(R)-farinomalein D

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 甘油脂
• 英文名称: (R)-farinomalein D
• 英文别名: [(2R)-2,3-dihydroxypropyl] 3-(2,5-dioxo-3-propan-2-ylpyrrol-1-yl)propanoate
• 化学式: C₁₃H₁₉NO₆
• 分子量: 285.297
• InChiKey: NLBWHYUPWSLMGR-SECBINFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  20
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  104
• 氢给体数：
  2
• 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 、 溶剂黄146 、 N,N'-二环己基碳二亚胺 、 lithium hydroxide 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 溶剂黄146 为溶剂， 反应 13.5h， 生成 (R)-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

文献信息

• 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.