2-(3'-nitrophenyl)indole-1-carboxylic acid tert-butyl ester

• 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: 2-(3'-nitrophenyl)indole-1-carboxylic acid tert-butyl ester
• 英文别名: 2-(3-nitrophenyl)-1H-indole-1-carboxylic acid 1,1-dimethylethyl ester；Tert-butyl 2-(3-nitrophenyl)indole-1-carboxylate；tert-butyl 2-(3-nitrophenyl)indole-1-carboxylate
• 化学式: C₁₉H₁₈N₂O₄
• 分子量: 338.363
• InChiKey: YZAPSAGUULKHSC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  77
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1-Boc-吲哚 在 tris(dibenzylideneacetone)dipalladium(0) chloroform complex 、 copper(l) iodide 、 sodium t-butanolate 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 30.17h， 生成 2-(3'-nitrophenyl)indole-1-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  2-吲哚基二甲基硅烷醇与取代的芳基卤化物的钯催化交叉偶联反应。

  摘要：

  [反应：见正文]已经开发了2-吲哚基硅烷醇的温和且普遍的交叉偶联反应。导致成功偶联的实验变量是（1）使用叔丁醇钠作为活化剂;（2）使用化学计量的碘化亚铜（I）;以及（3）使用Pd2（dba）3 .CHCl3作为催化剂。在这些条件下，N-（Boc）-2-吲哚基二甲基硅烷醇与多种芳族碘化物反应，以良好的收率（70-84％）提供偶联产物。

  DOI：

  10.1021/ol048328a

文献信息

• Synthesis of 2-Substituted Indoles and Indolines via Suzuki−Miyaura Coupling/5-<i>endo</i>-<i>trig</i> Cyclization Strategies
  作者：Haruhiko Fuwa、Makoto Sasaki

  DOI：10.1021/jo801985a

  日期：2009.1.2

  preparation of various N-(o-halophenyl)enecarbamates that served as useful precursors for subsequent 5-endo-trig Heck or 5-endo-trig aryl radical cyclizations to furnish 2-substituted indoles or indolines, respectively. Furthermore, a one-pot Suzuki−Miyaura coupling−cyclization cascade starting from enol phosphates has been developed, which was successfully applied to the efficient synthesis of an in

  基于Suzuki-Miyaura偶联-环化序列，已经开发了使用无环，酰亚胺衍生的烯醇磷酸酯合成2-取代的吲哚和二氢吲哚的新策略，这些磷酸酯很容易由邻卤代苯胺制备。高度化学选择性的交叉偶联酰亚胺衍生的烯醇磷酸盐与允许的各种有效制备铃木-宫浦条件下亲核试剂硼ñ - （ö -halophenyl）enecarbamates其充当用于随后的5-有用前体内切-三角函数的Heck或5 -内-三角芳基环化分别提供2-取代的吲哚或二氢吲哚。此外，已经开发了从烯醇磷酸酯开始的一锅Suzuki-Miyaura偶联-环化级联反应，该反应已成功地用于有效合成吲哚-2-基-1 H-喹啉-2-酮KDR抑制剂。
• Palladium-Catalyzed Cross-Coupling of Five-Membered Heterocyclic Silanolates
  作者：Scott E. Denmark、John D. Baird、Christopher S. Regens

  DOI：10.1021/jo7023784

  日期：2008.2.1

  The preparation of pi-rich 2-aryl heterocycles by palladium-catalyzed cross-coupling of sodium heteroarylsilanolates with aryl iodides, bromides, and chlorides is described. The cross-coupling process was developed through extensive optimization of the following key variables: (1) identification of stable, isolable alkali metal silanolates, (2) identification of conditions for preformation and isolation of silanolate salts, (3) judicious choice in the palladium catalyst/ligand combination, and (4) selection of the protecting group on the nitrogen of indole. It was found that the alkali metal silanolates, either isolated or formed in situ, offered a significant rate enhancement and broader substrate scope over the use of silanols activated by Bronsted bases such as NaOt-Bu. In addition, the optimized conditions for the cross-coupling of 2-indolylsilanolates were readily applied to the cross-coupling of 2-pyrrolyl-, 2-furyl-, and 2-thienylsilanolates.
• Palladium-Catalyzed Cross-Coupling Reactions of 2-Indolyldimethylsilanols with Substituted Aryl Halides
  作者：Scott E. Denmark、John D. Baird

  DOI：10.1021/ol048328a

  日期：2004.9.1

  [reaction: see text] A mild and general cross-coupling reaction of 2-indolylsilanols has been developed. The experimental variables that lead to successful coupling are (1) the use of sodium tert-butoxide as the activator, (2) the use of copper(I) iodide in stoichiometric quantities, and (3) the use of Pd2(dba)3.CHCl3 as the catalyst. Under these conditions N-(Boc)-2-indolyldimethylsilanol reacts with

  [反应：见正文]已经开发了2-吲哚基硅烷醇的温和且普遍的交叉偶联反应。导致成功偶联的实验变量是（1）使用叔丁醇钠作为活化剂;（2）使用化学计量的碘化亚铜（I）;以及（3）使用Pd2（dba）3 .CHCl3作为催化剂。在这些条件下，N-（Boc）-2-吲哚基二甲基硅烷醇与多种芳族碘化物反应，以良好的收率（70-84％）提供偶联产物。