(E)-3-(5-oxotetrahydrofuran-2-yl)acrylaldehyde

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (E)-3-(5-oxotetrahydrofuran-2-yl)acrylaldehyde
• 英文别名: 5-(3-Oxo-1-propenyl)oxolane-2-one；(E)-3-(5-oxooxolan-2-yl)prop-2-enal
• 化学式: C₇H₈O₃
• 分子量: 140.139
• InChiKey: MGDPEFRLGBFRFH-OWOJBTEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-3-(5-oxotetrahydrofuran-2-yl)acrylaldehyde 在 sodium chlorite 、 sodium dihydrogenphosphate 、 2-甲基-2-丁烯 作用下， 以 四氢呋喃 、 水 、 叔丁醇 为溶剂， 反应 2.0h， 以83%的产率得到(E)-3-(5-oxotetrahydrofuran-2-yl)acrylic acid
  参考文献：
  名称：

  视网膜色素上皮细胞代谢4-羟基-7-氧代-5-庚烯酸（HOHA）内酯

  摘要：

  4-羟基-7-氧代-5-庚酸（HOHA）-内酯是一种释放出生物活性的氧化截短产物（t 1/2在二十二碳六烯酸酯脂质中进行非酶促酯交换/脱酰基反应，在37°C下30分钟）。我们现在报道，HOHA-内酯很容易扩散到视网膜色素上皮（RPE）细胞中进行代谢。LC-MS检测到，在细胞外培养基和细胞裂解物中，HOHA-内酯的还原型谷胱甘肽（GSH）迈克尔加合物是最突出的代谢产物。暴露于HOHA-内酯后数秒内，该分子出现在ARPE-19细胞内部。细胞内水平在30分钟时达到最大浓度，然后在细胞外培养基中水平随之升高而降低，因此揭示了还原的GSH-HOHA-内酯加合物从细胞质单向输出到细胞外培养基中。这种代谢可能会调节HOHA-内酯参与人类疾病的发病机理。HOHA-内酯具有生物活性，例如低浓度（0.1–1μM）会诱导ARPE-19细胞分泌血管内皮生长因子（VEGF）。HOHA-内酯还是蛋白质和乙醇胺磷脂中伯

  DOI：

  10.1021/acs.chemrestox.6b00153
• 作为产物：
  描述：

  环庚三烯 在 氨 、 氧气 、 tetraphenylporphyrin 、 lithium 、 iron(II) sulfate 、 三苯基膦 、 pyridinium chlorochromate 作用下， 以 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 18.33h， 生成 (E)-3-(5-oxotetrahydrofuran-2-yl)acrylaldehyde
  参考文献：
  名称：

  Fe²⁺ Catalyzes Vitamin E-Induced Fragmentation of Hydroperoxy and Hydroxy Endoperoxides That Generates γ-Hydroxy Alkenals

  摘要：

  The formation of cytotoxic gamma-hydroxyalkenals has been generally viewed as the consequence of free radical-induced oxidation of polyunsaturated fatty acyls through the decomposition of lipid peroxides. Vitamin E (Vit E) would be expected to inhibit such autoxidation. In a model study, we now find that fragmentation of a hydroperoxy endoperoxide generated the lactone of a gamma-hydroxyalkenal. With 1 equiv of Fe2+, or with a catalytic amount (0.1 equiv) of Fe2+ and 1 equiv of Vit E, the yields are 43-50%. However, Vit E alone did not promote the fragmentation, and a catalytic amount of Fe2+ alone only afforded a low yield (about 5%). Vit E could contribute to, as opposed to preventing, the formation of gamma-hydroxyalkenals by converting redox-active metal ions into their reduced forms that promote the rapid fragmentation of hydroperoxy endoperoxides.

  DOI：

  10.1021/ja0689785

文献信息

• An efficient synthesis of γ-hydroxy-α,β-unsaturated aldehydic esters of 2-lysophosphatidylcholine
  作者：Jaewoo Choi、James M. Laird、Robert G. Salomon

  DOI：10.1016/j.bmc.2010.10.058

  日期：2011.1

  4-hydroxy-7-oxohept-5-enoic acid ester of 2-lyso-phosphatidylcholine (HOHA-PC), the 5-hydroxy-8-oxo-6-octenoic acid ester of 2-lyso-PC (HOOA-PC), and the 9-hydroxy-12-oxododec-10-enoic acid ester of 2-lyso-PC (HODA-PC), are generated by oxidative cleavage of polyunsaturated fatty acyl phospholipids. To facilitate investigations of their chemistry and biology, we now report efficient total synthesis of HOOA, HODA

