(2Z)-2-[(E)-3-phenylprop-2-enylidene]-3,4-dihydropyrazol-2-ium-5-olate

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2Z)-2-[(E)-3-phenylprop-2-enylidene]-3,4-dihydropyrazol-2-ium-5-olate
• 化学式: C₁₂H₁₂N₂O
• 分子量: 200.24
• InChiKey: ZDWUFNDKQGRCKA-DBBRDBGQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  38.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2Z)-2-[(E)-3-phenylprop-2-enylidene]-3,4-dihydropyrazol-2-ium-5-olate 在 dirhodium tetrakis(caprolactamate) 、 scandium tris(trifluoromethanesulfonate) 作用下， 以 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 反应 16.0h， 生成 methyl 5-(tert-butyldimethylsilyl)oxy-3-oxo-8-[(E)-styryl]-2,3,7,8-tetrahydro-1Hpyrazolo[1,2-a]pyridazine-6-carboxylate
  参考文献：
  名称：

  β-亚甲基-β-甲硅烷氧基-β-酰胺基-α-重氮乙酸酯的高度选择性依赖于催化剂的竞争性 1,2-C→C、-O→C 和 -N→C 迁移

  摘要：

  过渡金属催化剂以高选择性引导 1,2-C→C、-O→C 和 -N→C 从 β-亚甲基-β-甲硅烷氧基-β-酰胺基-α-重氮乙酸盐迁移。实现这种独特的差异选择性显示的关键依赖于其催化生成的金属卡宾的空间和立体电子控制。

  DOI：

  10.1021/ja311392m

文献信息

• Metal Amides as the Simplest Acid/Base Catalysts for Stereoselective Carbon-Carbon Bond-Forming Reactions
  作者：Yasuhiro Yamashita、Shū Kobayashi

  DOI：10.1002/chem.201300908

  日期：2013.7.15

  paper, new possibilities for metal amides are described. Although typical metal amides are recognized as strong stoichiometric bases for deprotonation of inert or less acidic hydrogen atoms, transition‐metal amides, namely silver and copper amides, show interesting abilities as one of the simplest acid/base catalysts in stereoselective carbon–carbon bond‐forming reactions.

  在本文中，描述了金属酰胺的新可能性。尽管公认典型的金属酰胺是惰性或弱酸性氢原子去质子化的强化学计量基础，但过渡金属酰胺（即银和铜酰胺）作为立体选择性碳-碳键中最简单的酸/碱催化剂之一显示出令人感兴趣的功能。形成反应。
• Facile and efficient synthesis of indazole derivatives by 1,3-cycloaddition of arynes with diazo compounds and azomethine imides
  作者：Tienan Jin、Fan Yang、Yoshinori Yamamoto

  DOI：10.1135/cccc2009014

  日期：——

  N-Unsubstituted indazoles 3 and 1-arylindazoles 4 are readily available in good to high yields through [3+2] cycloaddition of 2-(trimethylsilyl)aryl triflates 1 and diazo compounds in the presence of KF or CsF under mild reaction conditions. Furthermore, we found that azomethine imides also underwent cycloaddition reaction with 2-(trimethylsilyl)phenyl triflates (1a) in the presence of KF to afford indazolone derivatives 6 in moderate yields.

  N-未取代吲唑3和1-芳基吲唑4可通过2-(三甲基硅基)芳基三氟甲烷磺酸酯1和重氮化合物在KF或CsF存在下在温和反应条件下进行[3+2]环加成反应，以良好至高产率方便获得。此外，我们发现偶氮亚甲基亚胺也可在KF存在下与2-(三甲基硅基)苯基三氟甲烷磺酸酯（1a）发生环加成反应，得到吲唑酮衍生物6，产率中等。
• Highly enantioselective phosphination and hydrophosphonylation of azomethine imines: using chiral squaramide as a hydrogen bonding organocatalyst
  作者：Ling-Pei Kong、Nai-Kai Li、Shao-Yun Zhang、Xiang Chen、Min Zhao、Ya-Fei Zhang、Xing-Wang Wang

  DOI：10.1039/c4ob01472c

  日期：——

  Enantioselective phosphination and hydrophosphonylation reactions between azomethine imines and diarylphosphine oxides or dialkyl phosphites were respectively developed by the use of a chiral squaramide as the hydrogen bonding organocatalyst, which afforded two types of phosphorus containing product in high yields with good to excellent enantioselectivities.

  采用手性方形酰胺作为氢键有机催化剂，分别开发了亚硝基亚胺与二芳基膦氧化物或二烷基膦酸酯之间的对映选择性磷化和氢膦化反应，这两种反应均可高产率地获得两种含磷产品，且对映选择性良好至优异。
• Expeditious Synthesis of Trifluoromethylated Heterocycles: Noncatalytic 1,3-Dipolar Cyclization of Azomethine Imines with (α-Trifluoromethyl)acrylates
  作者：Norio Shibata、Shinichi Ogawa、Takayuki Nishimine、Etsuko Tokunaga

  DOI：10.1055/s-0030-1258189

  日期：2010.10

  A convenient, simple, and expeditious procedure for the preparation of novel trifluoromethylated bicyclic pyrazolidinone systems by noncatalytic 1,3-dipolar cyclization of azomethine imines­ with tert-butyl 2-(trifluoromethyl)prop-2-enoate is presented.

  本文提出了一种方便、简单且快速的制备新型三氟甲基化二环噻唑啉酮系统的程序，采用非催化的1,3-极化环化反应，将亚胺烯与叔丁基2-(三氟甲基)丙-2-烯酸酯反应。
• 1,5,7-Triazabicyclo[4.4.0]dec-5-ene (TBD) Triggered Diastereoselective [3+2] Cycloaddition of Azomethine Imines and Pyrazoleamides
  作者：Chiara Volpe、Sara Meninno、Amedeo Capobianco、Giovanni Vigliotta、Alessandra Lattanzi

  DOI：10.1002/adsc.201801567

  日期：2019.3.5

  2‐a]‐pyrazole‐1,7‐diones, bearing up to three stereocentres, by reacting ready available N,N′‐cyclic azomethine imines and pyrazoleamides under catalytic loading of commercial 1,5,7‐triazabicyclo[4.4.0]dec‐5‐ene (TBD), has been developed. The products are obtained in good yields and high diastereoselectivity, working at room temperature. Preliminary bioassay showed the products to inhibit growth of Gram‐positive

  一种实用且温和的方法，通过在市售催化剂1的催化负载下，使现成的N，N'-环偶氮甲亚胺和吡唑酰胺反应，制得多达三个立体中心的四氢吡唑并[1,2-a]-吡唑-1,7-二酮。已开发了5,5,7-三氮杂双环[4.4.0] dec-5-ene（TBD）。在室温下工作时，以高收率和高非对映选择性获得产物。初步的生物测定显示该产品抑制了革兰氏阳性细菌的生长。