N-(5-叔丁基-2-羟基苯基)乙酰胺 | 17791-62-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: N-(5-叔丁基-2-羟基苯基)乙酰胺
• 英文名称: N-(5-(t-butyl)-2-hydroxyphenyl)acetamide
• 英文别名: 4-tert-butyl-2-acetamidophenol；N-(5-tert-butyl-2-hydroxyphenyl)acetamide
• CAS: 17791-62-7
• 化学式: C₁₂H₁₇NO₂
• mdl: MFCD01156590
• 分子量: 207.272
• InChiKey: BPTVKVHFORARFP-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：
  1.0
• sp3杂化的碳原子比例：
  0.416
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(5-叔丁基-2-羟基苯基)乙酰胺 在 三氯氧磷 、 sodium hydroxide 、 水 作用下， 以 氯仿 为溶剂， 以96%的产率得到5-(叔丁基)-2-甲基苯并噁唑
  参考文献：
  名称：

  2-和4-甲酰基吡啶并[2,1- b ]苯并恶唑的区域选择性合成

  摘要：

  在已知的化合物2-（苯并恶唑-2'-基）-3-二甲基氨基丙烯醛中，邻乙酰氨基酚（2）与Vilsmeier试剂在Meth-Cohn条件下反应生成2-甲酰基吡啶并[2,1- b ]苯并恶唑（5） （4）。在乙酸酐中回流4得到4-甲酰基吡啶并[2,1- b ]苯并恶唑（6），其为5的异构体。两个图5a和6a中进行了结构表征通过X射线晶体学。5的形成机理 提出了包括顺序氯化，二聚化，分子内去除HCl形成恶唑环，两次甲酰化以及区域选择性分子内亲核环化以构建吡啶酮环的方法。

  DOI：

  10.1021/jo900267c
• 作为产物：
  描述：

  乙酸酐 、 2-氨基-4-叔丁基酚 以 水 为溶剂， 以95%的产率得到N-(5-叔丁基-2-羟基苯基)乙酰胺
  参考文献：
  名称：

  2-和4-甲酰基吡啶并[2,1- b ]苯并恶唑的区域选择性合成

  摘要：

  在已知的化合物2-（苯并恶唑-2'-基）-3-二甲基氨基丙烯醛中，邻乙酰氨基酚（2）与Vilsmeier试剂在Meth-Cohn条件下反应生成2-甲酰基吡啶并[2,1- b ]苯并恶唑（5） （4）。在乙酸酐中回流4得到4-甲酰基吡啶并[2,1- b ]苯并恶唑（6），其为5的异构体。两个图5a和6a中进行了结构表征通过X射线晶体学。5的形成机理 提出了包括顺序氯化，二聚化，分子内去除HCl形成恶唑环，两次甲酰化以及区域选择性分子内亲核环化以构建吡啶酮环的方法。

  DOI：

  10.1021/jo900267c

文献信息

• Regioselective Syntheses of 2- and 4-Formylpyrido[2,1-<i>b</i>]benzoxazoles
  作者：Ke-Lai Li、Zong-Bo Du、Can-Cheng Guo、Qing-Yun Chen

  DOI：10.1021/jo900267c

  日期：2009.5.1

  o-Acetaminophenols (2) reacted with Vilsmeier reagent under Meth-Cohn conditions to yield 2-formylpyrido[2,1-b]benzoxazoles (5) unexpectedly besides the known compounds 2-(benzoxazol-2′-yl)-3-dimethylaminoacroleins (4). Refluxing 4 in acetic anhydride gave 4-formylpyrido[2,1-b]benzoxazoles (6), an isomer of 5. Both 5a and 6a were structurally characterized by X-ray crystallography. A mechanism for

  在已知的化合物2-（苯并恶唑-2'-基）-3-二甲基氨基丙烯醛中，邻乙酰氨基酚（2）与Vilsmeier试剂在Meth-Cohn条件下反应生成2-甲酰基吡啶并[2,1- b ]苯并恶唑（5） （4）。在乙酸酐中回流4得到4-甲酰基吡啶并[2,1- b ]苯并恶唑（6），其为5的异构体。两个图5a和6a中进行了结构表征通过X射线晶体学。5的形成机理 提出了包括顺序氯化，二聚化，分子内去除HCl形成恶唑环，两次甲酰化以及区域选择性分子内亲核环化以构建吡啶酮环的方法。
• Radical Carbonylation Mediated by Continuous-Flow Visible-Light Photocatalysis: Access to 2,3-Dihydrobenzofurans
  作者：Nenad Micic、Anastasios Polyzos

  DOI：10.1021/acs.orglett.8b01971

  日期：2018.8.3

  The annulative carbonylation of alkenyl-tethered arenediazonium salts using visible-light photocatalysis in continuous flow is described. The method furnishes a diverse series of novel acetate-functionalized 2,3-dihydrobenzofurans at room temperature and moderate CO pressure (25 atm), delivering these products in a short time with straightforward scale-up. This continuous flow and free-radical approach

