methyl 1,3-butadiene-2-carboxylate | 44641-19-2

• 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: methyl 1,3-butadiene-2-carboxylate
• 英文别名: methyl 2-methylene-3-butenoate；2-carbomethoxy-1,3-butadiene；2-methylene-but-3-enoic acid methyl ester；2-Methylen-but-3-ensaeure-methylester；2-methoxy-carbonyl-1,3-butadiene；2-methoxycarbonyl-1,3-butadiene；Methyl vinylacrylate；methyl 2-methylidenebut-3-enoate
• CAS: 44641-19-2
• 化学式: C₆H₈O₂
• 分子量: 112.128
• InChiKey: IZMIZHOXXIHQIY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  8
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  methyl 1,3-butadiene-2-carboxylate 生成 dimethyl mikanecate
  参考文献：
  名称：

  甲基-2-（ω-碘烷基）丙烯酸甲酯的制备及制备2-羰基甲氧基-1,3-丁二烯的简便方法

  摘要：

  α-亚甲基-γ-和δ-内酯容易与碘化三甲基甲硅烷基酯一起开环，分别生成2-（碘乙基）丙酸和2-（碘丙基）丙酸，将其甲基化得到相应的酯。用碱处理-2-（碘乙基）丙酸甲酯会生成2-羰基甲氧基-1,3-丁二烯，该二羰基甲氧基-1,3-丁二烯会发生二聚化或就地捕获。

  DOI：

  10.1016/s0040-4039(01)93823-7
• 作为产物：
  描述：

  dimethyl mikanecate 在 chromium-promoted Raney-nickel 作用下， 生成 methyl 1,3-butadiene-2-carboxylate
  参考文献：
  名称：

  Preparation of novel 2-carboalkoxy-1, 3-butadienes and polymers thereof

  摘要：

  公开号：

  US02587558A1

文献信息

• NAD(P)⁺–NAD(P)H Models. 71. A Convenient Route to the Synthesis of Juvabione
  作者：Masayuki Fujii、Tetsuo Aida、Masakuni Yoshihara、Atsuyoshi Ohno

  DOI：10.1246/bcsj.63.1255

  日期：1990.4

  Synthesis of juvabione in short steps in a high overall yield has been achieved via the chemoselective reduction with Hantzsch ester (HEH) in the presence of silica gel as a key step.

  在硅胶存在的情况下，通过化学选择性还原汉茨酯（HEH）这一关键步骤，以较短的步骤和较高的总收率合成了巨瓦二酮。
• Polythioethers bearing side groups for efficient degradation by E1cB reaction: reaction design for polymerization and main-chain scission
  作者：Ryo Kawatani、Keito Hagiwara、Anri Tanaka、Yasuhiro Kohsaka

  DOI：10.1039/d3ra03751g

  日期：——

  β-positions of ester moieties were substituted with a phenyl group. This slight modification in the polymer structure influenced the monomer structures and polymerization mechanisms. The understanding of reaction mechanisms by model reactions was required to obtain high molecular weights of polythioethers. It was clarified that the consequent additions of 1,4-diazabicyclo[2.2.2]octane (DABCO), 1,8-diazabicyclo[5

  我们之前报道过二硫醇和α-(溴甲基)丙烯酸酯串联反应的缩聚反应，由共轭取代(S N2'反应）和共轭加成（迈克尔加成）反应。所得的聚硫醚通过 E1cB 反应发生主链断裂 (MCS)，这是共轭加成的逆反应，尽管由于平衡而无法定量。在此，聚硫醚结构的修饰导致不可逆的MCS，其中酯部分的β位被苯基取代。聚合物结构的这种轻微改变影响了单体结构和聚合机制。为了获得高分子量的聚硫醚，需要通过模型反应来理解反应机理。澄清随后添加了 1,4-二氮杂双环[2.2.2]辛烷 (DABCO)、1,8-二氮杂双环[5.4.0]十一碳烯 (DBU) 和 PBu 3可以有效地获得高分子量。所得的聚硫醚通过与 DBU 的 E1cB 反应被不可逆的 MCS 分解。
• Pd-Catalyzed Sequential C–C Bond Formation and Cleavage: Evidence for an Unexpected Generation of Arylpalladium(II) Species
  作者：So Won Youn、Byung Seok Kim、Arun R. Jagdale

  DOI：10.1021/ja304616q

  日期：2012.7.18

  A Pd(II)-catalyzed reaction engaging alkenyl beta-keto esters is reported that leads to the formation of 1-naphthols and an unexpected generation of arylpalladium-(II) species. Interception of the in situ generated arylpalladium(II) species in a Mizoroki-Heck reaction, together with additional mechanistic studies, provided strong evidence in support of the first aromatization-driven beta-carbon elimination process. A single Pd catalyst served to promote a series of both C-C bond forming and cleavage events in an unprecedented manner.
• Kohler, Butler, Journal of the American Chemical Society, 1926, vol. 48, p. 1045
  作者：Kohler, Butler

  DOI：——

  日期：——
• An expedient and stereoselective route to the perhydrophenanthrene skeleton via sequential Diels-Alder reactions
  作者：Claude Spino、Jason Crawford

  DOI：10.1016/s0040-4039(00)77246-7

  日期：1994.8

  A novel and efficient stereoselective synthesis of the perhydrophenanthrene skeleton was achieved using a sequential Diels-Alder cycloaddition strategy involving enyne 10 and bis-diene 8.