1,1-dimethoxynon-2-en-4-one | 1254182-85-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,1-dimethoxynon-2-en-4-one
• CAS: 1254182-85-8
• 化学式: C₁₁H₂₀O₃
• 分子量: 200.278
• InChiKey: RDRGCXRHCIJXRS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.31
• 重原子数：
  14.0
• 可旋转键数：
  8.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  35.53
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  1,1-dimethoxynon-2-en-4-one 在 盐酸 、 水 作用下， 生成 4-oxo-non-2-enal
  参考文献：
  名称：

  Lipid Peroxidation Generates Body Odor Component trans-2-Nonenal Covalently Bound to Protein in Vivo

  摘要：

  trans-2-Nonenal is an unsaturated aldehyde with an unpleasant greasy and grassy odor endogenously generated during the peroxidation of polyunsaturated fatty acids. 2-Nonenal covalently modified human serum albumin through a reaction in which the aldehyde preferentially reacted with the lysine residues. Modified proteins were immunogenic, and a specific monoclonal antibody (mAb) 27Q4 that cross-reacted with the protein covalently modified with 2-nonenal was raised from mouse. To verify the presence of the protein-bound 2-nonenal in vivo, the mAb 27Q4 against the 2-nonenal-modified keyhole limpet hemocyanin was raised. It was found that a novel 2-nonenal-lysine adduct, cis- and trans-N-epsilon-3-[(hept-1-enyl)-4-hexyl-pyridinium]lysine (HHP-lysine), constitutes an epitope of the antibody. The immunoreactive materials with mAb 27Q4 were detected in the kidney of rats exposed to ferric nitrilotriacetate, an iron chelate that induces free radical-mediated oxidative tissue damage. Using high performance liquid chromatography with on-line electrospray ionization tandem mass spectrometry, we also established a highly sensitive method for detection of the cis- and trans-HHP-lysine and confirmed that the 2-nonenal-lysine adducts were indeed formed during the lipid peroxidation-mediated modification of protein in vitro and in vivo. Furthermore, we examined the involvement of the scavenger receptor lectin-like oxidized low density lipoprotein receptor-1 in the recognition of 2-nonenal-modified proteins and established that the receptor recognized the HHP-lysine adducts as a ligand.

  DOI：

  10.1074/jbc.m109.068023
• 作为产物：
  描述：

  4-hydroxy-2-nonenal dimethyl acetal 在 pyridinium chlorochromate 作用下， 生成 1,1-dimethoxynon-2-en-4-one
  参考文献：
  名称：

  Lipid Peroxidation Generates Body Odor Component trans-2-Nonenal Covalently Bound to Protein in Vivo

  摘要：

  trans-2-Nonenal is an unsaturated aldehyde with an unpleasant greasy and grassy odor endogenously generated during the peroxidation of polyunsaturated fatty acids. 2-Nonenal covalently modified human serum albumin through a reaction in which the aldehyde preferentially reacted with the lysine residues. Modified proteins were immunogenic, and a specific monoclonal antibody (mAb) 27Q4 that cross-reacted with the protein covalently modified with 2-nonenal was raised from mouse. To verify the presence of the protein-bound 2-nonenal in vivo, the mAb 27Q4 against the 2-nonenal-modified keyhole limpet hemocyanin was raised. It was found that a novel 2-nonenal-lysine adduct, cis- and trans-N-epsilon-3-[(hept-1-enyl)-4-hexyl-pyridinium]lysine (HHP-lysine), constitutes an epitope of the antibody. The immunoreactive materials with mAb 27Q4 were detected in the kidney of rats exposed to ferric nitrilotriacetate, an iron chelate that induces free radical-mediated oxidative tissue damage. Using high performance liquid chromatography with on-line electrospray ionization tandem mass spectrometry, we also established a highly sensitive method for detection of the cis- and trans-HHP-lysine and confirmed that the 2-nonenal-lysine adducts were indeed formed during the lipid peroxidation-mediated modification of protein in vitro and in vivo. Furthermore, we examined the involvement of the scavenger receptor lectin-like oxidized low density lipoprotein receptor-1 in the recognition of 2-nonenal-modified proteins and established that the receptor recognized the HHP-lysine adducts as a ligand.

  DOI：

  10.1074/jbc.m109.068023

文献信息

• Enantioselective Friedel-Crafts Alkylation of Furans and Indoles with Simple α,β-Unsaturated Ketones Catalyzed by Oxazaborolidinone
  作者：Toshiro Harada、Shinya Adachi、Fumi Tanaka、Kazuya Watanabe、Atsushi Watada

  DOI：10.1055/s-0029-1218821

  日期：2010.8

  allo-Threonine-derived oxazaborolidinone (OXB) catalyzes the Friedel-Crafts alkylation of furans and indoles with simple acyclic α,β-unsaturated ketones to give the products in high yields and with high enantioselectivities. With 5-10 mol% of the OXB catalyst, enantioselectivities of up to 94% ee could be achieved for a variety of substrates. The use of N,N-dimethylaniline (2.5-10 mol%) as an additive

  同种异体-苏氨衍生oxazaborolidinone（OXB）催化呋喃和吲哚用简单的无环α，β不饱和酮的弗瑞德-克莱福特烷基化，得到产物以高产率和高对映选择性。使用5-10 mol％的OXB催化剂，对于多种底物，可以实现高达94％ee的对映选择性。已发现使用N，N-二甲基苯胺（2.5-10mol％）作为添加剂对于对映选择性是必不可少的。根据质子催化的外消旋途径的阻滞讨论了添加剂的作用，这阻碍了Friedel-Crafts反应的对映选择性。 不对称催化-烯酮-Friedel-Crafts反应-呋喃-吲哚