2,5-二氢-3-异丙基-2,5-二氧代-1H-吡咯-1-丙酸 | 1175521-35-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 中文名称: 2,5-二氢-3-异丙基-2,5-二氧代-1H-吡咯-1-丙酸
• 英文名称: farinomalein A
• 英文别名: farinomalein；3-(2,5-dioxo-3-propan-2-ylpyrrol-1-yl)propanoic acid
• CAS: 1175521-35-3
• 化学式: C₁₀H₁₃NO₄
• 分子量: 211.218
• InChiKey: UWAZSQUZHSRNTR-UHFFFAOYSA-N

物化性质

• 密度：
  1.281

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  74.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,5-二氢-3-异丙基-2,5-二氧代-1H-吡咯-1-丙酸 在 4-二甲氨基吡啶 、 溶剂黄146 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 3.0h， 生成 (S)-farinomalein D
  参考文献：
  名称：

  Synthesis of natural maleimides farinomaleins C–E and evaluation of their antifungal activity

  摘要：

  A practical and convenient synthesis of naturally occurring farinomaleins C-E was achieved starting from readily available ethyl 3-methyl-2-oxobutyrate and triethyl phosphonoacetate. The key steps of the sequence included a Horner-Wadsworth-Emmons condensation to obtain the precursor farinomalein A and coupling with suitable alcohols to install the chain. The synthesis of farinomalein D has been achieved starting from (R)-isopropylideneglycerol on the basis of which the S configuration was assigned to the natural compound. The antifungal activity of the synthesized compounds was evaluated against Cladosporium cladosporioides. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.05.023
• 作为产物：
  描述：

  3-甲基-2-氧代丁酰乙酯 在 sodium hydride 、 溶剂黄146 、 三氟乙酸酐 、 lithium hydroxide 作用下， 以 四氢呋喃 、 水 、 mineral oil 为溶剂， 反应 10.58h， 生成 2,5-二氢-3-异丙基-2,5-二氧代-1H-吡咯-1-丙酸
  参考文献：
  名称：

  Farinomalein 及其类似物的改进合成

  摘要：

  摘要描述了一种实用且方便的杀真菌天然化合物粉状马来酸的合成方法，该合成方法以现成的 3-甲基-2-氧代丁酸乙酯和膦酰基乙酸三乙酯为起始原料，关键步骤为霍纳-沃兹沃思-埃蒙斯缩合反应。补充材料可用于本文。转至出版商的 Synthetic Communications® 在线版以查看免费的补充文件。图形概要

  DOI：

  10.1080/00397911.2011.640969

文献信息

• Plausible Reaction Path for Haval-Argade Contrathermodynamic Rearrangement in Synthesis of Farinomalein
  作者：Narayan P. Firke、Anil G. Markandeya、Rajendra S. Konde Deshmukh、Shirish S. Pingale

  DOI：10.14233/ajchem.2018.21142

  日期：——

  This work reports, the plausible reaction path in context of the farinomalein (1) and isofarinomalein (2) synthesized via Stobbe condensation and Haval-Argade Contrathermodynamic Rearrangement.

  这篇工作报告了通过斯托布缩合和哈瓦尔-阿加德反热力学重排合成的法尼马林（1）和异法尼马林（2）的合理反应路径。
• Synthesis of farinomalein
  作者：William H. Miles、Ming Yan

  DOI：10.1016/j.tetlet.2010.01.083

  日期：2010.3

  Farinomalein, a recently isolated maleimide from Paecilomyces farinosus, was synthesized in two steps from a readily available gamma-hydroxybutenolide. (C) 2010 Elsevier Ltd. All rights reserved.
• Farinomalein, a Maleimide-Bearing Compound from the Entomopathogenic Fungus <i>Paecilomyces farinosus</i>
  作者：Sastia P. Putri、Hiroshi Kinoshita、Fumio Ihara、Yasuhiro Igarashi、Takuya Nihira

  DOI：10.1021/np9002806

  日期：2009.8.28

  A new maleimide-bearing compound, farinomalein (1), was isolated from the entomopathogenic fungus Paecilomyces farinosus HF599. The structure was determined on the basis of spectroscopic analyses and chemical conversion. Compound 1 showed potent activity (5 mu g/disk) against the plant pathogenic Phytophthora sojae P6497.
• Synthesis of natural maleimides farinomaleins C–E and evaluation of their antifungal activity
  作者：Santosh Lahore、Sachin T. Aiwale、Paola Sardi、Sabrina Dallavalle

  DOI：10.1016/j.tetlet.2014.05.023

  日期：2014.7

  A practical and convenient synthesis of naturally occurring farinomaleins C-E was achieved starting from readily available ethyl 3-methyl-2-oxobutyrate and triethyl phosphonoacetate. The key steps of the sequence included a Horner-Wadsworth-Emmons condensation to obtain the precursor farinomalein A and coupling with suitable alcohols to install the chain. The synthesis of farinomalein D has been achieved starting from (R)-isopropylideneglycerol on the basis of which the S configuration was assigned to the natural compound. The antifungal activity of the synthesized compounds was evaluated against Cladosporium cladosporioides. (C) 2014 Elsevier Ltd. All rights reserved.
• Improved Synthesis of Farinomalein and Its Analogs
  作者：Sachin T. Aiwale、Paola Sardi、Sabrina Dallavalle

  DOI：10.1080/00397911.2011.640969

  日期：2013.5.15

  Abstract A practical and convenient synthesis of the fungicidal natural compound farinomalein is described starting from readily available ethyl 3-methyl-2-oxobutyrate and triethyl phosphonoacetate, employing a Horner–Wadsworth–Emmons condensation as the key step. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications® to view the free

  摘要描述了一种实用且方便的杀真菌天然化合物粉状马来酸的合成方法，该合成方法以现成的 3-甲基-2-氧代丁酸乙酯和膦酰基乙酸三乙酯为起始原料，关键步骤为霍纳-沃兹沃思-埃蒙斯缩合反应。补充材料可用于本文。转至出版商的 Synthetic Communications® 在线版以查看免费的补充文件。图形概要