Methyl (E)/(Z)-3-Bromo-2-formylaminocinnamate | 1265278-17-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: Methyl (E)/(Z)-3-Bromo-2-formylaminocinnamate
• 英文别名: (Z)-methyl β-bromo-α-formylaminocinnamate；(Z)-Methyl 3-bromo-2-(formylamino)-3-phenylacrylate；methyl 3-bromo-2-formamido-3-phenylprop-2-enoate
• CAS: 1265278-17-8
• 化学式: C₁₁H₁₀BrNO₃
• 分子量: 284.109
• InChiKey: CBLWNDXTCPJZBH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.67
• 重原子数：
  16.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  55.4
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  Methyl (E)/(Z)-3-Bromo-2-formylaminocinnamate 在 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 以76%的产率得到4-methoxycarbonyl-2-oxo-5-phenylimidazoline
  参考文献：
  名称：

  β-官能化的α，β-脱氢氨基酸衍生物的合成

  摘要：

  通过加成消除途径合成了β-官能化的α，β-不饱和氨基酸。通过将异氰基乙酸甲酯（1）与醛缩合，然后溴化与硫醇反应制得的β-溴-α-甲酰基氨基丙烯酸甲酯（3a-e）反应，得到β-烷硫基-α，β-不饱和氨基酸衍生物（ 6a-f）。（3a）与叠氮化钠的反应导致形成2-氧代咪唑啉衍生物（4）。另一方面，通过由（3a和3d），分别用苄醇和苄胺，然后进行酸性水合。

  DOI：

  10.1016/s0040-4020(01)86052-x
• 作为产物：
  描述：

  (Z)-2-Formylamino-3-phenyl-acrylic acid methyl ester 在 N-溴代丁二酰亚胺(NBS) 作用下， 生成 Methyl (E)/(Z)-3-Bromo-2-formylaminocinnamate
  参考文献：
  名称：

  2,4,5-Trisubstituted Thiazole Building Blocks by a Novel Multi-Component Reaction

  摘要：

  描述了一种新的多组分反应（MCR），该反应涉及氧组分、初级胺、硫羧酸和3溴-2-异氰基丙烯酸酯，生成2,4,5-三取代噻唑的构建块。

  DOI：

  10.1055/s-2004-836035

文献信息

• (Z)-selective β-bromination ofN-formyl-α, β-dehydroamino acid esters
  作者：Masaki Yamada、Kazuya Nakao、Toshio Fukui、Ken-ichi Nunami

  DOI：10.1016/0040-4020(96)00209-8

  日期：1996.4

  Stereoselective β-bromination ofN-formyl-α, β-dehydroamino acid esters5 was investigated. A reaction of5 with NBS affordedα-bromo-N-formylimines10 which successively isomerized to giveβ-bromo-N-formyl-α, β-dehydroamino acid esters4. The migration of the double bond of the intermediates10 with bulky substituents at the β-position resulted in highly stereoselective formation of(Z)-4, while that of the

  研究了N-甲酰基-α，β-脱氢氨基酸酯5的立体选择性β-溴化。5与NBS的反应得到α-溴-N-甲酰亚胺10，其连续异构化以得到β-溴-N-甲酰-α，β-脱氢氨基酸酯4。具有在β位的大取代基的中间体10的双键的迁移导致（Z）-4的高度立体选择性的形成，而具有大的取代基的底物的双键的非立体选择性地进行。在使用AM1进行半经验计算的基础上，提出了立体选择性溴化的机理。
• A Facile Synthesis of Methyl 1,5-Disubstituted Imidazole-4-carboxylates
  作者：Kiwamu Hiramatsu、Ken-ichi Nunami、Kimiaki Hayashi、Kazuo Matsumoto

  DOI：10.1055/s-1990-27013

  日期：——

  Various methyl 1,5-disubstituted imidazole-4-carboxylates are synthesized by the reaction of methyl 3-bromo-2-isocyanoacrylates with a variety of primary amines in the presence of triethylamine.

  在三乙胺存在下，3-溴-2-异氰基丙烯酸甲酯与多种伯胺发生反应，合成出各种 1,5-二取代咪唑-4-羧酸甲酯。
• Screening Multicomponent Reactions for X-Linked Inhibitor of Apoptosis-Baculoviral Inhibitor of Apoptosis Protein Repeats Domain Binder
  作者：Ilaria Monfardini、Jui-Wen Huang、Barbara Beck、Jason F. Cellitti、Maurizio Pellecchia、Alexander Dömling

  DOI：10.1021/jm101341m

  日期：2011.2.10

  We report a second example of a general reaction screening approach to discover low molecular weight inhibitors of protein protein interactions. On the basis of the known pharmacophore model of SMAC mimetics, we predicted several inhibitors based on four different multicomponent reactions. The predicted inhibitors were subsequently synthesized, tested, and found to bind to the antiapoptotic protein X-linked inhibitor of apoptosis protein (XIAP) and showed cellular activity. Also the compounds are currently not highly potent. They could form a starting point for future medicinal chemistry optimization.
• A Novel Synthesis of Methyl 1,5-Disubstituted Imidazole-4-carboxylates Using 3-Bromo-2-isocyanoacrylates (BICA)
  作者：Ken-ichi Nunami、Masaki Yamada、Toshio Fukui、Kazuo Matsumoto

  DOI：10.1021/jo00104a018

  日期：1994.12

  Methyl 1,5-disubstituted imidazole-4-carboxylates 1 were synthesised using methyl 3-substituted 3-bromo-2-isocyanoacrylates 3 (BICA), and the reaction mechanism was elucidated. Reactions of 3, which were prepared by bromination of 3-substituted 2-(formylamino)acrylates 6 followed by dehydration of the formylamino group, with a variety of primary amines gave imidazoles 1 in good overall yields. A mechanistic study suggested a Michael reaction of an amine with 3 followed by p-elimination of hydrogen bromide exclusively afforded (E)-N,3-disubstituted 3-amino-2-isocyanoacrylates 2. Geometric isomerization to (Z)-2 with a base and subsequent cyclization gave imidazoles 1.
• A novel synthesis of methyl 5-substituted thiazole-4-carboxylates using 3-bromo-2-isocyanoacrylates (BICA)
  作者：Masaki Yamada、Toshio Fukui、Ken-ichi Nunami

  DOI：10.1016/0040-4039(94)02186-f

  日期：1995.1

  A novel synthetic method for methyl 5-substituted thiazole-4-carboxylates (5) by the reaction of methyl 3-substituted 3-bromo-2-isocyanoacrylates(BICA)(1) with hydrogen sulfide in the presence of triethylamine in N,N-dimethylformamide was explored, and the reaction mechanism was elucidated.