o-methoxy-N-allylbenzamide | 66897-24-3

• 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: o-methoxy-N-allylbenzamide
• 英文别名: Benzamide, 2-methoxy-N-2-propenyl-；2-methoxy-N-prop-2-enylbenzamide
• CAS: 66897-24-3
• 化学式: C₁₁H₁₃NO₂
• mdl: MFCD01181346
• 分子量: 191.23
• InChiKey: OHTURBHELJKCQC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.181
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  o-methoxy-N-allylbenzamide 在 吡啶 、 叔丁基锂 、 溶剂黄146 、 三氟乙酸酐 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 0.33h， 生成 2-甲氧基-6-甲基苯甲腈
  参考文献：
  名称：

  Heteroatom-directed metalation. Lithiation of N-propenylbenzamides and N-propenyl-o-toluamides. Novel routes to ortho-substituted primary benzamide derivatives and N-unsubstituted isoquinolin-1(2H)-ones

  摘要：

  Reaction of N-propenylbenzamides 4 and 9, obtained by LDA-induced isomerization of the corresponding N-allylbenzamides 1, 8, and 14, with 2 equiv of sec-butyllithium or tert-butyllithium at low temperature regiospecifically generates the highly reactive N,ortho-dilithiated species (e.g., 5 and 17). These dilithio species react avidly with a wide spectrum of electrophilic reagents, including alkyl halides, giving adducts which on hydrolysis with warm 50% aqueous acetic acid are converted into ortho-substituted primary benzamides in excellent yields. Ortho-lithiation of N-propenylbenzamides is thus formally equivalent to ortho-lithiation of primary benzamides themselves. The utility of this important, previously unknown, synthetic operation is enhanced by the well-known facility with which the primary amide moiety can be transformed into other useful functional groups, as exemplified by the synthesis of 2-methoxy-6-methylbenzoic acid (12) and 2-methoxy-6-methylbenzonitrile (13) from N-propenyl-2-methoxybenzamide (9), N-Propenyl-o-toluamide (7) undergoes regiospecific dilithiation on nitrogen and on the methyl group under conditions analogous to those used for the N-propenylbenzamides. These dilithio species react with DMF or "Weinreb type" amides to give condensation products which cyclize to N-propenylisoquinolin-1(2H)-ones under midly acidic conditions. Removal of the N-propenyl moiety under more strongly acidic conditions provides N-unsubstituted isoquinolin-1(2H)-ones with high overall efficiency. This process is exemplified by the synthesis of isoquinolin-1(2H)-one (23) and its 3-n-butyl congener 26 from N-propenyl-2-methylbenzamide (7).

  DOI：

  10.1021/jo00035a030
• 作为产物：
  描述：

  邻甲氧基苯甲酸 、 丙烯胺 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 o-methoxy-N-allylbenzamide
  参考文献：
  名称：

  N-烯丙基甲酰胺的电化学氧化环化：有效合成卤代恶唑啉

  摘要：

  在此，我们报道了一种有效且可持续的N-烯丙基甲酰胺分子内电化学环化，用于合成各种卤代恶唑啉。该方法是在一个简单的未分隔的电池中进行的，使用锂卤盐作为氧化还原介质和卤素源。在室温下以中等至良好的产率构建了多种恶唑啉，包括五元和六元杂环以及碘、溴和氯甲基恶唑啉。值得注意的是，这种电化学氧化环化避免了使用外部氧化剂。

  DOI：

  10.1039/d1nj04819h

文献信息

• Efficient Tandem Process for the Catalytic Deprotection of N-Allyl Amides and Lactams in Aqueous Media: A Novel Application of the Bis(allyl)–Ruthenium(IV) Catalysts [Ru(η3:η2:η3-C12H18)Cl2] and [{Ru(η3:η3-C10H16)(μ-Cl)Cl}2]
  作者：Victorio Cadierno、José Gimeno、Noel Nebra

