1-phenylhept-2-yn-1-yl 2-(1H-indol-3-yl)acetate | 872884-96-3

• 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: 1-phenylhept-2-yn-1-yl 2-(1H-indol-3-yl)acetate
• 英文别名: 1-phenylhept-2-ynyl 2-(1H-indol-3-yl)acetate
• CAS: 872884-96-3
• 化学式: C₂₃H₂₃NO₂
• 分子量: 345.441
• InChiKey: LPWHAEWFDVQGRS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  42.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-phenylhept-2-yn-1-yl 2-(1H-indol-3-yl)acetate 在 Ph3PAuSbF6 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以98%的产率得到
  参考文献：
  名称：

  Tandem Au-Catalyzed 3,3-Rearrangement−[2 + 2] Cycloadditions of Propargylic Esters:  Expeditious Access to Highly Functionalized 2,3-Indoline-Fused Cyclobutanes

  摘要：

  The treatment of readily available propargylic indole-3-acetates with a catalytic amount of AuCl(PPh3)/AgSbF6 leads to tandem activations of the propargylic esters and the in situ generated allenylic esters, resulting in expeditious access to highly functionalized cyclobutanes with fused 2,3-indoline and gamma-lactone rings and an exocyclic E-double bond through sequential 3,3-rearrangement and [2 + 2] cyclization.

  DOI：

  10.1021/ja056419c
• 作为产物：
  描述：

  1-己炔 在 4-二甲氨基吡啶 、 正丁基锂 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 1-phenylhept-2-yn-1-yl 2-(1H-indol-3-yl)acetate
  参考文献：
  名称：

  Tandem Au-Catalyzed 3,3-Rearrangement−[2 + 2] Cycloadditions of Propargylic Esters:  Expeditious Access to Highly Functionalized 2,3-Indoline-Fused Cyclobutanes

  摘要：

  The treatment of readily available propargylic indole-3-acetates with a catalytic amount of AuCl(PPh3)/AgSbF6 leads to tandem activations of the propargylic esters and the in situ generated allenylic esters, resulting in expeditious access to highly functionalized cyclobutanes with fused 2,3-indoline and gamma-lactone rings and an exocyclic E-double bond through sequential 3,3-rearrangement and [2 + 2] cyclization.

  DOI：

  10.1021/ja056419c

文献信息

• Parameterization of Acyclic Diaminocarbene Ligands Applied to a Gold(I)-Catalyzed Enantioselective Tandem Rearrangement/Cyclization
  作者：Zachary L. Niemeyer、Suresh Pindi、Dimitri A. Khrakovsky、Christian N. Kuzniewski、Cynthia M. Hong、Leo A. Joyce、Matthew S. Sigman、F. Dean Toste

  DOI：10.1021/jacs.7b08791

  日期：2017.9.20

  are developed in the context of a gold catalyzed enantioselective tandem [3,3]-sigmatropic rearrangement-[2+2]-cyclization. Surrogate structures enable the rapid identification of parameters that reveal mechanistic characteristics. The observed selectivity trends are validated in a robust multivariate analysis facilitating the development of a highly enantioselective process.

  在金催化的对映选择性串联 [3,3]-sigmatropic 重排-[2+2]-环化的背景下开发了无环二氨基卡宾配体的计算描述符。替代结构能够快速识别揭示机械特性的参数。观察到的选择性趋势在稳健的多变量分析中得到验证，促进了高度对映选择性过程的发展。
• Gold Catalysis, Asymmetric Friedel–Crafts Alkylation Cascade for One-Pot Synthesis of Chiral Dihydrocarbazoles and Dihydrodibenzofurans
  作者：Xuan Wang、Ai-Hua Zhou、Tian-Qi Hu、Zhou Xu、Bo Zhou、Long-Wu Ye

  DOI：10.1021/acs.orglett.4c00311

  日期：2024.3.15

  A one-pot gold-catalyzed acyl migration followed by ytterbium-catalyzed asymmetric Friedel–Crafts alkylation is disclosed, leading to the rapid synthesis of chiral dihydrocarbazoles and dihydrodibenzofuran in generally moderate to good overall yields with good to excellent enantioselectivities. The gold-catalyzed acyl migration of propargyl acetates generates α-ylidene-β-diketones with high E/Z ratios

  公开了一锅金催化的酰基迁移，然后是镱催化的不对称弗里德尔-克来福特烷基化，导致手性二氢咔唑和二氢二苯并呋喃的快速合成，总体产率中等至良好，具有良好至优异的对映选择性。金催化乙酸炔丙酯的酰基迁移生成具有高E / Z比的 α-亚基-β-二酮，然后将其进行镱催化的不对称 Friedel-Crafts 烷基化，无需任何纯化。重要的是，该方案为不对称弗里德尔-克来福特烷基化提供了一种新型底物。
• Tandem Au-Catalyzed 3,3-Rearrangement−[2 + 2] Cycloadditions of Propargylic Esters:  Expeditious Access to Highly Functionalized 2,3-Indoline-Fused Cyclobutanes
  作者：Liming Zhang

  DOI：10.1021/ja056419c

  日期：2005.12.1

  The treatment of readily available propargylic indole-3-acetates with a catalytic amount of AuCl(PPh3)/AgSbF6 leads to tandem activations of the propargylic esters and the in situ generated allenylic esters, resulting in expeditious access to highly functionalized cyclobutanes with fused 2,3-indoline and gamma-lactone rings and an exocyclic E-double bond through sequential 3,3-rearrangement and [2 + 2] cyclization.