methyl (E)-6-(3,4-dimethoxyphenyl)-3-methyl-4-oxohex-5-enoate | 287484-99-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 英文名称: methyl (E)-6-(3,4-dimethoxyphenyl)-3-methyl-4-oxohex-5-enoate
• CAS: 287484-99-5
• 化学式: C₁₆H₂₀O₅
• 分子量: 292.332
• InChiKey: VFYBSNVYGPCQHL-FNORWQNLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  21
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl (E)-6-(3,4-dimethoxyphenyl)-3-methyl-4-oxohex-5-enoate 在 sodium hydride 、 potassium carbonate 、 对甲苯磺酸 、 硫酸二甲酯 作用下， 以 甲醇 、 丙酮 、 苯 为溶剂， 反应 6.0h， 生成 methyl (2Z,3E,5E)-6-(3,4-dimethoxyphenyl)-4-methoxy-2-(methoxymethylidene)-3-methylhexa-3,5-dienoate
  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
• 作为产物：
  描述：

  3-甲氧基羰基-2-甲基-丙酸氯 在 palladium diacetate 、 四(三苯基膦)钯 三乙胺 、 三苯基膦 作用下， 以 六甲基磷酰三胺 为溶剂， 反应 19.0h， 生成 methyl (E)-6-(3,4-dimethoxyphenyl)-3-methyl-4-oxohex-5-enoate
  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

• 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.