N-(Phenylmethyl)-N-2-propenylformamide | 863313-50-2

• 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: N-(Phenylmethyl)-N-2-propenylformamide
• 英文别名: N-allyl-N-benzylformamide；N-benzyl-N-prop-2-enylformamide
• CAS: 863313-50-2
• 化学式: C₁₁H₁₃NO
• 分子量: 175.23
• InChiKey: SEGRNWZHGBNYCI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  ethyl diazo(triethylsilyl)acetate 、 N-(Phenylmethyl)-N-2-propenylformamide 在 dirhodium tetraacetate 作用下， 以 苯 为溶剂， 反应 1.5h， 以85%的产率得到ethyl (Z)-3-(N-allyl-N-benzylamino)-2-(triethylsilyloxy)acrylate
  参考文献：
  名称：

  铑（II）催化的叔甲酰胺与甲硅烷基化的重氮酯的烯化反应合成乙烯基氨基甲酸酯。

  摘要：

  在铑（II）催化剂存在下用甲硅烷基化的重氮酯处理叔甲酰胺导致高产率地形成3-氨基-2-甲硅烷氧基丙烯酸酯。如果使用非甲硅烷基化的重氮化合物，则未观察到烯化。[反应：看文字]

  DOI：

  10.1021/ol0510872
• 作为产物：
  描述：

  N-烯丙基苄胺 在 sodium hydroxide 、 sodium hydride 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 N-(Phenylmethyl)-N-2-propenylformamide
  参考文献：
  名称：

  Intramolecular Diels-Alder Reactions. 5. Approaches to the Pyrrolo[3,4-c]carbazole and Pyrido[4,3-c]carbazole Systems1

  摘要：

  Two methods for the preparation of indole-2,3-quinodimethanes are reported. Treatment of 1,2-dimethyl-alpha-oxo-N-(phenylmethyl)-N-2-propenyl-1H-indole-3-acetamide (3) with sodium bis(trimethylsilyl)amide in refluxing THF gave 2-(phenylmethyl)-10c-hydroxy-6-methyl-3,3a,4,5,6,10c-hexahydropyrrolo[3,4-c]-carbazol-1(2H)-one (5) in 18% yield by intramolecular Diels-Alder reaction of the intermediate enolate 4. LiBH4-reduction of amide 3 and thermolysis of the resulting alpha-hydroxyamide 8 at 190 degrees C gave a 63:37 mixture of the cis and trans isomers of 2-(phenylmethyl)-6-methyl-3,3a,4,5,6,10c-hexahydropyrrolo[3,4-c]carbaxol-1(2H)-one (9a and 9b) in 64% yield. The corresponding N-3-butenylamide 10 at 205 degrees C led to a 67:33 mixture of cis- and trans-7-methyl-2,3,4,4a,5,6,7,11c-octahydro-2-(phenylmethyl)-1H-pyrido[4,3-c]carbazol-1-one (11a and 11b) in 53% yield. Thermolysis of 1,2-dimethyl-alpha-hydroxy-N-(phenylmethyl)-N-2-propynyl-1H-indole-3-acetamide (15) gave an equimolar mixture of lactam 9a and the aromatized product, 3,6-dihydro-6-methyl-2-(phenylmethyl)pyrrolo[3,4-c]carbazol-1(2H)-one (17) in 80% yield by disproportionation of the intermediate lactam 16. Reaction of 1,2-dimethyl-1H-indole-3-carboxaldehyde with methyl acrylate and sodium bis(trimethylsilyl)amide produced methyl 1,2-dihydro-9-methyl-9H-carbazole-3-carboxylate (20) in 26% yield, most likely by a sequence of Michael addition to the enolate of the aldehyde and intramolecular aldol condensation.

  DOI：

  10.1021/jo00119a046

文献信息

• [EN] 2-SULFANYL-BENZOIMIDAZOL-1-YL-ACETIC ACID DERIVATIVES AS CRTH2 ANTAGONISTS<br/>[FR] DERIVES DE L'ACIDE 2-SULFANYL-BENZOIMIDAZOL-1-YL-ACETIQUE EN TANT QU'ANTAGONISTES DE CRTH2
  申请人：ACTELION PHARMACEUTICALS LTD

  公开号：WO2006021418A1

  公开（公告）日：2006-03-02

  The invention relates to 2-sulfanyl-benzoimidazol-1-yl-acetic acid derivatives and their use as potent 'chemoattractant receptor-homologous molecule expressed on Th2 cells' antagonists in the treatment of prostaglandin mediated diseases, to pharmaceutical compositions containing these derivatives and to processes for their preparation.

