methyl 12-nitrododecanoate | 13154-47-7

• 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: methyl 12-nitrododecanoate
• CAS: 13154-47-7
• 化学式: C₁₃H₂₅NO₄
• 分子量: 259.346
• InChiKey: SJVAZOSTYXOYOA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  18
• 可旋转键数：
  12
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  72.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 12-nitrododecanoate 在 氢氧化钾 、 sodium tetrahydroborate 、 potassium permanganate 、 magnesium sulfate 作用下， 以 甲醇 、 水 为溶剂， 反应 0.25h， 生成 methyl 12-hydroxydodecanoate
  参考文献：
  名称：

  Amberlyst A 21 as New and Efficient Surface Catalyst for the Cleavage of 2-Nitrocycloalkanones

  摘要：

  甲醇/Amberlyst A 21 条件下，2-硝基环烷酮的开环裂解反应高产率地生成了甲基 ƴ-硝基烷酸酯，其中 O2NCH2(CH2)nCO2Me（n = 3-6, 8-10, 13）。随后的 Nef 反应得到相应的 ƴ-氧代化合物，这些化合物被分离出来，仅限于甲基 7-氧代庚酸酯和甲基 8-氧代辛酸酯，或者直接用硼氢化钠还原得到 ƴ-羟基烷酸酯。此外，还报道了一种 exaltolide（15-十五烷酸内酯）的新型正式合成方法。

  DOI：

  10.1055/s-1992-26106
• 作为产物：
  描述：

  在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 2.5h， 以1.27 g的产率得到methyl 12-nitrododecanoate
  参考文献：
  名称：

  Activation of Peroxisome Proliferator-Activated Receptor γ (PPARγ) by Nitroalkene Fatty Acids: Importance of Nitration Position and Degree of Unsaturation

  摘要：

  Nitroalkene fatty acids are potent endogenous ligand activators of PPAR gamma-dependent transcription. Previous studies with the naturally occurring regioisomers of nitrolinoleic acid revealed that the isomers are not equivalent with respect to PPAR gamma activation. To gain further insight into the structure-activity relationships between nitroalkenes and PPAR gamma, we examined additional naturally occurring nitroalkenes derived from oleic acid, 9-nitrooleic acid (E-9-NO2-18:1 [1]) and 10-nitrooleic acid (E-10-NO2-18:1 [2]), and several synthetic nitrated enoic fatty acids of variable carbon chain length, double bonds, and nitration site. At submicromolar concentrations, E-12-NO2 derivatives were considerably more potent than isomers nitrated at carbons 5, 6, 9, 10, and 13, and chain length (16 versus 18) or number of double bonds (1 versus 2) was of little consequence for PPAR gamma activation. Interestingly, at higher concentrations (> 2 mu M) the nitrated enoic fatty acids (E-9-NO2-18:1 [1], E-9-NO2-16:1 [3], E-10-NO2-18:1 [2], and E-12-NO2-18:1 [7]) deviated significantly from the saturable pattern of PPAR gamma activation observed for nitrated 1,4-dienoic fatty acids (E-9-NO2-18:2, E-10-NO2-18:2, E-12-NO2-18:2, and E-13-NO2-18:2).

  DOI：

  10.1021/jm900326c

文献信息

• Synthesis of 3-Alkyl-2,5-dimethylfuran Derivatives by Indirect Alkylation of 2,5-Dimethylfuran with Aliphatic Nitrocompounds
  作者：Roberto Ballini、Giovanna Bosica、Dennis Fiorini、Guido Giarlo

  DOI：10.1055/s-2001-17714

  日期：——

  The preparation of 3-alkyl-2,5-dimethylfuranes via indirect alkylation of 2,5-dimethylfuran is reported. Thus, primary nitroalkanes react with cis-3-hexen-2,5-dione giving a tandem Michael addition/elimination of nitrous acid, followed by chemoselective hydrogenation of the C=C double bond of the obtained enones. The Paal-Knorr reaction, performed with p-toluenesulfonic acid in diethyl ether, completes the formation of the title compounds. In this context the nitroalkane can be considered as an alkyl cation synthon.

