N-benzyl-2-methylpent-4-enamide | 141192-61-2

• 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-benzyl-2-methylpent-4-enamide
• CAS: 141192-61-2
• 化学式: C₁₃H₁₇NO
• 分子量: 203.284
• InChiKey: DXEVFJPHGCVTRZ-UHFFFAOYSA-N

物化性质

• 沸点：
  370.6±31.0 °C(Predicted)
• 密度：
  0.985±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-benzyl-2-methylpent-4-enamide 在 Grubbs catalyst first generation 、 palladium hydroxide - carbon lithium aluminium tetrahydride 、 氢气 、 4-(4,6-二甲氧基三嗪-2-基)-4-甲基吗啉盐酸盐 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 18.0 ℃ 、101.33 kPa 条件下， 反应 142.0h， 生成 (+/-)-3-methylazacyclodecan
  参考文献：
  名称：

  海洋生物碱盐蛋白的推定结构的全合成

  摘要：

  通过明确的合成途径制备化合物1（其结构已分配给海洋天然产物盐蒜素），并进行光谱分析。导出的数据与针对天然产品报告的数据不匹配。

  DOI：

  10.1039/b105045c
• 作为产物：
  描述：

  N-benzyl-N-prop-2-enylpropanamide 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 萘烷 为溶剂， 反应 47.0h， 生成 N-benzyl-2-methylpent-4-enamide
  参考文献：
  名称：

  摘要：

  We report the synthesis of N-benzyl-N-[(E)-buta-1,3-dienyl]propanamide (6) and its corresponding O-silyl-subitituted ketene N,O-acetal 7 and their Diels-Alder reaction. Propanamide G reacted smoothly, whereas the yield obtained from 7 was low, probably due to polymerization of the dienophile induced by electron transfer. The ketene N,O-acetals 27a-g were synthesized starting from the corresponding benzamides 25a-e (Scheme 9). The ketene N,O-acetals 27a-g showed increased stabilities and underwent amino-Claisen rearrangements under thermal conditions. Using catalysts, interesting side reactions leading either to the annulated systems, rac-35-37 or to a beta -lactam rac-34 were observed.

  DOI：

  10.1002/1522-2675(20001004)83:10<2712::aid-hlca2712>3.0.co;2-d

文献信息

• Iron-Catalyzed C(sp³)–C(sp³) Coupling to Construct Quaternary Carbon Centers
  作者：Qiao Zhang、Xiang-Yu Liu、Yan-Dong Zhang、Ming-Yao Huang、Xin-Yu Zhang、Shou-Fei Zhu

  DOI：10.1021/jacs.3c14032

  日期：2024.2.28

  centers via C–C coupling protocols remains challenging. The coupling of tertiary C(sp3) with secondary or tertiary C(sp3) counterparts has been hindered by pronounced steric clashes and many side reactions. Herein, we have successfully developed a type of bisphosphine ligand iron complex-catalyzed coupling reactions of tertiary alkyl halides with secondary alkyl zinc reagents and efficiently realized the

  通过 C-C 偶联方案构建季碳中心仍然具有挑战性。叔C(sp 3 )与仲或叔C(sp 3 )对应物的偶联受到明显的空间冲突和许多副反应的阻碍。在此，我们成功开发了一种双膦配体铁配合物催化的叔卤代烷与仲烷基锌试剂的偶联反应，并高效地实现了叔C(sp 3 )和仲C(sp 3 )之间的高选择性偶联反应。初步实例为构建高位阻季碳中心提供了一种有效的方法。铁催化剂和底物的导向基团的结合使极具挑战性的转化成为可能。
• A facile α-iodination reaction of unsaturated amides
  作者：Osamu Kitagawa、Tokushi Hanano、Tatsuya Hirata、Tadashi Inoue、Takeo Taguchi

  DOI：10.1016/s0040-4039(00)91606-x

  日期：1992.3

  A novel and mild alpha-iodination of carboxamides was developed. Unsaturated amides could be converted to the alpha-iodoamides in moderate to good yields by treatment with I2 in the presence of s-collidine.
• Anti-Beckwith stereoselectivity in amidyl radical cyclisations: Bu3SnH-mediated 5-exo-trig acyl mode cyclisation of 2-substituted pent-4-enamide radicals
  作者：Andrew J. Clark、Robert P. Filik、Gerard H. Thomas、John Sherringham

  DOI：10.1016/j.tetlet.2013.05.109

  日期：2013.7

  2-Substituted amidyl radicals derived from 8a-d and 9a-d undergo acyl mode 5-exo-trig cyclisation to give 3,5-trans pyrrolidinones 11a-d and 14a-d as the major products in low diastereoselectivity (de = 9-36%). The steric nature of the nitrogen substituent attached to the amidyl radical does not have a significant effect on selectivity. The stereochemical outcome is opposite to that expected based upon applying the Beckwith rule. (C) 2013 Elsevier Ltd. All rights reserved.
• Total synthesis of the putative structure of the marine alkaloid haliclorensin
  作者：Martin G. Banwell、Andrew M. Bray、Alison J. Edwards、David J. Wong

  DOI：10.1039/b105045c

  日期：2001.11.1

  Compound 1, the structure of which has been assigned to the marine natural product haliclorensin, was prepared by an unambiguous synthetic pathway and subjected to spectroscopic analysis. The derived data do not match those reported for the natural product.

  通过明确的合成途径制备化合物1（其结构已分配给海洋天然产物盐蒜素），并进行光谱分析。导出的数据与针对天然产品报告的数据不匹配。
• ——
  作者：Klaus Neuschütz、Jean-Mary Simone、Thomas Thyrann、Reinhard Neier

  DOI：10.1002/1522-2675(20001004)83:10<2712::aid-hlca2712>3.0.co;2-d

  日期：2000.10.4

  We report the synthesis of N-benzyl-N-[(E)-buta-1,3-dienyl]propanamide (6) and its corresponding O-silyl-subitituted ketene N,O-acetal 7 and their Diels-Alder reaction. Propanamide G reacted smoothly, whereas the yield obtained from 7 was low, probably due to polymerization of the dienophile induced by electron transfer. The ketene N,O-acetals 27a-g were synthesized starting from the corresponding benzamides 25a-e (Scheme 9). The ketene N,O-acetals 27a-g showed increased stabilities and underwent amino-Claisen rearrangements under thermal conditions. Using catalysts, interesting side reactions leading either to the annulated systems, rac-35-37 or to a beta -lactam rac-34 were observed.