Anthranilsaeurebut-3-ynylamid | 33238-75-4

• 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: Anthranilsaeurebut-3-ynylamid
• 英文别名: 2-amino-N-(but-3-yn-1-yl)benzamide；2-amino-N-but-3-ynylbenzamide
• CAS: 33238-75-4
• 化学式: C₁₁H₁₂N₂O
• 分子量: 188.229
• InChiKey: SEZTUYFDMLGDLO-UHFFFAOYSA-N

物化性质

• 沸点：
  398.0±27.0 °C(Predicted)
• 密度：
  1.138±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  55.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  Anthranilsaeurebut-3-ynylamid 在 氯[2-(二叔丁基磷)二苯基]金 、 magnesium sulfate 、 potassium carbonate 、 对甲苯磺酸 、 双三氟甲烷磺酰亚胺银盐 作用下， 以 四氢呋喃 、 甲醇 、 1,2-二氯乙烷 为溶剂， 反应 10.5h， 生成 2-methyl-7'-methylene-8',9'-dihydro-7'H,11'H-spiro[indole-3,6'-pyrido[2,1-b]quinazolin]-11'-one
  参考文献：
  名称：

  Synthesis of spiroindolenine-3,3′-pyrrolo[2,1-b]quinazolinones through gold(i)-catalyzed dearomative cyclization of N-alkynyl quinazolinone-tethered indoles

  摘要：

  报道了一种高效的金(i)催化的脱芳香环化反应，用于制备各种螺吡咯[2,1-b]喹唑酮的衍生物，该反应中使用了N-炔基喹唑酮-拴联C2-取代吲哚，产率良好至优秀。

  DOI：

  10.1039/d1ob02492b
• 作为产物：
  描述：

  靛红酸酐 、 1-氨基-3-丁炔 以 N,N-二甲基甲酰胺 为溶剂， 生成 Anthranilsaeurebut-3-ynylamid
  参考文献：
  名称：

  One-Pot Synthesis of Luotonin A and Its Analogues

  摘要：

  Starting with inexpensive reagents, a self-directed chemical process with the aid of a single metal triflate was readily achieved to concomitantly construct quinazoline and pyrroloquinoline cores to afford the synthesis of luotonin A and its analogues. Among all compounds prepared, 2c, 2d, and 3b exhibit more potent inhibitory activity than luotonin A against human topoisomerase I.

  DOI：

  10.1021/ol1029707

文献信息

• Gold(I)‐Catalyzed Selective Cyclization and 1,2‐Shift to Prepare Pseudorutaecarpine Derivatives
  作者：Wang Wang、Nan‐Ying Chen、Pei‐Sen Zou、Li Pang、Dong‐Liang Mo、Cheng‐Xue Pan、Gui‐Fa Su

  DOI：10.1002/adsc.202101054

  日期：2022.2.15

  pseudorutaecarpine derivatives were prepared in good to excellent yields through a gold(I)-catalyzed selective cyclization and 1,2-shift of N-alkynyl quinazolinone-tethered indoles. Mechanistic study revealed that spiroindolenines generated in situ by cyclization at the the indole C3 position underwent an alkenyl 1,2-shift to generate pseudorutaecarpine. The reaction proceeds under mild reaction conditions

  通过金 (I) 催化的选择性环化和N-炔基喹唑啉酮系链吲哚的 1,2-位移，以良好至优异的产率制备了多种假芸香碱衍生物。机理研究表明，通过在吲哚C3位环化原位产生的螺二氢吲哚经过烯基1,2-移位生成假芸香碱。该反应在温和的反应条件下进行，具有广泛的底物范围、良好的官能团耐受性和克级规模的应用。此外，生物学评估表明，大多数制备的假芸香碱支架具有抗炎活性。
• Synthesis of 4-(trichloromethyl)pyrido[2′,1′:3,4]pyrazino[2,1-<i>b</i>]quinazolinones through a cyclized dearomatization and trichloromethylation cascade strategy
  作者：Xu Zhang、Meng-Yan Wei、Jun-Cheng Su、Cui Liang、Cheng-Xue Pan、Gui-Fa Su、Dong-Liang Mo

