St_1g | 1382530-21-3

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物
• 英文名称: St_1g
• 英文别名: 3-[(4-Bromophenyl)methylidene]-5-phenylpent-4-yn-2-one
• CAS: 1382530-21-3
• 化学式: C₁₈H₁₃BrO
• 分子量: 325.205
• InChiKey: SFWMOYADUBWTTF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  St_1g 在 silver hexafluoroantimonate 、 1,3-双(2,6-二-异丙基苯基)咪唑-2-亚基金(I)氯化物 、 potassium carbonate 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 5.0h， 生成 3-((4-bromophenyl)(methoxy)methyl)-1-methoxy-2-methyl-5-phenyl-1H-pyrrole
  参考文献：
  名称：

  Gold(i)-catalyzed cyclization of 2-(1-alkynyl)-alk-2-en-1-one oximes: a facile access to highly substituted N-alkoxypyrroles

  摘要：

  已开发出一种金(I)催化的2-(1-炔基)-烷-2-烯-1-酮肟与众多核试剂环化反应的策略。该策略提供了一种相对安全、温和、简单的方法，用于获得大量高度取代的N-烷氧基吡咯。

  DOI：

  10.1039/c2cc32510a

文献信息

• Enantioselective Gold(I)-Catalyzed Heterocyclization–Intermolecular Exo [4 + 3]-Cycloaddition Reactions for the Synthesis of Chiral Oxa-Bridged Benzocycloheptanes
  作者：Xiaoyu Di、Yidong Wang、Lizuo Wu、Zhan-Ming Zhang、Qiang Dai、Wenbo Li、Junliang Zhang

  DOI：10.1021/acs.orglett.9b00537

  日期：2019.5.3

  The highly exo- and enantioselective gold-catalyzed tandem heterocyclization/[4 + 3] cycloaddition of 2-(1-alkynyl)-2-alken-1-ones and 1,3-diphenylisobenzofuran was implemented by utilizing Ming-Phos, which provides a facile access to chiral seven-membered oxa-bridged rings in 80–98% yield with high exo selectivity (exo/endo up to 50:1) and up to 97% ee.

  高度外切-和对映选择性金催化串联heterocyclization / [4 + 3] 2-（1-炔基）环加成-2-链烯-1-酮和1,3- diphenylisobenzofuran通过利用明-PHOS实现，其提供了容易获得手性七元氧杂桥环，产率为80-98％，具有高的外切选择性（外切/内切高达50：1）和ee高达97％。
• <scp>Ming‐Phos</scp>/Gold(I)‐Catalyzed Stereodivergent Synthesis of Highly Substituted Furo[3,4‐<i>d</i>][1,2]oxazines^†
  作者：Lujia Zhou、Bing Xu、Danting Ji、Zhan‐Ming Zhang、Junliang Zhang

  DOI：10.1002/cjoc.202000034

  日期：2020.6

  A gold(I)‐catalyzed asymmetric intermolecular tandem [3+3]‐cyclization reaction of 2‐(1‐alkynyl)‐2‐ alken‐1‐ones with nitrones has been developed by using Ming‐Phos as a chiral ligand. This method enables access to the stereodivergent synthesis of highly substituted furo[3,4‐d][1,2]oxazines in excellent efficiency and stereoselectivity (up to 99% yield, 99% ee, >20 : 1 dr).

  通过使用Ming-Phos作为手性配体开发了金（I）催化的2-（1-炔基）-2-链烯-1-酮与硝酮的不对称分子间串联[3 + 3]环化反应。该方法能够以优异的效率和立体选择性（高达99％的收率，99％ee，> 20：1 dr）获得高度取代的呋喃[3,4- d ] [1,2]恶嗪的立体发散性合成。
• Ming-Phos/Gold(I)-Catalyzed Diastereo- and Enantioselective Synthesis of Indolyl-Substituted Cyclopenta[<i>c</i>]furans
  作者：Yidong Wang、Zhan-Ming Zhang、Feng Liu、Yinyan He、Junliang Zhang

  DOI：10.1021/acs.orglett.8b02701

  日期：2018.10.19

  A highly enantioselective gold(I)-catalyzed intermolecular tandem cyclization/[3 + 2] cycloaddition of 2-(1-alkynyl)-2-alken-1-ones with 3-stylindoles was achieved by using Ming-Phos as a chiral ligand. A variety of chiral highly substituted cyclopenta[c]furans were obtained in good yields (up to 99%) with excellent diastereoselectivities (>20:1) and enantioselectivities (up to 97% ee). The salient

  通过使用Ming-Phos作为手性配体，实现了高对映选择性的金（I）催化的2-（1-炔基）-2-烯烃-1-酮与3-苯乙烯基吲哚的分子间串联环化/ [3 + 2]环加成反应。以良好的非对映选择性（> 20：1）和对映选择性（高达ee的97％）获得了高收率（高达99％）的各种手性高度取代的环戊[ c ]呋喃。使用容易获得的起始原料和手性配体，本方案的显着特征包括温和的条件，优异的收率以及高的非对映和对映选择性。
• Furan‐Based <i>o‐</i> Quinodimethanes by Gold‐Catalyzed Dehydrogenative Heterocyclization of 2‐(1‐Alkynyl)‐2‐alken‐1‐ones: A Modular Entry to 2,3‐Furan‐Fused Carbocycles
  作者：Liejin Zhou、Mingrui Zhang、Wenbo Li、Junliang Zhang

  DOI：10.1002/anie.201403709

  日期：2014.6.16

  strategy for in situ generation of furan‐based ortho‐quinodimethanes (o‐QDMs) by the gold(I)‐mediated dehydrogenative heterocyclization of 2‐(1‐alkynyl)‐2‐alken‐1‐ones in the presence of pyridine N‐oxide under mild reaction conditions was developed. These in situ furan‐based o‐QDMs were trapped by electron‐deficient olefins and alkynes, thus furnishing various 2,3‐furan‐fused carbocycles in good yields

  在吡啶N存在下，金（I）介导的2-（1-炔基）-2-烯键-1-酮的氢脱氢杂环化反应原位生成呋喃基邻喹啉二甲烷（o -QDMs）的策略在温和的反应条件下产生了氧化物。这些原位基于呋喃的o - QDM被缺电子的烯烃和炔烃捕获，从而以高收率提供了各种具有高非对映选择性和区域选择性的各种2,3-呋喃融合的碳环。
• Enantioselective Synthesis of 4<i>H</i>-Pyrans Through Organocatalytic Asymmetric Formal [3+3] Cycloadditions of 2-(1-Alkynyl)-2-alken-1-ones with β-Keto Esters
  作者：Zhenting Yue、Wenbo Li、Lu Liu、Cuihong Wang、Junliang Zhang

  DOI：10.1002/adsc.201600591

  日期：2016.10.6

  4H‐Pyran units are frequently present in molecules with significant biological and pharmaceutical activities. Herein, we present the first enantioselective formal [3+3] cycloaddition between 2‐(1‐alkynyl)‐2‐alken‐1‐ones and β‐keto esters catalyzed by a cyclohexyldiamine‐based thiourea‐tertiary amine bifunctional catalyst. Under the mild and eco‐friendly conditions, a wide range of polysubstituted 4H‐pyrans

  4 H- Pyran单元经常存在于具有重要生物学和药学活性的分子中。本文中，我们介绍了由环己基二胺基硫脲叔胺双功能催化剂催化的2-（1-炔基）-2-链烯-1-酮与β-酮酯之间的首次对映选择性形式[3 + 3]环加成反应。在温和且生态友好的条件下，以中等收率和良好的对映选择性获得了多种多取代的4 H-吡喃。