  这项发明涉及2-硫代基苯并咪唑-1-基乙酸衍生物及其在治疗前列腺素介导的疾病中作为强效“趋化受体同源分子在Th2细胞上表达”的拮抗剂的用途，涉及含有这些衍生物的药物组合物以及其制备方法。
• Effective Formylation of Amines with Carbon Dioxide and Diphenylsilane Catalyzed by Chelating bis(<i>tz</i>NHC) Rhodium Complexes
  作者：Thanh V. Q. Nguyen、Woo-Jin Yoo、Shū Kobayashi

  DOI：10.1002/anie.201504072

  日期：2015.8.3

  (NHC=N‐heterocyclic carbene) have been synthesized and applied to the reductive formylation of amines using CO2 and Ph2SiH2. A rhodium‐based bis(tzNHC) complex (tz=1,2,3‐triazol‐5‐ylidene) was identified to be highly effective at a low catalyst loading and ambient temperature, and a wide substrate scope, including amines with reducible functional groups, were compatible.

  使用CO 2和氢硅烷对胺进行还原甲酰化是将CO 2引入有价值的有机化合物中的一种有吸引力的方法。然而，先前的系统需要高催化剂负载量或高温才能达到高效率，并且底物范围主要限于简单的胺。为了解决这些问题，已经合成了一系列烷基桥连的螯合双（NHC）铑配合物（NHC = N-杂环卡宾），并将其用于使用CO 2和Ph 2 SiH 2还原胺的甲酰化反应。铑基双（tz NHC）络合物（tz1,2,3-三唑-5亚基）在较低的催化剂负载量和环境温度下被认为是高效的，并且兼容广泛的底物范围，包括具有可还原官能团的胺。
• Generation and Cyclization of Unsaturated Carbamoyl Radicals Derived from <i>S</i>-4-Pentynyl Carbamothioates under Tin-Free Conditions
  作者：Luisa Benati、Giorgio Bencivenni、Rino Leardini、Matteo Minozzi、Daniele Nanni、Rosanna Scialpi、Piero Spagnolo、Giuseppe Zanardi

  DOI：10.1021/jo0602064

  日期：2006.4.1

  The radical reaction of benzenethiol with S-4-pentynyl carbamothioates provides a valuable protocol for the tin-free generation of carbamoyl radicals, which arise from intramolecular substitution at sulfur by the initial sulfanylvinyl radicals. This procedure can be usefully employed to achieve N-benzylcarbamoyl radical 5-exo and 4-exo cyclizations leading, respectively, to pyrrolidinones and azetidinones

  苯硫酚与S -4-戊炔基氨基甲酸酯的自由基反应为无锡生成氨基甲酰基自由基提供了有价值的方案，该氨基甲酰基自由基是由硫在分子内被初始的硫烷基乙烯基自由基取代而产生的。该方法可以有效地用于实现分别导致吡咯烷酮和氮杂环丁烷酮的N-苄基氨基甲酰基自由基5-exo和4-exo环化，尽管对于后者而言，其效用较小。提出了新的证据，N-甲苯磺酰基取代的氨基甲酰基自由基表现出通过β-消除甲苯磺酰基自由基产生相应的异氰酸酯的独特趋势。
• Formylation of amines catalysed by protic ionic liquids under solvent-free condition
  作者：Swapan Majumdar、Jhinuk De、Jewel Hossain、Ajoy Basak

  DOI：10.1016/j.tetlet.2012.11.017

  日期：2013.1

  A fast, efficient and simple route for the N-formylation of amines has been developed by treating amines with 85% formic acid at 70 °C in the presence of 5 mol % of protic ionic liquid as catalyst under solvent-free condition. This method provides a green and much improved protocol over the existing methods.

  通过在无溶剂条件下，在5 mol％的质子离子液体作为催化剂的情况下，在70°C下用85％的甲酸处理胺，从而开发出一种快速，高效且简单的胺N-甲酰基化方法。与现有方法相比，该方法提供了绿色且经过改进的协议。
• 2-Sulfanyl-Benzoimidazol-1-Yl-Acetic Acid Derivatives as Crth2 Antagonists
  申请人：Fretz Heinz

  公开号：US20080108638A1

  公开（公告）日：2008-05-08

  The invention relates to 2-sulfanyl-benzoimidazol-1-yl-acetic acid derivatives and their use as potent “chemoattractant receptor-homologous molecule expressed on Th2 cells” antagonists in the treatment of prostaglandin mediated diseases, to pharmaceutical compositions containing these derivatives and to processes for their preparation.

  本发明涉及2-硫基苯并咪唑-1-基乙酸衍生物及其在治疗前列腺素介导的疾病中作为有效的“趋化因子受体同源分子表达在Th2细胞”拮抗剂的使用，以及含有这些衍生物的制药组合物和其制备过程。