  DOI：10.1039/d3ob02084c

  日期：——

  A variety of 4-(trichloromethyl)pyrido[2′,1′:3,4]pyrazino[2,1-b]quinazolinones were prepared in moderate to good yields with high regioselectivity through intramolecular 6-endo-dig cyclization and trichloromethylation of N3-alkynyl-2-pyridinyl-tethered quinazolinones in chloroform. Mechanistic studies revealed that chloroform might serve as a trichloromethyl anion precursor. Furthermore, the reaction

  通过分子内6-内环化和三氯甲基化，以中等至良好的产率和高区域选择性制备了多种4-(三氯甲基)吡啶并[2',1':3,4]吡嗪并[2,1- b ]喹唑啉酮。 N 3-炔基-2-吡啶基束缚的喹唑啉酮在氯仿中。机理研究表明，氯仿可能作为三氯甲基阴离子前体。此外，该反应可以很容易地在克级进行，并且通过五个步骤制备了雌酮衍生的4-(三氯甲基)吡啶并[2',1':3,4]吡嗪并[2,1- b ]喹唑啉酮。该方法具有底物范围广、官能团耐受性好、吡啶环脱芳构化新、三氯甲基化试剂为氯仿等特点。
• [EN] NEW N-ALKYNYLBENZAMIDE DERIVATIVES<br/>[FR] NOUVEAUX DÉRIVÉS DE N-ALKYNYLBENZAMIDE
  申请人：BAYER CROPSCIENCE AG

  公开号：WO2008081016A1

  公开（公告）日：2008-07-10

  [EN] A compound of general formula (I) A process for preparing this compound. A fungicidal composition comprising a compound of general formula (I). A method for treating plants by applying a compound of general formula (I) or a composition comprising it.
  [FR] L'invention concerne un composé de formule générale (I), une méthode de préparation du composé, une composition fongicide comprenant un composé de formule générale (I), un procédé de traitement de plantes par application d'un composé de formule générale (I) ou d'une composition comprenant ce composé.
• One-Pot Synthesis of Luotonin A and Its Analogues
  作者：Ming-Chung Tseng、Yu-Wan Chu、Hsiang-Ping Tsai、Chun-Mao Lin、Jaulang Hwang、Yen-Ho Chu

  DOI：10.1021/ol1029707

  日期：2011.3.4

  Starting with inexpensive reagents, a self-directed chemical process with the aid of a single metal triflate was readily achieved to concomitantly construct quinazoline and pyrroloquinoline cores to afford the synthesis of luotonin A and its analogues. Among all compounds prepared, 2c, 2d, and 3b exhibit more potent inhibitory activity than luotonin A against human topoisomerase I.
• Synthesis of spiroindolenine-3,3′-pyrrolo[2,1-<i>b</i>]quinazolinones through gold(<scp>i</scp>)-catalyzed dearomative cyclization of <i>N</i>-alkynyl quinazolinone-tethered indoles
  作者：Wang Wang、Pei-Sen Zou、Li Pang、Yao Lei、Zi-Yi Huang、Nan-Ying Chen、Dong-Liang Mo、Cheng-Xue Pan、Gui-Fa Su

  DOI：10.1039/d1ob02492b

  日期：——

  An efficient gold(i)-catalyzed dearomative cyclization of N-alkynyl quinazolinone-tethered C2-substituted indoles to prepare various spiroindolenine-3,3′-pyrrolo[2,1-b]quinazolinones in good to excellent yields is reported.

  报道了一种高效的金(i)催化的脱芳香环化反应，用于制备各种螺吡咯[2,1-b]喹唑酮的衍生物，该反应中使用了N-炔基喹唑酮-拴联C2-取代吲哚，产率良好至优秀。