(E)-N-benzyl-2-methylbut-2-enamide | 83375-42-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (E)-N-benzyl-2-methylbut-2-enamide
• CAS: 83375-42-2
• 化学式: C₁₂H₁₅NO
• 分子量: 189.257
• InChiKey: NIYNXMANQCLVBT-XCVCLJGOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 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：

  (E)-N-benzyl-2-methylbut-2-enamide 在 氢氧化钾 、 四丁基溴化铵 、 镍 作用下， 以 丙酮 为溶剂， 反应 18.5h， 生成 (+/-)-1-benzyl-3β,4β-dimethylazetidin-2-one
  参考文献：
  名称：

  Ihara, Masataka; Fukumoto, Keiichiro, Heterocycles, 1982, vol. 19, # 8, p. 1435 - 1438

  摘要：

  DOI：
• 作为产物：
  描述：

  惕格酸 、 苄胺 在 4-(2-(1,3-dioxa-3a1,8,10-triaza-2,3a,14b-triboradibenzo[fg,op]tetracen-2-yl)phenyl)benzo[c]pyrimido[4,5-e][1,2]azaborinin-6(5H)-ol 作用下， 以 氟苯 为溶剂， 反应 16.0h， 以90%的产率得到(E)-N-benzyl-2-methylbut-2-enamide
  参考文献：
  名称：

  所有非碳B3NO2外来杂环：合成，动力学和催化

  摘要：

  B 3 NO 2六元杂环（1,3-二氧杂-5-氮杂-2,4,6-三硼烷= DATB），由三种不同的非碳2期元素组成，最近被证明是羧酸脱水缩合的强大催化剂酸和胺。然而，繁琐的DATB合成大大降低了其作为催化剂的用途，因此，实际上仍未探索环系统的固有化学性质。在此公开了一种通用且简便的合成策略，该策略利用含嘧啶的支架可靠地安装硼原子，从而以模块化的方式由廉价材料制成了一系列Pym-DATB。可溶性Pym‐DATB衍生物的鉴定可用于研究B 3 NO 2的动力学性质环系统，根据介质的不同，显示出不同的开环和开环行为。易于获取的Pym‐DATB证明了其作为脱水酰胺化的有效催化剂的实用性，具有广泛的底物范围和官能团耐受性，为试剂驱动的酰胺化提供了一种通用且实用的催化替代方法。

  DOI：

  10.1002/chem.201900715

文献信息

• Less Is More: N(BOH)₂ Configuration Exhibits Higher Reactivity than the B₃NO₂ Heterocycle in Catalytic Dehydrative Amide Formation
  作者：Christopher R. Opie、Hidetoshi Noda、Masakatsu Shibasaki、Naoya Kumagai

  DOI：10.1021/acs.orglett.2c04382

  日期：2023.2.3

  Diboron substructures have emerged as a promising scaffold for the catalytic dehydrative amidation of carboxylic acids and amines. This Letter describes the design, synthesis, and evaluation of the first isolable N(BOH)2 compound as an amidation catalyst. The new catalyst outperforms the previously reported B3NO2 heterocycle catalyst, with respect to turnover frequency, albeit the former gradually

  二硼子结构已成为羧酸和胺的催化脱水酰胺化的有前途的支架。这封信描述了第一个可分离的 N(BOH) 2化合物作为酰胺化催化剂的设计、合成和评估。就周转频率而言，新催化剂优于先前报道的 B 3 NO 2杂环催化剂，尽管前者在暴露于胺时会逐渐分解。这项工作为设计更好的直接酰胺化催化剂开辟了一条途径。
• Synthesis of γ-Lactams from Acrylamides by Single-Carbon Atom Doping Annulation
  作者：Hayato Fujimoto、Bunta Nakayasu、Mamoru Tobisu

  DOI：10.1021/jacs.3c07052

  日期：2023.9.13

  A protocol for single-carbon atom doping annulation is reported, which enables the conversion of acrylamides into homologated γ-lactams through the cleavage of two σ-bonds and the formation of four new σ-bonds at the single carbon center. The key strategy is the use of N-heterocyclic carbenes as an atomic carbon equivalent by acting as carbon atom donors through the loss of a 1,2-diimine moiety. Experimental

  报道了单碳原子掺杂环化的方案，该方案能够通过两个σ键的裂解并在单碳中心形成四个新的σ键，将丙烯酰胺转化为同系的γ-内酰胺。关键策略是通过失去 1,2-二亚胺部分而充当碳原子供体，从而使用N-杂环卡宾作为原子碳当量。实验和计算研究表明，该反应通过螺环中间体进行，然后通过质子转移分解N-杂环卡宾骨架。
• Photochemical isomerization of N-monosubstituted .alpha.,.beta.-unsaturated thioamides to iminothietanes
  作者：Masami Sakamoto、Tsutomu Ishida、Tsutomu Fujita、Shoji Watanabe

  DOI：10.1021/jo00034a040

  日期：1992.4

  Photochemical isomerization of thiomethacryl-, thiotiglyl-, and thiocrotonamides gives iminothietanes, N-(2-thietanylidene)amines, in good yields. The iminothietanes reverted quantitatively to the starting materials on heating. Use of Michler's ketone or thioxanthone as sensitizers indicates that the photoelectric cyclization proceeds from the triplet excited state. Irradiation of N-benzylthiocinnamamide does not give an iminothietane, but only cis-trans isomerization that reached the photostationary state at cis/trans = 1.7.
• Solid State Photochemical Reaction of <i>N</i>-(α,β-Unsaturated carbonyl)benzoylformamides
  作者：Masami Sakamoto、Masaki Takahashi、Tsutomu Fujita、Shoji Watanabe、Takehiko Nishio、Ikuo Iida、Hiromu Aoyama

  DOI：10.1021/jo9704974

  日期：1997.9.1

  Photochemical reactions of various N-(alpha,beta-unsaturated carbonyl)benzoylfomamides both in solution and in a solid state were investigated. Under homogeneous conditions, all acyclic imides underwent photochemical 2 + 2 cycloaddition that resulted in the production of bicyclic oxetanes. N-Isopropyl- and N-benzyl-N-tigloylbenzoylformamides crystallized in a chiral space group, and the photolysis in the solid state yielded corresponding optic ally-active oxetanes. N-Tigloylbenzoylformanilide underwent cis-trans isomerization to yield a photostationary state (cis/trans = 1.3). Solid state oxetane formation of N-benzyl- and N-(o-tolyl)- and N-(2,6-xylpl)-N-tigloylbenzoylformamides progressed via the crystal-to-crystal pathway which was followed by X-ray powder diffraction, N-Benzyl-N-methacryloylbenzoylformamide crystallized in a chiral space group, and the solid state reaction led to an optically active beta-lactam via topochemically-controlled hydrogen abstraction by the alkenyl carbon atom. Photolysis of N-isopropyl-N-methacryloylbenzoylformamide in the solid state led to both oxetane formation and a transformation to azetidine-2,4-dione involving a 1,5-benzoyl shift.
• Synthesis of .beta.-lactam antibiotics by the sulfeno-cycloamination
  作者：Masataka Ihara、Yo Haga、Mariko Yonekura、Tatsushi Ohsawa、Keiichiro Fukumoto、Tetsuii Kametani

  DOI：10.1021/ja00363a023

  日期：1983.11