5-己烯酸,3-甲基-4-羰基-,甲基酯 | 161607-24-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 酮酸及其衍生物
• 中文名称: 5-己烯酸,3-甲基-4-羰基-,甲基酯
• 英文名称: Methyl β-propenoylbutyrate
• 英文别名: Methyl 3-methyl-4-oxo-5-hexenoate；methyl 3-methyl-4-oxohex-5-enoate
• CAS: 161607-24-5
• 化学式: C₈H₁₂O₃
• 分子量: 156.181
• InChiKey: LEJCAUAJKRINHE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  11
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-己烯酸,3-甲基-4-羰基-,甲基酯 在 palladium diacetate 、 sodium hydroxide 、 potassium tert-butylate 、 三乙胺 、 三苯基膦 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 (3Z,5E)-6-{(R)-3-[1-(1,1-Dimethyl-allyloxy)-1-methyl-ethyl]-2,3-dihydro-benzo[1,4]dioxin-6-yl}-4-methoxy-3-methyl-hexa-3,5-dienoic acid methyl ester
  参考文献：
  名称：

  Total synthesis and antifungal activity of 9-methoxystrobilurin L as the originally proposed 1,4-Benzodioxan structure

  摘要：

  Total synthesis of both enantiomers of 9-methoxystrobilurin L as the originally proposed 1,4-benzodioxan structure was successfully achieved. The H-1 and C-13 NMR spectra of synthesized 9-methoxystrobilurin L were compared with those of a naturally-occurring sample. lt was strongly indicated that naturally-occurring 9-methoxystrobilurin L has not the originally reported 1,4-benzodioxan structure but a 1,5-benzodioxepin structure, the same as previously reported 9-methoxystrobilurin K. Antifungal activities of the synthesized compounds toward several typical fungi were also examined, and they were less active than 9-methoxystrobilurin K. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00561-3
• 作为产物：
  描述：

  4-methoxy-2-methyl-4-oxobutanoic acid 在 四(三苯基膦)钯 草酰氯 、 N,N-二甲基甲酰胺 作用下， 以 四氢呋喃 、 六甲基磷酰三胺 为溶剂， 反应 2.0h， 生成 5-己烯酸,3-甲基-4-羰基-,甲基酯
  参考文献：
  名称：

  Concise total synthesis of 9-methoxystrobilurin A

  摘要：

  Total synthesis of a potent antifungal and cytostatic 9-methoxystrobilurin A was achieved by developing a concise and general route to beta-methoxy acrylate. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)00559-1

文献信息

• Asymmetric total synthesis of 9-methoxystrobilurin K
  作者：Hiromi Uchiro、Koh Nagasawa、Yasuyuki Aiba、Tomoya Kotake、Daiju Hasegawa、Susumu Kobayashi

  DOI：10.1016/s0040-4039(01)00812-7

  日期：2001.7

  Asymmetric total synthesis of a potent antifungal and cytostatic 9-methoxystrobilurin K was achieved by developing a convergent and versatile synthetic route.

  有效的抗真菌和抑制细胞生长作用的9-甲氧基金刚霉素K的不对称全合成是通过开发一种收敛的多功能合成路线实现的。
• Remarkable influence of the aromatic substructure in 9-methoxystrobilurin derivatives on their antifungal activity
  作者：Hiromi Uchiro、Koh Nagasawa、Tomohiro Sawa、Daiju Hasegawa、Tomoya Kotake、Yoshitsugu Sugiura、Susumu Kobayashi、Kazuhiko Otoguro、Satoshi Ōmura

  DOI：10.1016/s0960-894x(02)00558-9

  日期：2002.10

  9-Methoxystrobilurin-type beta-methoxyacrylate antibiotics (MOSBs) having various aromatic substructures were synthesized. The antifungal activity of the synthesized MOSBs against pathogenic and non-pathogenic fungi was examined, and the obtained results revealed that the antifungal activity of MOSBs was highly dependent on the aromatic substructures. However, no significant correlation was observed between cytotoxicity against human fibroblasts-like cell line and their structural properties. In addition, our results suggested that the strong growth-inhibitory activity of 9-methoxystrobilurin K against human-derived cell lines should be related to its hindered ether-type substructure. (C) 2002 Elsevier Science Ltd. All rights reserved.
• A Novel Heterocycle-Stabilized Homoenolate Anion and Its Applications in the Syntheses of .beta.-Propenoylcarboxylic Esters, Cyclopropanecarboxylic Esters, 1-Vinyl-1-ethoxy Epoxides, and .gamma.-Lactones
  作者：Alan R. Katritzky、Jinlong Jiang

  DOI：10.1021/jo00106a003

  日期：1995.1
• N-(.alpha.-Ethoxyallyl)benzotriazole: A Novel Propenoyl Anion Synthon Route to Vinyl Ketones
  作者：Alan R. Katritzky、Guifen Zhang、Jinlong Jiang

  DOI：10.1021/jo00128a035

  日期：1995.11

  Lithiation with butyllithium of N-(alpha-ethoxyallyl)benzotriazole (2) (readily prepared in quantitative yield on a large scale from benzotriazole and acrolein diethyl acetal (9)) followed by reaction of lithio derivative 14 with halides, alpha,beta-unsaturated esters, alpha,beta-unsaturated ketones, and aldehydes gave exclusively alpha-alkylation adducts. These adducts are hydrolyzed under extremely mild conditions, enabling convenient syntheses of vinyl ketones 16 and functionalized vinyl ketones 21, 22, 24, and 27.
• Katritzky Alan R., Jiang Jinlong, J. Org. Chem, 60 (1995) N 1, S 6-7
  作者：Katritzky Alan R., Jiang Jinlong

  DOI：——

  日期：——