(2E)-4,5-dioxo-2-hexadecenoic acid ethyl ester | 135863-70-6

• 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: (2E)-4,5-dioxo-2-hexadecenoic acid ethyl ester
• 英文别名: ethyl (E)-4,5-dioxo-2-hexadecenoate；podoscyphic acid ethyl ester；ethyl (E)-4,5-dioxohexadec-2-enoate
• CAS: 135863-70-6
• 化学式: C₁₈H₃₀O₄
• 分子量: 310.434
• InChiKey: LQOVGJZNKREJKN-CCEZHUSRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  22
• 可旋转键数：
  15
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  60.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2E)-4,5-dioxo-2-hexadecenoic acid ethyl ester 在 Candida antarctica lipase B 作用下， 以 水 为溶剂， 反应 2.0h， 以70%的产率得到(E)-4,5-二氧代十六碳-2-烯酸
  参考文献：
  名称：

  Synthesis of podoscyphic acid

  摘要：

  Podoscyphic acid 1, a fungal metabolite inhibiting RNA-directed DNA polymerises, was synthesised in four steps starting from dodecanal. The concluding ester hydrolysis of 4 was not feasible with chemical reagents, only enzymatic hydrolysis was mild enough to release the highly reactive natural product in good yields. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)02264-x
• 作为产物：
  描述：

  十二醛 在 奎宁环 、 甲基磺酰胺 2,2,6,6-tetramethyl-piperidine-N-oxyl 、 四氧化锇 、 potassium carbonate 、 potassium hexacyanoferrate(III) 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 叔丁醇 为溶剂， 反应 96.0h， 生成 (2E)-4,5-dioxo-2-hexadecenoic acid ethyl ester
  参考文献：
  名称：

  Synthesis of podoscyphic acid

  摘要：

  Podoscyphic acid 1, a fungal metabolite inhibiting RNA-directed DNA polymerises, was synthesised in four steps starting from dodecanal. The concluding ester hydrolysis of 4 was not feasible with chemical reagents, only enzymatic hydrolysis was mild enough to release the highly reactive natural product in good yields. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)02264-x

文献信息

• Imidazo[1,2-a]pyridine derivatives as inhibitors of TNF-α expression in T cells
  作者：Jan Rether、Gerhard Erkel、Timm Anke、Johan Bajtner、Olov Sterner

  DOI：10.1016/j.bmc.2007.10.074

  日期：2008.2.1

  Novel hexahydroimidazo[1,2-a]pyridines prepared by the addition of ethyl (1-benzylimidazolidin-2-ylidene)acetate (2) to the fungal metabolite podoscyphic acid (1a) and esters of la have been evaluated for their ability to inhibit the inducible TNF-alpha promoter activity in T cells. The methyl ester 3b is the most potent, inhibiting the TNF-alpha driven reporter gene expression in Jurkat T cells with an IC50-value of 2.0 mu g/ml (3.6 mu M). In addition, compound 3b inhibited the inducible TNF-alpha production in the myelomonocytic U937 cells with an IC50-value of 4.6 mu M. (c) 2007 Elsevier Ltd. All rights reserved.
• Tandem Oxidation Sequence to Prepare Ethyl (<i>E</i>)‐4,5‐Dioxo‐2‐hexadecenoate: A Formal Synthesis of Podoscyphic Acid
  作者：Cecilia Devi Wilfred、Richard J. K. Taylor

  DOI：10.1080/00397910500297206

  日期：2005.11

  A tandem oxidation reaction has been utilized to prepare ethyl (E)-4,5-dioxo-2-hexadecenoate, the immediate precusor to the antiviral fungal metabolite podoscyphic acid.
• Synthesis of podoscyphic acid
  作者：Johan Eriksson、Martin Johansson、Olov Sterner

  DOI：10.1016/s0040-4039(01)02264-x

  日期：2002.1

  Podoscyphic acid 1, a fungal metabolite inhibiting RNA-directed DNA polymerises, was synthesised in four steps starting from dodecanal. The concluding ester hydrolysis of 4 was not feasible with chemical reagents, only enzymatic hydrolysis was mild enough to release the highly reactive natural product in good yields. (C) 2002 Elsevier Science Ltd. All rights reserved.