farinomalein E | 1414774-74-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: farinomalein E
• 英文别名: 1H-Pyrrole-1-propanoic acid, 2,5-dihydro-3-(1-methylethyl)-2,5-dioxo-, (3E)-4-carboxy-3-methyl-3-buten-1-yl ester；(E)-5-[3-(2,5-dioxo-3-propan-2-ylpyrrol-1-yl)propanoyloxy]-3-methylpent-2-enoic acid
• CAS: 1414774-74-5
• 化学式: C₁₆H₂₁NO₆
• 分子量: 323.346
• InChiKey: XBJGLGIHWMWNGL-DHZHZOJOSA-N

物化性质

• 沸点：
  512.4±45.0 °C(Predicted)
• 密度：
  1.239±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  23
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  101
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  3-甲基-2-氧代丁酰乙酯 在 4-二甲氨基吡啶 、 sodium hydride 、 lithium hydroxide 作用下， 以 四氢呋喃 、 二氯甲烷 、 溶剂黄146 为溶剂， 反应 11.17h， 生成 farinomalein E
  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

文献信息

• Stereoselective Syntheses of <i>trans</i>-Anhydromevalonic Acid and <i>trans</i>-Anhydromevalonyl Group-Containing Natural Products
  作者：Atsushi Nakayama、Yoko Yasuno、Yuki Yamamoto、Kai Saito、Kohei Kitsuwa、Hironori Okamura、Tetsuro Shinada

  DOI：10.1021/acs.jnatprod.1c01176

  日期：2022.4.22

  Collective total syntheses of trans-anhydromevalonic acid (tAHMA) and trans-anhydromevalonyl (tAHM) group-containing natural products (pestalotiopin A, pestalotiopamide C, pestalotiopamide D, farinomalein E, eleutherazine B, and trichocyclodipeptide A) were achieved using tAHMA esters as key intermediates. To this end, tAHMA tert-butyl ester was newly prepared by Z-vinyltosylation of tert-butyl 3-

  使用tAHMA酯作为关键，实现了反式-脱水甲羟戊酸 (tAHMA) 和反式-脱水甲羟戊酸 (tAHM) 基团的天然产物（pestalotiopin A、pestalotiopamide C、pestalotiopamide D、farinomalein E、eleutherazine B 和 trichocyclodipeptide A）的集体全合成中间体。为此，通过 3-氧代-5-((三异丙基甲硅烷基)氧基)戊酸叔丁酯的 Z-乙烯基甲苯基化，然后与 Me 2 Zn进行 Negishi 交叉偶联反应，新制备了tAHMA叔丁酯。tAHMA 酯通过酯化或酰胺化转化为目标天然产物。合成和天然产物的光谱数据的比较证实了天然产物中 tAHM 部分的E构型。
• 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.