  描述了在连续流中使用可见光光催化的链烯基系杂二氮杂鎓盐的环状羰基化。该方法在室温和适度的CO压力（25个大气压）下提供了一系列新的乙酸酯官能化的2,3-二氢苯并呋喃，可在短时间内以直接放大的方式提供这些产品。这种连续流动和自由基方法克服了传统的Pd催化环式羰基化的局限性，从而以可预测和区域选择性的方式提供了有价值的2,3-二氢苯并呋喃。
• IRREVERSIBLE INHIBITORS OF KRAS G12C MUTANT
  申请人：Max-Planck-Gesellschaft zur Förderung der Wissenschaften e.V.

  公开号：EP3628664A1

  公开（公告）日：2020-04-01

  The present invention relates to novel substituted 2-halopyrimidines and 5-halopyrazines, as well as pharmaceutical compositions containing at least one of these substituted 2-halopyrimidines or 5-halopyrazines together with at least one pharmaceutically acceptable carrier, excipient and/or diluent. Said substituted 2-halopyrimidines and 5-halopyrazines are covalently binding to KRas mutant G12C and therefore, are useful for the prophylaxis and treatment of cancer by direct inhibition of the KRas G12C-oncogenic signaling in cells.

  本发明涉及新型取代的 2-卤代嘧啶和 5-卤吡嗪，以及含有这些取代的 2-卤代嘧啶或 5-卤吡嗪中至少一种与至少一种药学上可接受的载体、赋形剂和/或稀释剂的药物组合物。所述取代的 2-卤代嘧啶和 5-卤吡嗪可与 KRas 突变体 G12C 共价结合，因此可通过直接抑制细胞中的 KRas G12C 致癌信号转导，用于预防和治疗癌症。
• Neutral Anion Receptors:  Synthesis and Evaluation as Sensing Molecules in Chemically Modified Field Effect Transistors
  作者：Martijn M. G. Antonisse、Bianca H. M. Snellink-Ruël、Isteyfo Yigit、Johan F. J. Engbersen、David N. Reinhoudt

  DOI：10.1021/jo9707040

  日期：1997.12.1

  A new class of anion selective receptors is based on the neutral uranylsalophene building block as Lewis acidic binding site. Additional hydrogen bond accepting or donating moieties near the anion binding site offer the possibility of varying the binding selectivity. Field effect transistors chemically modified with such receptors exhibit anion selectivities that strongly deviate from the classical Hofmeister series favoring phosphate or fluoride anions, depending on the structure of the uranylsalophenes. The phosphate selective chemically modified field effect transistors (CHEMFETs) detect phosphate with high selectivity over much more lipophilic anions, such as nitrate (log K-H2PO4,NO3(Pot) = -1.3), at [H2PO4-] greater than or equal to 6.3 x 10(-4) M. CHEMFETs modified with salophenes with amido substituents result in a high fluoride selectivity; even in the presence of 0.1 M chloride, fluoride can be detected at [F-] greater than or equal to 6 x 10(-4) M (log K-F,Cl(Pot) = -2.0).
• Reactions of phenols with thianthrene cation radical
  作者：Seung Rim Shin、Henry J. Shine

  DOI：10.1021/jo00035a031

  日期：1992.4

  The phenols 2-R1-6-R2-phenol 1a-g in which R1 = R2 = tert-butyl, methyl, isopropyl, Cl, Br, F, and H reacted with thianthrene cation radical perchlorate (Th.+ClO4-) to give 5-(4-hydroxyaryl)thianthreniumyl perchlorates 2a-g in good yield. o-Allylphenol (1i) behaved similarly. o-tert-Butylphenol (1h) gave both 5-(3-tert-butyl-4-hydroxyphenyl)thianthreniumyl perchlorate (2h) and a quinonoidal perchlorate (3), namely, 5-(3-thianthreniumyl-5-tert-butyl-6-oxo-2,4-cyclohexadien-1-ylidene)-5,5-dihydrothianthrene perchlorate. The 2,6-di-tert-butyl-4-R3-phenols 4a-c, R3 = tert-butyl, methoxy, and methyl, reacted with Th.+ClO4- in nitrile solvents (RCN) to give 2-R-5-R3-7-tert-butylbenzoxazoles 5a-e. The tert-butyl group that was displaced by RCN in forming 5 was converted into t-BuNHCOR (8), tert-butyl alcohol, and isobutene. In contrast, 2-tert-butyl-4,6-dimethylphenol (9) gave, in CH3CN, 4-tert-butyl-2,5,7-trimethylbenzoxazole (11), that is, with migration of the displaced tert-butyl group. The reactions of 4-tert-butylphenol (14) and 2,4-di-tert-butylphenol (17) are also described.