3-<2-(1(E)-pentenyl)phenyl>-2(E)-propenoic acid ethyl ester | 147932-32-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: 3-<2-(1(E)-pentenyl)phenyl>-2(E)-propenoic acid ethyl ester
• 英文别名: ethyl (E)-3-[2-[(E)-pent-1-enyl]phenyl]prop-2-enoate
• CAS: 147932-32-9
• 化学式: C₁₆H₂₀O₂
• 分子量: 244.334
• InChiKey: FGFIVPMMOXPHKR-UXKPLKHMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 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：

  3-<2-(1(E)-pentenyl)phenyl>-2(E)-propenoic acid ethyl ester 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以140 mg的产率得到3-<2-(1(E)-pentenyl)phenyl>-2(E)-propenoic acid
  参考文献：
  名称：

  Structure of WS9326A, a novel tachykinin antagonist from a Streptomyces

  摘要：

  A novel tachykinin antagonist WS9326A was isolated from Streptomyces violaceoniger no. 9326. It is an acylated macrocyclic heptapeptide lactone consisting Of L-Thr, (E)-dehydro-N-methyltyrosine ((E)-DELTAMeTYr), L-Leu, D-Phe, L-alloThr, L-Asn, L-Ser, and 3-[2-(1(Z)-pentenyl)phenyl]-2(E)-propenoic acid. Its structure, including absolute stereochemistry, was unequivocally determined as 1 on the basis of chemical and spectroscopic evidence. The spectroscopic investigations were carried out mainly with 2, the triacetyl derivative of WS9326A. This is the first example of a tachykinin antagonist isolated from a natural source.

  DOI：

  10.1021/jo00053a032
• 作为产物：
  描述：

  邻苯二甲醛 在 正丁基锂 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 生成 3-<2-(1(E)-pentenyl)phenyl>-2(E)-propenoic acid ethyl ester
  参考文献：
  名称：

  Structure of WS9326A, a novel tachykinin antagonist from a Streptomyces

  摘要：

  A novel tachykinin antagonist WS9326A was isolated from Streptomyces violaceoniger no. 9326. It is an acylated macrocyclic heptapeptide lactone consisting Of L-Thr, (E)-dehydro-N-methyltyrosine ((E)-DELTAMeTYr), L-Leu, D-Phe, L-alloThr, L-Asn, L-Ser, and 3-[2-(1(Z)-pentenyl)phenyl]-2(E)-propenoic acid. Its structure, including absolute stereochemistry, was unequivocally determined as 1 on the basis of chemical and spectroscopic evidence. The spectroscopic investigations were carried out mainly with 2, the triacetyl derivative of WS9326A. This is the first example of a tachykinin antagonist isolated from a natural source.

  DOI：

  10.1021/jo00053a032

文献信息

• Structure of WS9326A, a novel tachykinin antagonist from a Streptomyces
  作者：Nobuharu Shigematsu、Kenichi Hayashi、Natsuko Kayakiri、Shigehiro Takase、Masashi Hashimoto、Hirokazu Tanaka

  DOI：10.1021/jo00053a032

  日期：1993.1

  A novel tachykinin antagonist WS9326A was isolated from Streptomyces violaceoniger no. 9326. It is an acylated macrocyclic heptapeptide lactone consisting Of L-Thr, (E)-dehydro-N-methyltyrosine ((E)-DELTAMeTYr), L-Leu, D-Phe, L-alloThr, L-Asn, L-Ser, and 3-[2-(1(Z)-pentenyl)phenyl]-2(E)-propenoic acid. Its structure, including absolute stereochemistry, was unequivocally determined as 1 on the basis of chemical and spectroscopic evidence. The spectroscopic investigations were carried out mainly with 2, the triacetyl derivative of WS9326A. This is the first example of a tachykinin antagonist isolated from a natural source.