  报告了通过间接烷基化2,5-二甲基呋喃制备3-烷基-2,5-二甲基呋喃的方法。因此，初级硝基烷与顺式-3-己烯-2,5-二酮反应，产生硝酸的串联迈克尔加成/消除反应，随后对得到的烯酮的C=C双键进行选择性氢化。使用对甲基苯磺酸在二乙醚中进行的Paal-Knorr反应完成了目标化合物的形成。在这个背景下，硝基烷可以被视作烷基阳离子的合成单位。
• A New Synthesis of <b><i>exo</i></b>-Methylene Butyrolactones from Nitroalkanes
  作者：Roberto Ballini、Giovanna Bosica、Damiana Livi

  DOI：10.1055/s-2001-16098

  日期：——

  A versatile route to exo-methylene butyrolactones was developed by employing a three step reaction sequence consisting of Michael addition of primary nitroalkanes 1 to ethyl (2-bromomethyl)acrylate (2), then Nef conversion of the nitro derivatives 3, and subsequent lactonization of the obtained keto esters 4. The method is chemoselective for important functionalities such as ester, C=C double bond and hydroxyl.

  开发了一种多功能的路线用于exo-亚甲基丁内酯，通过采用三步反应序列实现，首先是将一烷基硝基烷1与乙基(2-溴甲基)丙烯酸酯2进行迈克尔加成，然后对得到的硝基衍生物3进行内夫转化，最后对所获得的酮酯4进行内酯化。该方法对酯、C=C双键和羟基等重要官能团具有化学选择性。
• US3933873A
  申请人：——

  公开号：US3933873A

  公开（公告）日：1976-01-20
• Amberlyst A 21 as New and Efficient Surface Catalyst for the Cleavage of 2-Nitrocycloalkanones
  作者：Roberto Ballini、Marino Petrini、Valeria Polzonetti

  DOI：10.1055/s-1992-26106

  日期：——

  Ring cleavage of 2-Nitrocycloalkanones with methanol/Amberlyst A 21 gave methyl ω-nitroalkanoates, O2NCH2(CH2)nCO2Me where n = 3-6, 8-10, 13, in high yield. Subsequent Nef reaction gave the corresponding ω-oxo compounds which were isolated, in the case of methyl 7-oxoheptanoate and methyl 8-oxooctanoate only, or reduced directly with sodium borohydride to give ω-hydroxyalkanoates. A new formal synthesis of exaltolide (15-pentadecanolide) is also reported.

  甲醇/Amberlyst A 21 条件下，2-硝基环烷酮的开环裂解反应高产率地生成了甲基 ƴ-硝基烷酸酯，其中 O2NCH2(CH2)nCO2Me（n = 3-6, 8-10, 13）。随后的 Nef 反应得到相应的 ƴ-氧代化合物，这些化合物被分离出来，仅限于甲基 7-氧代庚酸酯和甲基 8-氧代辛酸酯，或者直接用硼氢化钠还原得到 ƴ-羟基烷酸酯。此外，还报道了一种 exaltolide（15-十五烷酸内酯）的新型正式合成方法。
• Activation of Peroxisome Proliferator-Activated Receptor γ (PPARγ) by Nitroalkene Fatty Acids: Importance of Nitration Position and Degree of Unsaturation
  作者：Michael J. Gorczynski、Pamela K. Smitherman、Taro E. Akiyama、Harold B. Wood、Joel P. Berger、S. Bruce King、Charles S. Morrow

  DOI：10.1021/jm900326c

  日期：2009.8.13

  Nitroalkene fatty acids are potent endogenous ligand activators of PPAR gamma-dependent transcription. Previous studies with the naturally occurring regioisomers of nitrolinoleic acid revealed that the isomers are not equivalent with respect to PPAR gamma activation. To gain further insight into the structure-activity relationships between nitroalkenes and PPAR gamma, we examined additional naturally occurring nitroalkenes derived from oleic acid, 9-nitrooleic acid (E-9-NO2-18:1 [1]) and 10-nitrooleic acid (E-10-NO2-18:1 [2]), and several synthetic nitrated enoic fatty acids of variable carbon chain length, double bonds, and nitration site. At submicromolar concentrations, E-12-NO2 derivatives were considerably more potent than isomers nitrated at carbons 5, 6, 9, 10, and 13, and chain length (16 versus 18) or number of double bonds (1 versus 2) was of little consequence for PPAR gamma activation. Interestingly, at higher concentrations (> 2 mu M) the nitrated enoic fatty acids (E-9-NO2-18:1 [1], E-9-NO2-16:1 [3], E-10-NO2-18:1 [2], and E-12-NO2-18:1 [7]) deviated significantly from the saturable pattern of PPAR gamma activation observed for nitrated 1,4-dienoic fatty acids (E-9-NO2-18:2, E-10-NO2-18:2, E-12-NO2-18:2, and E-13-NO2-18:2).