convenient Synthesis of Tetrahydro-γ-carbolines and Tetrahydroquinolines through a Chemo- and Regioselectivity Switch by a Brønsted Acid Catalyzed, One-Pot, Multicomponent Reaction
  作者：Hong-Gang Cheng、Cai-Bao Chen、Fen Tan、Ning-Jie Chang、Jia-Rong Chen、Wen-Jing Xiao

  DOI：10.1002/ejoc.201000853

  日期：2010.9

  An efficient, one-pot, multicomponent reaction of aldehydes 1, p-methoxyaniline (2a), and 2-vinylindoles 3 was developed. This approach provides a practical approach to synthetically and biologically significant tetrahydro-γ-carboline and tetrahydroquinoline derivatives in good yields through a chemo- and regioselectivity switch, which can be tuned by simply changing the substituent on the indole component

  开发了醛 1、对甲氧基苯胺 (2a) 和 2-乙烯基吲哚 3 的高效、一锅多组分反应。这种方法提供了一种实用的方法来合成和生物学上重要的四氢-γ-咔啉和四氢喹啉衍生物，通过化学和区域选择性开关，可以通过在相同的反应条件下简单地改变吲哚组分上的取代基来调整。
• A Hypervalent Cyclic Dibenzoiodolium Salt as a Halogen‐Bond‐Donor Catalyst for the [4+2] Cycloaddition of 2‐Alkenylindoles
  作者：Yuki Nishida、Takumi Suzuki、Yuri Takagi、Emi Amma、Ryoya Tajima、Satoru Kuwano、Takayoshi Arai

  DOI：10.1002/cplu.202100089

  日期：2021.5

  A stable, hypervalent cyclic dibenzoiodolium salt acted as a strong halogen bonding (XB)‐donor catalyst for [4+2] cycloaddition of 2‐alkenylindoles, and not as an oxidizing agent. The cross‐[4+2] cycloaddition of 2‐vinylindoles with 2‐alkenylindoles was catalyzed smoothly by the hypervalent cyclic dibenzoiodolium triflate catalyst to give the tetrahydrocarbazoles in up to 99 % yield with 17 : 1 diastereoselectivity

  一种稳定的高价环状二苯并碘鎓盐充当 2-烯基吲哚 [4+2] 环加成的强卤素键 (XB) 供体催化剂，而不是氧化剂。高价环状二苯并碘鎓三氟甲磺酸盐催化剂顺利催化2-乙烯基吲哚与2-烯基吲哚的交叉[4+2]环加成反应，得到四氢咔唑，收率高达99%，非对映选择性为17:1。高价环状二苯并碘鎓盐也适用于 2-乙烯基吲哚与N-对-甲氧基苯基 (PMP) 亚胺的 Povarov 反应，生成吲哚基四氢喹啉，产率 83%。