1-苄基-2-丁基吲哚 | 87587-40-4

• 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: 1-苄基-2-丁基吲哚
• 英文名称: 1-benzyl-2-butyl-1H-indole
• 英文别名: 1-benzyl-2-butylindole；N-benzyl-2-butylindole
• CAS: 87587-40-4
• 化学式: C₁₉H₂₁N
• 分子量: 263.382
• InChiKey: JBKRDAQGHMMBRE-UHFFFAOYSA-N

物化性质

• 沸点：
  426.4±24.0 °C(Predicted)
• 密度：
  1.00±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  4.9
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  N-benzyl-N-phenyl-O-(trimethylsilyl)hydroxylamine 在 copper(l) iodide 、 calcium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 1-苄基-2-丁基吲哚
  参考文献：
  名称：

  Nucleophilic aromatic substitution by organoaluminum reagents. Application to the synthesis of indoles

  摘要：

  DOI：

  10.1021/ja00362a030

文献信息

• Borane-catalyzed indole synthesis through intramolecular hydroamination
  作者：Sebastian Tussing、Miriam Ohland、Garrit Wicker、Ulrich Flörke、Jan Paradies

  DOI：10.1039/c6dt04725d

  日期：——

  The reaction of 2-alkynyl anilines with catalytic amounts of B(C6F5)3 (5 mol%) resulted in the formation of 2-substituted indoles according to an intramolecular hydroamination in good to excellent yields. Reaction intermediates as well as products were characterized by NMR spectroscopy and by X-ray crystallography. The domino hydroamination/hydrogenation sequence allowed the efficient synthesis of

  2-炔基苯胺与催化量的B（C 6 F 5）3（5mol％）的反应根据分子内加氢胺化以良好或优异的产率形成了2-取代的吲哚。反应中间体和产物通过NMR光谱和X射线晶体学表征。多米诺加氢胺化/加氢序列允许以高收率有效地合成四氢喹啉8。
• 2,3-Disubstituted Benzofuran and Indole by Copper-Mediated C−C Bond Extension Reaction of 3-Zinciobenzoheterole
  作者：Masaharu Nakamura、Laurean Ilies、Saika Otsubo、Eiichi Nakamura

  DOI：10.1021/ol060896y

  日期：2006.6.1

  [reaction: see text] A metalative 5-endo-dig cyclization reaction of 2-ynylphenoles or anilines effected by BuLi and ZnCl(2) produces 3-zinciobenzoheteroles in excellent yield. These intermediates have been transmetalated to the corresponding cuprates and allowed to react with electrophiles to produce a variety of 2,3-disubstituted benzofurans and indoles.

  [反应：参见文本]由BuLi和ZnCl（2）引起的2-炔基苯酚或苯胺的金属化5内-dig环化反应以极好的收率产生3-zinciobenzoheteroles。这些中间体已被金属转移成相应的铜酸盐，并使其与亲电子试剂反应生成各种2，3-二取代的苯并呋喃和吲哚。
• Simple Indole Synthesis by One-Pot Sonogashira Coupling-NaOH-Mediated Cyclization
  作者：Roberto Sanz、Verónica Guilarte、M. Castroviejo

  DOI：10.1055/s-0028-1083624

  日期：2008.12

  Coupling of o-iodoanilines with terminal alkynes under standard Sonogashira conditions, and further treatment with NaOH under conventional heating or microwave irradiation, afford 2-substituted indoles in usually high yields. Functionalities such as halides, nitro, and cyano groups are tolerated under the reaction conditions.

  在标准Sonogashira条件下，将o-碘苯胺与末端炔烃偶联，并在常规加热或微波辐照下进一步处理NaOH，通常可以获得高产率的2-取代吲哚。在反应条件下，卤素、硝基和氰基等功能团均可耐受。
• Efficient Synthesis of 2-Substituted Indoles Based on Palladium(II) Acetate/Tri-tert-butylphosphine-Catalyzed Alkynylation/Amination of 1,2-Dihalobenzenes
  作者：Zhen-Yu Tang、Qiao-Sheng Hu

  DOI：10.1002/adsc.200606022

  日期：2006.5

  A simple, efficient palladium(II) acetate/tri-tert-butylphosphine-catalyzed indole synthesis from o-alkynylhalobenzenes, readily available from 1,2-dihalobenzenes, has been achieved in good to excellent yields. A one-pot, Pd(OAc)2/t-Bu3P-catalyzed sequential reaction from 1-chloro-2-iodobenzene, phenylacetylene and amines has also been achieved in good yields.

  由邻-炔基卤代苯简单，有效的乙酸钯（II）/三叔丁基膦催化的吲哚合成，可以容易地从1,2-二卤代苯获得，收率良好至极佳。还已经以良好的产率实现了由1-氯-2-碘苯，苯乙炔和胺进行的一锅法Pd（OAc）2 / t - Bu 3 P催化的顺序反应。
• Synthesis and Catalytic Activity of Coumarin‐ and Chrysin‐Tethered Triazolylidene Gold(I) Complexes
  作者：Francisco J. Ruiz‐Mendoza、Daniel Mendoza‐Espinosa、Simplicio González‐Montiel

  DOI：10.1002/ejic.201800921

  日期：2018.11.15

  chrysin‐functionalized triazolium salts (2,3) have been synthesized stepwise via copper catalyzed alkyne–azide cycloaddition and N‐alkylation procedures. Their one‐pot deprotonation with KHMDS in presence of AuCl(SMe2) allowed for the preparation of the corresponding triazolylidene gold(I) complexes (4–6) in high yields (75–92 %). All new compounds were fully characterized by means of 1H and 13C NMR spectroscopy

  一系列空间位作保香豆素（1）和白杨素官能化的三唑鎓盐（2，3）已经通过铜催化炔叠氮化物环加成和合成逐步Ñ烷基化方法。他们在AuCl（SMe 2）存在下用KHMDS进行一锅式去质子反应，从而可以高产率（75-92％）制备相应的三唑基亚金（I）配合物（4-6）。所有新化合物均通过1 H和13 C NMR光谱，FT-IR，元素分析以及在三唑F，三唑鎓1和金络合物4的情况下得到充分表征。，通过单晶X射线衍射。通过几种容易获得的苯胺的分子内加氢胺化反应，将新的三唑基亚金配合物（4-6）作为吲哚衍生物合成中的前催化剂进行了测试。