4-(1,2-二甲基吲哚-3-基)丁烷-2-酮 | 61936-74-1

• 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: 4-(1,2-二甲基吲哚-3-基)丁烷-2-酮
• 英文名称: 4-(1,2-dimethylindol-3-yl)butan-2-one
• 英文别名: 4-<3'-(1,2-dimethylindolyl)>butan-2-one；4-(1,2-dimethyl-1H-indol-3-yl)butan-2-one；2-Butanone, 4-(1,2-dimethyl-1H-indol-3-yl)-
• CAS: 61936-74-1
• 化学式: C₁₄H₁₇NO
• 分子量: 215.295
• InChiKey: ZEISIUHQYOXYTM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  22
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  2-烯丙基-N-甲基苯胺 、 丁烯酮 在 双(乙腈)氯化钯(II) 、 碘 、 sodium carbonate 、 lithium chloride 作用下， 生成 4-(1,2-二甲基吲哚-3-基)丁烷-2-酮
  参考文献：
  名称：

  Palladium-assisted cyclization-insertion reactions. Synthesis of functionalized heterocycles

  摘要：

  DOI：

  10.1021/ja00530a044

文献信息

• B(C₆F₅)₃-Catalyzed Michael Reactions: Aromatic C–H as Nucleophiles
  作者：Wu Li、Thomas Werner

  DOI：10.1021/acs.orglett.7b00720

  日期：2017.5.19

  The Michael reaction is a widely used reaction for the C–C coupling of electron-poor olefins and C(sp3)–H pronucleophiles. Herein we report the Michael reaction between alkenes and aromatic as well as heteroaromatic compounds as aromatic C(sp2)–H nucleophiles under mild conditions. The reaction is catalyzed by readily available Lewis acidic B(C6F5)3 and proceeds with high regioselectivity for a wide

  迈克尔反应是贫电子烯烃与C（sp 3）-H前亲核试剂的C-C偶联反应中广泛使用的反应。在这里，我们报道了在温和条件下烯烃与芳香族以及杂芳香族化合物（如芳香族C（sp 2）–H亲核体）之间的迈克尔反应。该反应被易得的路易斯酸性B（C 6 F 5）3催化，并在较大的底物范围内以高区域选择性进行。
• Triflic Acid–Catalyzed Michael Reactions of Indole and Pyrrole Compounds with α,β‐Unsaturated Ketones in Water
  作者：Hai‐Bo Zhang、Li Liu、Yu‐Liang Liu、Yong‐Jun Chen、Jun Wang、Dong Wang

  DOI：10.1080/00397910601031504

  日期：2007.2.1

  Abstract The Michael reactions of indole and pyrrole compounds to α,β‐unsaturated ketones catalyzed by triflic acid (HOTf, 0.1–1 mol%) were performed in water to give alkylated indoles (3a–m) and dialkylsubstituted pyrroles (6a–b) in good to excellent yields.

  摘要 在三氟甲磺酸 (HOTf, 0.1–1 mol%) 的催化下，吲哚和吡咯化合物与 α,β-不饱和酮的迈克尔反应在水中进行，得到烷基化吲哚 (3a-m) 和二烷基取代的吡咯 (6a-b)良好的产量。
• Platinum-Catalyzed Multi-Step Reaction of Propargyl Alcohols with<i>N</i>-Heteroaromatics
  作者：Sivakolundu Bhuvaneswari、Masilamani Jeganmohan、Chien-Hong Cheng

  DOI：10.1002/asia.200900318

  日期：2010.1.4

  AbstractN‐Methyl indole reacts with but‐2‐yn‐1‐ol in the presence of PtCl2 in MeOH giving indole derivatives having a substituted 3‐oxobutyl group at the 3‐position in good yield. Under the reaction conditions, various substituted indoles and substituted propargyl alcohols are successfully involved in the reaction giving the corresponding addition products in good to moderate yields. The catalytic reaction can be further extended to N‐phenyl pyrrole. In the present multi‐step reaction, PtCl2 likely plays dual roles: as the catalyst for the rearrangement of propargyl alcohols to the corresponding alkenyl ketones and as the catalyst for the addition of indoles to the alkenyl ketones. Experimental evidence is provided to support the proposed mechanism.
• HEGEDUS L. S.; ALLEN G. F.; OLSEN D. J., J. AMER. CHEM. SOC., 1980, 102, NO 10, 3583-3587
  作者：HEGEDUS L. S.、 ALLEN G. F.、 OLSEN D. J.

  DOI：——

  日期：——
• Palladium-assisted cyclization-insertion reactions. Synthesis of functionalized heterocycles
  作者：Louis S. Hegedus、G. F. Allen、D. J. Olsen

  DOI：10.1021/ja00530a044

  日期：1980.5

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