12-amino-12-oxododecanoic acid | 21842-33-1

• 物质功能分类: 有机原料 - 羧酸类化合物及衍生物 - 无环羧酸
• 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: 12-amino-12-oxododecanoic acid
• 英文别名: 1,12-dodecandioic monoamide；11-carbamoylundecanoic acid；11-carbamoyl-undecanoic acid；11-Carbamoyl-undecansaeure；11-Carbonylundecansaeure；Dodecandisaeuremonoamid
• CAS: 21842-33-1
• 化学式: C₁₂H₂₃NO₃
• 分子量: 229.32
• InChiKey: RAFOGKOTRLOFKP-UHFFFAOYSA-N

物化性质

• 熔点：
  143 °C(Solv: water (7732-18-5); ethanol (64-17-5))
• 沸点：
  442.5±18.0 °C(Predicted)
• 密度：
  1.032±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  16
• 可旋转键数：
  11
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  80.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  12-amino-12-oxododecanoic acid 在 sodium hydroxide 、 溴 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 17.25h， 生成 11-氨基十一酸
  参考文献：
  名称：

  藜芦酸合成12-氨基十二烷酸和11-氨基十一烷酸

  摘要：

  Abstract12‐Aminododecanoic acid and 11‐aminoundecanoic acid, monomer precursors for nylon‐12 and nylon‐11, respectively, have been synthesized from vernolic (cis‐12,13‐epoxy‐cis‐9‐octadecenoic) acid via a reaction sequence that includes the formation of 12‐oxododecanoic acid oxime. Saponification of vernonia oil, followed by a low‐temperature recrystallization at −20°C, gave 51% vernolic acid (97% purity, m.p. 23–25°C). Hydrogenation afforded cis‐12,13‐epoxystearic acid (m.p. 52–54°C, lit. m.p. 52–54°C), which upon oxidation with periodic acid in tertiary butyl alcohol gave 12‐oxododecanoic acid with an isolated yield of 71.0%. Reaction of the oxoacid with hydroxylamine hydrochloride gave 12‐oxododecanoic acid oxime, which was catalytically reduced to give 12‐aminododecanoic acid with a yield greater than 85% and a melting point of 184–186°C (lit. m.p. 185–187°C). 11‐Aminoundecanoic acid was prepared from the 12‐oxododecanoic acid oxime via a three‐step reaction sequence that involved a Beckmann rearrangement, Hofmann degradation, and hydrolysis. Thus, the aldoxime acid was hydrolyzed in the presence of nickel acetate tetrahydrate to give 11‐carbamoylundecanoic acid (48% yield, m.p. 129–131°C, lit. m.p. 129–130°C). The amide was then treated with a solution of sodium methoxide and bromine at 70–80°C to give 11‐(methoxycarbonylamino)undecanoic acid at 75% yield (m.p. 84–86°C; elemental analysis, calculated for C13H25NO4: C, 60.19; H, 9.73; N, 5.40; O, 24.68%; found C, 60.02; H, 9.81; N, 5.26; O, 24.91%), which upon alkaline hydrolysis and subsequent neutralization gave 11‐aminoundecanoic acid at 34% yield (m.p. 189–192°C, lit. m.p. 190°C). Mass spectrometric and 13C nuclear magnetic resonance data of the previously unreported 11‐(methoxycarbonylamino)undecanoic acid is provided.

  DOI：

  10.1007/s11746-997-0176-z
• 作为产物：
  描述：

  cyclododecane-1,2-dione monoxime 在 硫酸 作用下， 生成 12-amino-12-oxododecanoic acid
  参考文献：
  名称：

  Syntheses and the Beckmann Fission of Cyclic α-Hydroxyimino Ketones

  摘要：

  已建立了一种方便的方法，通过环状烷酮与氯化亚氮反应制备α-羟基亚肟环状酮。这些α-羟基亚肟酮经过贝克曼 rearrangement 反应，良好产率地得到ω-氰基羧酸或其衍生物。

  DOI：

  10.1246/bcsj.46.3474

文献信息

• [EN] NOVEL THIOPHENE AMIDINES, COMPOSITIONS THEREOF, AND METHODS OF TREATING COMPLEMENT-MEDIATED DISEASES AND CONDITIONS<br/>[FR] NOUVELLES AMIDINES DE THIOPHENE, COMPOSITIONS DE CES AMIDINES ET PROCEDE POUR TRAITER DES MALADIES ET DES ETATS MEDIES PAR LE COMPLEMENT
  申请人：DIMENSIONAL PHARM INC

  公开号：WO2003099805A1

  公开（公告）日：2003-12-04

  Disclosed is a method for treating the symptoms of an acute or chronic disorder mediated by the classical pathway of the complement cascade, comprising administering to a mammal in need of such treatment a therapeutically effective amount of a compound of Formula (I) or a solvate, hydrate or pharmaceutically acceptable salt thereof; wherein R1, R2, R3, R4 and R7 are defined in the specification, Z is SO or SO2, and Ar is an aromatic or heteroaromatic group as defined herein.

  揭示了一种治疗急性或慢性疾病症状的方法，该方法通过补体级联的经典途径介导，包括向需要此类治疗的哺乳动物施用化合物I的治疗有效量或其溶剂化合物、水合物或药用可接受盐；其中规范中定义了R1、R2、R3、R4和R7，Z为SO或SO2，Ar为本规范中定义的芳香族或杂环芳基。
• Novel thiophene amidines, compositions thereof, and methods of treating complement-mediated diseases and conditions
  申请人：3-Dimensional Pharmaceuticals, Inc.