  γ-羟基链烯醛磷脂的多种生物活性及其与疾病的关系是深入研究的主题。磷脂醛，例如 2-溶血磷脂酰胆碱的 4-羟基-7-氧代庚烷-5-烯酸酯 (HOHA-PC)、2-溶血-磷脂酰胆碱的 5-羟基-8-氧代-6-辛烯酸酯PC (HOOA-PC) 和 2-lyso-PC 的 9-羟基-12-oxododec-10-烯酸酯 (HODA-PC) 是通过多不饱和脂肪酰基磷脂的氧化裂解产生的。为了促进对其化学和生物学的研究，我们现在报告了 HOOA、HODA 和 HOHA 磷脂的有效全合成。因为目标 γ-羟基烯醛很容易通过醛基氧化成羧酸或环化成呋喃而分解，
• The iron-mediated intramolecular addition of carboxylates to conjugated dienes
  作者：Ming-Chang P. Yeh、Li-Wen Chuang、Ya-Sheng Hsieh、Ming-Shan Tsai

  DOI：10.1039/a901628g

  日期：——

  Treatment of carboxylic acid functionalized (η4-diene)Fe(CO)3 complexes with 3.0 equiv. of NOBF4 in the presence of Et3N generates γ- and δ-lactones containing an α,β-unsaturated aldehyde or oxime functionality after NO+ insertion.

  在 Et3N 存在下，用 3.0 等量的 NOBF4 处理羧酸官能化的（η4-二烯）Fe(CO)3 复合物，在 NO+ 插入后生成含有 α、β-不饱和醛或肟官能团的 γ- 和 δ-内酯。
• Fe²⁺ Catalyzes Vitamin E-Induced Fragmentation of Hydroperoxy and Hydroxy Endoperoxides That Generates γ-Hydroxy Alkenals
  作者：Xiaodong Gu、Wujuan Zhang、Robert G. Salomon

  DOI：10.1021/ja0689785

  日期：2007.5.1

  The formation of cytotoxic gamma-hydroxyalkenals has been generally viewed as the consequence of free radical-induced oxidation of polyunsaturated fatty acyls through the decomposition of lipid peroxides. Vitamin E (Vit E) would be expected to inhibit such autoxidation. In a model study, we now find that fragmentation of a hydroperoxy endoperoxide generated the lactone of a gamma-hydroxyalkenal. With 1 equiv of Fe2+, or with a catalytic amount (0.1 equiv) of Fe2+ and 1 equiv of Vit E, the yields are 43-50%. However, Vit E alone did not promote the fragmentation, and a catalytic amount of Fe2+ alone only afforded a low yield (about 5%). Vit E could contribute to, as opposed to preventing, the formation of gamma-hydroxyalkenals by converting redox-active metal ions into their reduced forms that promote the rapid fragmentation of hydroperoxy endoperoxides.
• Metabolism of 4-Hydroxy-7-oxo-5-heptenoic Acid (HOHA) Lactone by Retinal Pigmented Epithelial Cells
  作者：Hua Wang、Mikhail Linetsky、Junhong Guo、Annabelle O. Yu、Robert G. Salomon

  DOI：10.1021/acs.chemrestox.6b00153

  日期：2016.7.18

  GSH-HOHA-lactone adduct from the cytosol to extracellular medium. This metabolism is likely to modulate the involvement of HOHA-lactone in the pathogenesis of human diseases. HOHA-lactone is biologically active, e.g., low concentrations (0.1–1 μM) induce secretion of vascular endothelial growth factor (VEGF) from ARPE-19 cells. HOHA-lactone is also a precursor of 2-(ω-carboxyethyl)pyrrole (CEP) derivatives

  4-羟基-7-氧代-5-庚酸（HOHA）-内酯是一种释放出生物活性的氧化截短产物（t 1/2在二十二碳六烯酸酯脂质中进行非酶促酯交换/脱酰基反应，在37°C下30分钟）。我们现在报道，HOHA-内酯很容易扩散到视网膜色素上皮（RPE）细胞中进行代谢。LC-MS检测到，在细胞外培养基和细胞裂解物中，HOHA-内酯的还原型谷胱甘肽（GSH）迈克尔加合物是最突出的代谢产物。暴露于HOHA-内酯后数秒内，该分子出现在ARPE-19细胞内部。细胞内水平在30分钟时达到最大浓度，然后在细胞外培养基中水平随之升高而降低，因此揭示了还原的GSH-HOHA-内酯加合物从细胞质单向输出到细胞外培养基中。这种代谢可能会调节HOHA-内酯参与人类疾病的发病机理。HOHA-内酯具有生物活性，例如低浓度（0.1–1μM）会诱导ARPE-19细胞分泌血管内皮生长因子（VEGF）。HOHA-内酯还是蛋白质和乙醇胺磷脂中伯