3,4-dihydronaphthalen-1(2H)-one O-acetyl oxime | 28353-74-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: 3,4-dihydronaphthalen-1(2H)-one O-acetyl oxime
• 英文别名: α-tetralone O-acetyl oxime；(3,4-dihydro-2H-naphthalen-1-ylideneamino) acetate
• CAS: 28353-74-4
• 化学式: C₁₂H₁₃NO₂
• 分子量: 203.241
• InChiKey: POJRXDJUQGTWKN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  38.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3,4-dihydronaphthalen-1(2H)-one O-acetyl oxime 在 palladium diacetate 、 potassium carbonate 、 三环戊基膦 作用下， 以 甲苯 为溶剂， 反应 8.0h， 以62%的产率得到1-萘胺
  参考文献：
  名称：

  Pd-Catalyzed Semmler–Wolff Reactions for the Conversion of Substituted Cyclohexenone Oximes to Primary Anilines

  摘要：

  Homogeneous Pd catalysts have been identified for the conversion of cyclohexenone and tetralone O-pivaloyl oximes to the corresponding primary anilines and 1-aminonaphthalenes. This method is inspired by the Semmler-Wolff reaction, a classic method that exhibits limited synthetic utility owing to its forcing conditions, narrow scope, and low product yields. The oxime N-O bond undergoes oxidative addition to Pd-0(PCy3)(2), and the product of this step has been characterized by X-ray crystallography and shown to undergo dehydrogenation to afford the aniline product.

  DOI：

  10.1021/ja4073172
• 作为产物：
  描述：

  四酮-1-肟 生成 3,4-dihydronaphthalen-1(2H)-one O-acetyl oxime
  参考文献：
  名称：

  Schroeter et al., Chemische Berichte, 1930, vol. 63, p. 1308,1325

  摘要：

  DOI：

文献信息

• Copper catalyzed five-component domino strategy for the synthesis of nicotinimidamides
  作者：Yu Zhao、Li Li、Zitong Zhou、Man Chen、Weiguang Yang、Hui Luo

  DOI：10.1039/d1ob00162k

  日期：——

  synthesized by a copper-catalyzed multicomponent domino reaction of oxime esters, terminal ynones, sulfonyl azides, aryl aldehydes and acetic ammonium. Its synthetic pathway involves the formation of a highly reactive N-sulfonyl acetylketenimine, characterized by high selectivity, combinations of potential nucleophiles and electrophiles, mild reaction conditions and a wide substrate scope, and is a rare

  通过肟酯、末端炔酮、磺酰叠氮化物、芳基醛和乙酸铵的铜催化多组分多米诺反应合成了药用和合成重要的烟酰胺库。其合成途径涉及形成高反应性的N-磺酰基乙酰酮亚胺，具有选择性高、潜在的亲核试剂和亲电试剂组合、反应条件温和、底物范围广等特点，是少有的CuAAC/环五组分实例。打开反应。
• Iron-Catalyzed Synthesis of 2<i>H</i>-Imidazoles from Oxime Acetates and Vinyl Azides under Redox-Neutral Conditions
  作者：Zhongzhi Zhu、Xiaodong Tang、Jianxiao Li、Xianwei Li、Wanqing Wu、Guohua Deng、Huanfeng Jiang

  DOI：10.1021/acs.orglett.7b00203

  日期：2017.3.17

  A novel and versatile method for the synthesis of 2H-imidazoles via iron-catalyzed [3 + 2] annulation from readily available oxime acetates with vinyl azides has been developed. This denitrogenative process involved N–O/N–N bond cleavages and two C–N bond formations to furnish 2,4-substituted 2H-imidazoles. This protocol was performed under mild reaction conditions and needed no additives or ligands

  已开发出一种新颖且通用的方法，该方法通过铁催化的[3 + 2]环合反应从易于获得的肟肟与叠氮化乙烯中合成2 H-咪唑。该脱氮过程涉及N–O / N–N键断裂和两个C–N键形成，以提供2,4-取代的2 H-咪唑。该方案在温和的反应条件下进行，不需要添加剂或配体。此外，这是绿色反应，涉及乙酸肟肟作为内部氧化剂，乙酸和氮作为副产物。
• Copper-catalyzed synthesis of thiazol-2-yl ethers from oxime acetates and xanthates under redox-neutral conditions
  作者：Zhongzhi Zhu、Xiaodong Tang、Jinghe Cen、Jianxiao Li、Wanqing Wu、Huanfeng Jiang

  DOI：10.1039/c8cc00445e

  日期：——

  acetates and xanthates for the synthesis of thiazol-2-yl ethers with remarkable regioselectivity has been developed. Various oxime acetates, whether derived from aryl ketones or alkyl ketones, or natural product cores are suitable for this conversion. Unique dihydrothiazoles were also obtained when both reaction sites were methine. Mechanistic studies indicated that imino copper(III) intermediates were involved

  新型的铜催化的肟肟酸酯和黄药酸酯的环化反应用于合成噻唑-2-基醚，具有显着的区域选择性。各种衍生自芳基酮或烷基酮的乙酸肟酯，或天然产物核均适用于该转化。当两个反应位点均为次甲基时，也获得了独特的二氢噻唑。机理研究表明，涉及亚氨基铜（III）中间体。另外，该方案在氧化还原中性条件下进行，不需要添加剂或配体。
• Synthesis of enaminones via copper-catalyzed decarboxylative coupling reaction under redox-neutral conditions
  作者：Zhongzhi Zhu、Xiaodong Tang、Jianxiao Li、Xianwei Li、Wanqing Wu、Guohua Deng、Huanfeng Jiang

  DOI：10.1039/c7cc00260b

  日期：——

  A novel copper-catalyzed C(sp3)-H oxidative functionalization of aromatic oxime acetates with [small alpha]-oxocarboxylic acids was reported. This process involved N-O/C-C bond cleavages and C-C bond formations to furnish substituted enaminones under...

  报道了用小α-氧代羧酸对芳族肟乙酸酯的新型铜催化的C（sp3）-H氧化官能化。该过程涉及NO / CC键的裂解和CC键的形成，以在...下提供取代的烯胺。
• Cu-Catalyzed Coupling of <i>O</i> -Acyl Oximes with Isatins: Domino Rearrangement Strategy for Direct Access to Quinoline-4-Carboxamides by C-N Bond Cleavage
  作者：Andhavaram Ramaraju、Neeraj Kumar Chouhan、Owk Ravi、Balasubramanian Sridhar、Surendar Reddy Bathula

  DOI：10.1002/ejoc.201800501

  日期：2018.6.22

  A mild domino rearrangement strategy for the direct access to substituted quinoline‐4‐carboxamides has been developed. This copper‐catalyzed coupling reaction of O‐acyl oximes with isatins in the presence of molecular oxygen as the sole oxidizing agent proceeds through a ring expansion of the isatins through cleavage of the two CN bonds

  已经开发了一种用于直接获得取代的喹啉-4-甲酰胺的温和多米诺重排策略。O-酰基肟与靛红在分子氧存在下的铜催化偶联反应，作为唯一氧化剂，通过两个 CN 键的断裂使靛红环膨胀进行