  公开号：US20040009995A1

  公开（公告）日：2004-01-15

  Disclosed is a method for treating the symptoms of an acute or chronic disorder mediated by the classical pathway of the complement cascade, comprising administering to a mammal in need of such treatment a therapeutically effective amount of a compound of Formula I 1 or a solvate, hydrate or pharmaceutically acceptable salt thereof; wherein R 1 , R 2 , R 3 , R 4 and R 7 are defined in the specification, Z is SO or SO 2 , and Ar is an aromatic or heteroaromatic group as defined herein.

  揭示了一种治疗急性或慢性疾病症状的方法，该方法通过补体级联的经典途径介导，包括向需要此类治疗的哺乳动物施用公式I的化合物的治疗有效量或其溶剂化合物、水合物或药用可接受盐；其中在规范中定义了R1、R2、R3、R4和R7，Z为SO或SO2，Ar为本文中定义的芳香族或杂环芳基。
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  作者：Cosimo Annese、Lucia D'Accolti、Caterina Fusco、Giulia Licini、Cristiano Zonta

  DOI：10.1002/chem.201604507

  日期：2017.1.5

  in the oxidation of lactams moving from dimethyl dioxirane (DDO) to methyl(trifluoromethyl)dioxirane (TFDO). A physical organic chemistry study, which combines the oxidation with two other dioxiranes methyl(fluoromethyl)dioxirane, MFDO, and methyl(difluoromethyl)dioxirane, DFDO, with computational studies, points to a diverse ability of the dioxiranes to either stabilize the homo or the heterolytic

  二恶英是强大的氧化剂，可通过两种不同的机制起作用：1）均溶（H提取和氧回弹）和2）杂溶（亲电子氧化）。迄今为止，已经报道了底物的性质决定了反应模式，而与所使用的二环氧乙烷无关。在此，我们报道了前所未有的情况，其中二环氧乙烷的性质决定了氧化化学选择性。特别是，在内酰胺从二甲基二环氧乙烷（DDO）转移到甲基（三氟甲基）二环氧乙烷（TFDO）的内酰胺氧化中观察到了从CH到NH的转换。一项物理有机化学研究，将氧化与其他两种二氧杂环戊烷甲基（氟甲基）二环氧乙烷，MFDO和甲基（二氟甲基）二环氧乙烷相结合，通过计算研究，DFDO指出二恶英类化合物具有稳定同源或杂合途径的多种能力。
• Amyloid-β Peptide Targeting Peptidomimetics for Prevention of Neurotoxicity
  作者：Dmytro Honcharenko、Alok Juneja、Firoz Roshan、Jyotirmoy Maity、Lorena Galán-Acosta、Henrik Biverstål、Erik Hjorth、Jan Johansson、André Fisahn、Lennart Nilsson、Roger Strömberg

  DOI：10.1021/acschemneuro.8b00485

  日期：2019.3.20

  between ligand and Aβ, compared to first-generation ligands. The synthesis of selected novel Aβ-targeting ligands was performed in solution via an active ester coupling approach or on solid-phase using an Fmoc chemistry protocol. This included incorporation of aliphatic hydrocarbon moieties, a branched triamino acid with an aliphatic hydrocarbon tail, and an amino acid with a 4′-N,N-dimethylamino-1,8-naphthalimido

  提出了设计用于与淀粉样β肽（Aβ）的α-螺旋/β链不一致区相互作用并抵消其低聚作用的新一代配体。这些配体被设计为通过结合几种第一代配体的性质与aβ中心螺旋（残基13–26）相互作用并使其稳定在a螺旋构象中，并具有增强的相互作用。新的肽样配体旨在跨Aβ中心部分扩展疏水和极性接触，即“钳住”靶标。进行了一系列第二代配体存在下Aβ中心螺旋稳定性的分子动力学（MD）模拟，并揭示了Aβα-螺旋构象的进一步稳定，且配体与Aβ之间存在更多的极性和非极性接触。与第一代配体相比，Aβ。选择的新颖的靶向Aβ的新配体的合成是通过活性酯偶联方法在溶液中进行的，或者使用Fmoc化学方案在固相上进行的。这包括掺入脂族烃部分，带有脂族烃尾部的支链三氨基酸和具有4'-侧链中的N，N-二甲基氨基-1，8-萘二甲酰亚胺基。通过海马切片制剂中的伽马振荡实验评估了配体降低Aβ1–42神经毒性的能力。发现“钳位”的第二代配体是有效
• Reactions of organic peroxides. Part X. Amino-peroxides from cyclohexanone
  作者：E. G. E. Hawkins

  DOI：10.1039/j39690002663

  日期：——

  Reaction of cyclohexanone with hydrogen peroxide and ammonia gives either 1,1′-peroxydicyclohexylamine or 1-hydroperoxycyclohexylamine, depending on the ketone to hydrogen peroxide ratio. The reactions of these peroxy-amines studied include (i) base-catalysed conversion of 1,1′-peroxydicyclohexylamine into caprolactam and cyclohexanone, (ii) vapour-phase pyrolysis of 1,1′-peroxydicyclohexylamine to

  环己酮与过氧化氢和氨的反应生成1,1'-过氧二环己胺或1-氢过氧环己胺，具体取决于酮与过氧化氢的比例。研究的这些过氧胺的反应包括（i）1，1'-过氧二环己胺碱催化转化为己内酰胺和环己酮，（ii）1，1'-过氧二环己胺的气相热解为癸烷-1,10-二碳酰亚胺，11-氰基十一烷酸，己内酰胺和环己酮，以及（iii）用钨酸盐催化剂将1-氢过氧环己胺转化为环己酮肟。