甲基2-[(甲氧羰基)(甲基)氨基]丙烯酸酯 | 130291-56-4

• 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
• 中文名称: 甲基2-[(甲氧羰基)(甲基)氨基]丙烯酸酯
• 英文名称: N-(Methoxycarbonyl)-N-methyldehydroalanine methyl ester
• 英文别名: Methyl 2-[methoxycarbonyl(methyl)amino]prop-2-enoate
• CAS: 130291-56-4
• 化学式: C₇H₁₁NO₄
• 分子量: 173.169
• InChiKey: CHXSSOQJMVWSDS-UHFFFAOYSA-N

物化性质

• 沸点：
  242.7±32.0 °C(Predicted)
• 密度：
  1.130±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  甲基2-[(甲氧羰基)(甲基)氨基]丙烯酸酯 、 8-Trimethylsilanyloxy-3,4,4a,7-tetrahydro-1H-isoquinoline-2,5-dicarboxylic acid 5-methyl ester 2-phenyl ester 在 苄基三甲基氟化铵 作用下， 以 四氢呋喃 为溶剂， 以49%的产率得到8a-[2-Methoxycarbonyl-2-(methoxycarbonyl-methyl-amino)-ethyl]-8-oxo-3,4,4a,7,8,8a-hexahydro-1H-isoquinoline-2,5-dicarboxylic acid 5-methyl ester 2-phenyl ester
  参考文献：
  名称：

  Ma, Jian; Nakagawa, Masako; Torisawa, Yasuhiro, Heterocycles, 1994, vol. 38, # 7, p. 1609 - 1618

  摘要：

  DOI：
• 作为产物：
  描述：

  甲基N-(甲氧羰基)-L-丝氨酸酯 在 甲基磺酰氯 、 三乙胺 、 silver(l) oxide 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 甲基2-[(甲氧羰基)(甲基)氨基]丙烯酸酯
  参考文献：
  名称：

  Diels-Alder reactions of dihydropyridinones: synthetic entry to the manzamine A tricyclic core

  摘要：

  For the construction of the tricyclic core of manzamine A (1), the Diels-Alder reactions of some dihydropyridinones were surveyed. The N-protecting group of the dihydropyridinone played an important role in achieving a successful Diels-Alder reaction. In view of its electron-withdrawing character as well as its thermal stability, the p-toluenesulfonyl protecting group was found to be best in our synthesis. An effective method for the preparation of 3-alkyldihydropyridinones via the Michael addition to dehydroalanine derivatives has also been devised. By the utilization of a high-pressure Diels-Alder reaction of the N-tosyl-3-alkyldihydropyridinone (17) with the Danishefsky diene, a facile construction of the central pyrroloisoquinoline skeleton (21) was successfully achieved.

  DOI：

  10.1021/jo00047a031

文献信息

• Synthetic studies on manzamine a II; a novel diels-alder approach to the pyrrolo[2,3-j]isoquinoline skeleton
  作者：Yasuhiro Torisawa、Masako Nakagawa、Hitoe Arai、Ziping Lai、Tohru Hino、Tadashi Nakata、Takeshi Oishi

  DOI：10.1016/s0040-4039(00)94730-0

  日期：1990.1

  An expeditious preparation of the central pyrroloisoquinoline skeleton of manzamine A (I) was achieved via the high-pressure Diels-Alder reaction of 3-alkyl-5,6-dihydro-2-pyridinone (10) with Danishefsky diene followed by deprotection and spontaneous pyrrolidine ring clousure.

  通过3-烷基-5,6-二氢-2-吡啶酮（1 0）与Danishefsky二烯的高压Diels-Alder反应，然后进行脱保护和保护，可以快速制备曼扎明A（I）的中心吡咯并异喹啉骨架。自发性吡咯烷环闭合。
• Efficient Michael Addition Reactions of the N-Arylsulfonyl-3-phenylthiopiperidones. Synthesis of 3-Substituted Dihydropyrodinnes
  作者：Masako Nakagawa、Yasuhiro Torisawa、Toshihiro Hosaka、Kiyoshi Tanabe、Fabric Tavet、Maki Aikawa、Tohru Hino

  DOI：10.3987/com-92-s(t)117

  日期：——

  Efficient methods for the Michael addition reactions of N-arylsulfonyl-3-phenylthiopiperidones (1) with both the protected amidoacrylates (4, 9) and the simple acrylates (12) have been developed. These reactions offer an efficient route to the 3-alkyl-substituted dihydropyridinones (3, 11), the dienophiles employed in the natural product synthesis.
• TORISAWA, YASUHIRO;NAKAGAWA, MASAKO;ARAI, HITOE;LAI, ZIPING;HINO, TOHRU;N+, TETRAHEDRON LETT., 31,(1990) N2, C. 3195-3198
  作者：TORISAWA, YASUHIRO、NAKAGAWA, MASAKO、ARAI, HITOE、LAI, ZIPING、HINO, TOHRU、N+

  DOI：——

  日期：——
• Diels-Alder reactions of dihydropyridinones: synthetic entry to the manzamine A tricyclic core
  作者：Yasuhiro Torisawa、Masako Nakagawa、Toshihiro Hosaka、Kiyoshi Tanabe、Ziping Lai、Koreharu Ogata、Tadashi Nakata、Takeshi Oishi、Tohru Hino

  DOI：10.1021/jo00047a031

  日期：1992.10

  For the construction of the tricyclic core of manzamine A (1), the Diels-Alder reactions of some dihydropyridinones were surveyed. The N-protecting group of the dihydropyridinone played an important role in achieving a successful Diels-Alder reaction. In view of its electron-withdrawing character as well as its thermal stability, the p-toluenesulfonyl protecting group was found to be best in our synthesis. An effective method for the preparation of 3-alkyldihydropyridinones via the Michael addition to dehydroalanine derivatives has also been devised. By the utilization of a high-pressure Diels-Alder reaction of the N-tosyl-3-alkyldihydropyridinone (17) with the Danishefsky diene, a facile construction of the central pyrroloisoquinoline skeleton (21) was successfully achieved.
• Ma, Jian; Nakagawa, Masako; Torisawa, Yasuhiro, Heterocycles, 1994, vol. 38, # 7, p. 1609 - 1618
  作者：Ma, Jian、Nakagawa, Masako、Torisawa, Yasuhiro、Hino, Tohru

  DOI：——

  日期：——