3-iodo-1, 2-dimethyl-1H-indole | 37117-31-0

• 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: 3-iodo-1, 2-dimethyl-1H-indole
• 英文别名: 1,2-Dimethyl-3-iodoindole；3-iodo-1,2-dimethylindole
• CAS: 37117-31-0
• 化学式: C₁₀H₁₀IN
• 分子量: 271.101
• InChiKey: SSZIXUUGWDPQGJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  4.9
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  3-iodo-1, 2-dimethyl-1H-indole 、 在 四(三苯基膦)钯 作用下， 以 四氢呋喃 为溶剂， 反应 1.5h， 以45%的产率得到
  参考文献：
  名称：

  Palladium-Catalyzed Reactions of [Et₃NH]⁺ Salts of [(μ-RS)(μ-CO)Fe₂(CO)₆]⁻ Anions with Iodo-Aromatic Compounds To Give the Corresponding Butterfly μ-Acyl Fe/S Cluster Complexes

  摘要：

  Interestingly, the intermediate salts A [Et3NH] (A = (mu-RS)(mu-CO)Fe-2(CO)(6); R = i-Pr, sec-Bu, cy-C6H11, p-MeC6H4) prepared from Fe-3(CO)(12), RSH, and Et3N were found to react in situ with iodobenzene or its substituted derivatives in the presence of the catalyst precursor Pd(PPh3)(4) to give the benzoyl type mu-acyl complexes (mu-RS)(mu-ArCO)Fe-2(CO)(6) (Ar = phenyl or substituted phenyl), whereas the in situ reactions of A [Et3NH] with iodo-substituted aromatic heterocycles under the same conditions afforded the corresponding heterocyclic type mu-acyl complexes (mu-RS)(mu-ArCO)Fe-2(CO)(6) (Ar = heterocyclic or benzoheterocyclic group). Particularly worth noting is that such Pd-catalyzed C-C bond cross-coupling reactions are the first examples of catalytic reactions regarding A [Et3NH] salts reported so far. In addition, all the prepared new mu-acyl complexes and the three new intermediate salts A [Et3NH] (R = i-Pr, sec-Bu, cy-C6H11) were isolated and structurally characterized, while a possible pathway for such type Pd-catalyzed reactions regarding A [Et3NH] salts is suggested.

  DOI：

  10.1021/acs.organomet.5b00228
• 作为产物：
  描述：

  1,2-二甲基吲哚 在 碳酸氢钠 、 Selectfluor 、 potassium iodide 作用下， 以 甲苯 为溶剂， 反应 2.0h， 以67%的产率得到3-iodo-1, 2-dimethyl-1H-indole
  参考文献：
  名称：

  吲哚的直接C–H卤化

  摘要：

  已经开发出新颖，有效的无吲哚衍生物的无过渡金属C–H键卤化的化合物。通过此方案可以高度区域选择性地生成3-卤代（3-Br，3-I）吲哚。使用简单易得的卤化物盐（TBAB，KI）作为卤素源。无过渡金属和温和的条件使该协议非常易于操作和实用。

  DOI：

  10.1016/j.tetlet.2014.02.071

文献信息

• The direct C–H halogenations of indoles
  作者：Leilei Shi、Dongmei Zhang、Riyuan Lin、Chun Zhang、Xun Li、Ning Jiao

  DOI：10.1016/j.tetlet.2014.02.071

  日期：2014.4

  A novel and efficient transition metal-free C–H bond halogenation of indole derivatives has been developed. 3-Halogenated (3-Br, 3-I) indoles are highly regioselectively produced by this protocol. Simple and readily available halide salts (TBAB, KI) are employed as the halogen source. The transition metal-free and the mild conditions make this protocol very easy to handle and practical.

  已经开发出新颖，有效的无吲哚衍生物的无过渡金属C–H键卤化的化合物。通过此方案可以高度区域选择性地生成3-卤代（3-Br，3-I）吲哚。使用简单易得的卤化物盐（TBAB，KI）作为卤素源。无过渡金属和温和的条件使该协议非常易于操作和实用。
• US5294522A
  申请人：——

  公开号：US5294522A

  公开（公告）日：1994-03-15
• A Versatile C-H Halogenation Strategy for Indole Derivatives under Electrochemical Catalyst- and Oxidant-Free Conditions
  作者：Linhao Sun、Xing Zhang、Zilong Li、Jimei Ma、Zhen Zeng、Hong Jiang

  DOI：10.1002/ejoc.201800267

  日期：2018.9.23

  An economical and scalable electrochemical protocol for regioselective 3C–H halogenation of indole derivatives is reported. This strategy provides access to a host of 3‐iodo‐, 3‐bromo‐, 3‐chloro‐, and 3‐thiocyanoindole derivatives under mild conditions using inexpensive (pseudo)halide salts as the sole reagent. No supplementary electrolyte salt is necessary.

  据报道，一种经济且可扩展的电化学方案可用于吲哚衍生物的区域选择性3C–H卤化。该策略可在温和条件下使用廉价的（伪）卤化物盐作为唯一试剂，获得大量3-碘，3-溴，3-氯和3-硫氰基吲哚衍生物。无需补充电解质盐。
• Palladium-Catalyzed Reactions of [Et₃NH]⁺ Salts of [(μ-RS)(μ-CO)Fe₂(CO)₆]⁻ Anions with Iodo-Aromatic Compounds To Give the Corresponding Butterfly μ-Acyl Fe/S Cluster Complexes
  作者：Li-Cheng Song、Hao Tan、An-Guo Zhu、Yuan-Yuan Hu、Hao Chen

  DOI：10.1021/acs.organomet.5b00228

  日期：2015.5.11

  Interestingly, the intermediate salts A [Et3NH] (A = (mu-RS)(mu-CO)Fe-2(CO)(6); R = i-Pr, sec-Bu, cy-C6H11, p-MeC6H4) prepared from Fe-3(CO)(12), RSH, and Et3N were found to react in situ with iodobenzene or its substituted derivatives in the presence of the catalyst precursor Pd(PPh3)(4) to give the benzoyl type mu-acyl complexes (mu-RS)(mu-ArCO)Fe-2(CO)(6) (Ar = phenyl or substituted phenyl), whereas the in situ reactions of A [Et3NH] with iodo-substituted aromatic heterocycles under the same conditions afforded the corresponding heterocyclic type mu-acyl complexes (mu-RS)(mu-ArCO)Fe-2(CO)(6) (Ar = heterocyclic or benzoheterocyclic group). Particularly worth noting is that such Pd-catalyzed C-C bond cross-coupling reactions are the first examples of catalytic reactions regarding A [Et3NH] salts reported so far. In addition, all the prepared new mu-acyl complexes and the three new intermediate salts A [Et3NH] (R = i-Pr, sec-Bu, cy-C6H11) were isolated and structurally characterized, while a possible pathway for such type Pd-catalyzed reactions regarding A [Et3NH] salts is suggested.