  DOI：10.1002/chem.200700477

  日期：2007.8.6

  highly efficient methodology for the removal of the allyl protecting group in amides and lactams has been developed by using the commercially available bis(allyl)-ruthenium(IV) catalysts [Ru(eta(3):eta(2):eta(3)-C(12)H(18))Cl(2)] (C(12)H(18)=dodeca-2,6,10-triene-1,12-diyl) and [Ru(eta(3):eta(3)-C(10)H(16))(micro-Cl)Cl}(2)] (C(10)H(16)=2,7-dimethylocta-2,6-diene-1,8-diyl). The tandem process, which

  通过使用市售的双（烯丙基）-钌（IV）催化剂[Ru（eta（3）：eta（2）： eta（3）-C（12）H（18））Cl（2）]（C（12）H（18）= dodeca-2,6,10-triene-1,12-diyl）和[Ru（ eta（3）：eta（3）-C（10）H（16））（micro-Cl）Cl}（2）]（C（10）H（16）= 2,7-二甲基辛基-2,6-二烯-1,8-二基）。串联过程发生在水性介质中并以一锅法进行，涉及烯丙基单元的C = C键的初始异构化和随后生成的烯酰胺的氧化裂解。
• Mn(OAc)₃-Mediated Hydrotrifluoromethylation of Unactivated Alkenes Using CF₃SO₂Na as the Trifluoromethyl Source
  作者：Bin Cui、Hui Sun、Yibo Xu、Lin Li、Lili Duan、Yue-Ming Li

  DOI：10.1021/acs.joc.8b00633

  日期：2018.6.1

  A simple and efficient method for hydrotrifluoromethylation of unactivated alkenes was reported. The reaction relied on the single electron oxidation of a commercially available sodium trifluoromethanesulfinate (CF3SO2Na, Langlois’ reagent) using Mn(OAc)3·2H2O as the oxidant and the subsequent addition of trifluoromethyl radical to C═C double bonds. The reaction proceeded readily under mild conditions

  报道了一种简单有效的未活化烯烃加氢三氟甲基化的方法。该反应依赖于使用Mn（OAc）3 ·2H 2 O作为氧化剂的市售三氟甲烷亚磺酸钠（CF 3 SO 2 Na，Langlois试剂）的单电子氧化，随后将三氟甲基自由基加到C═Cdouble债券。反应在温和条件下容易进行，并且对底物中的各种官能团具有良好的耐受性。通过氘化，自由基钟和TEMPO抑制实验研究了初步反应机理。
• Cockroach attraction-aggregation substance, cockroach aggregation attractant and cockroach controlling agent
  申请人：Kyoto University

  公开号：US10167269B2

  公开（公告）日：2019-01-01

  Provided is a solution for the problems associated with cockroach aggregation pheromones and cockroach aggregation attractants or cockroach controlling agents containing cockroach aggregation pheromones. In particular, provided is a compound serving as a cockroach attraction-aggregation substance, the compound being represented by general formula or a salt thereof.

  本发明提供了一种解决蟑螂聚集信息素和蟑螂聚集引诱剂或含有蟑螂聚集信息素的蟑螂控制剂相关问题的方法。特别是提供了一种用作蟑螂吸引-聚集物质的化合物，该化合物由通式或其盐表示。
• DE2744137
  申请人：——

  公开号：——

  公开（公告）日：——
• COCKROACH ATTRACTION-AGGREGATION SUBSTANCE, COCKROACH AGGREGATION ATTRACTANT AND COCKROACH CONTROLLING AGENT
  申请人：KYOTO UNIVERSITY

  公开号：US20160326129A1

  公开（公告）日：2016-11-10

  Provided is a solution for the problems associated with cockroach aggregation pheromones and cockroach aggregation attractants or cockroach controlling agents containing cockroach aggregation pheromones. In particular, provided is a compound serving as a cockroach attraction-aggregation substance, the compound being represented by general formula or a salt thereof.