S-ethyl (E,2R,3S)-3-hydroxy-2-methyl-5-phenylpent-4-enethioate | 173377-13-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂醇
• 英文名称: S-ethyl (E,2R,3S)-3-hydroxy-2-methyl-5-phenylpent-4-enethioate
• CAS: 173377-13-4
• 化学式: C₁₄H₁₈O₂S
• 分子量: 250.362
• InChiKey: JOBKQDXFXLZNPW-FCSPZMLESA-N

物化性质

• 沸点：
  407.7±45.0 °C(Predicted)
• 密度：
  1.126±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  62.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  S-ethyl (E,2R,3S)-3-hydroxy-2-methyl-5-phenylpent-4-enethioate 在 三氟化硼乙醚 、 二异丁基氢化铝 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 1.5h， 生成 (2R,3R,4E)-3-Methoxy-2-methyl-5-phenyl-4-pentenal
  参考文献：
  名称：

  The first synthesis and antifungal activities of 9-methoxystrobilurin-type β-substituted β-Methoxyacrylate

  摘要：

  The first synthesis of 9-methoxystrobilurin-type beta-substituted MOAs was successfully achieved. A chiral oudemansin-type beta-substituted MOA was also synthesized utilizing Mukaiyama's asymmetric aldol reaction. Antifungal activities of the synthesized compounds against several representative fungi were examined by disk-diffusion assay. As a result, unique and superior antifungal properties of 9-methoxystrobilurin-type beta-substituted MOAs compared with those of oudemansin-type analogue were clearly revealed. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00625-x
• 作为产物：
  描述：

  (Z)-1-ethylthio-1-(trimethylsiloxy)propene 、 肉桂醛 在 tin(II) trifluoromethanesulfonate 、 (R)-1-methyl-2-(1-naphthylaminomethyl)pyrrolidine 、 二乙酸二丁基锡 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以92%的产率得到S-ethyl (E,2R,3S)-3-hydroxy-2-methyl-5-phenylpent-4-enethioate
  参考文献：
  名称：

  The first synthesis and antifungal activities of 9-methoxystrobilurin-type β-substituted β-Methoxyacrylate

  摘要：

  The first synthesis of 9-methoxystrobilurin-type beta-substituted MOAs was successfully achieved. A chiral oudemansin-type beta-substituted MOA was also synthesized utilizing Mukaiyama's asymmetric aldol reaction. Antifungal activities of the synthesized compounds against several representative fungi were examined by disk-diffusion assay. As a result, unique and superior antifungal properties of 9-methoxystrobilurin-type beta-substituted MOAs compared with those of oudemansin-type analogue were clearly revealed. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00625-x

文献信息

• Kobayashi, Shu; Horibe, Mineko, Chemistry Letters, 1995, # 11, p. 1029 - 1030
  作者：Kobayashi, Shu、Horibe, Mineko

  DOI：——

  日期：——
• The first synthesis and antifungal activities of 9-methoxystrobilurin-type β-substituted β-Methoxyacrylate
  作者：Hiromi Uchiro、Koh Nagasawa、Tomoya Kotake、Daiju Hasegawa、Aya Tomita、Susumu Kobayashi

  DOI：10.1016/s0960-894x(02)00625-x

  日期：2002.10

  The first synthesis of 9-methoxystrobilurin-type beta-substituted MOAs was successfully achieved. A chiral oudemansin-type beta-substituted MOA was also synthesized utilizing Mukaiyama's asymmetric aldol reaction. Antifungal activities of the synthesized compounds against several representative fungi were examined by disk-diffusion assay. As a result, unique and superior antifungal properties of 9-methoxystrobilurin-type beta-substituted MOAs compared with those of oudemansin-type analogue were clearly revealed. (C) 2002 Elsevier Science Ltd. All rights reserved.