D,L-aminocaprylic acid methyl ester hydrochloride

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: D,L-aminocaprylic acid methyl ester hydrochloride
• 英文别名: DL-2-aminooctanoic acid methyl ester hydrochloride；2-hexyl glycine methyl ester hydrochloride；2-amino-octanoic acid methyl ester; hydrochloride；2-Amino-octansaeure-methylester; Hydrochlorid；methyl 2-aminooctanoate hydrochloride；methyl 2-aminooctanoate;hydrochloride
• 化学式: C₉H₁₉NO₂*ClH
• 分子量: 209.716
• InChiKey: DILACJJQGKYVOY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.88
• 重原子数：
  13
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  52.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  D,L-aminocaprylic acid methyl ester hydrochloride 在 三乙胺 、 sodium hydroxide 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  Regiodivergent Enantioselective γ-Additions of Oxazolones to 2,3-Butadienoates Catalyzed by Phosphines: Synthesis of α,α-Disubstituted α-Amino Acids and N,O-Acetal Derivatives

  摘要：

  Phosphine-catalyzed regiodivergent enantioselective C-2- and C-4-selective gamma-additions of oxazolones to 2,3-butadienoates have been developed. The C-4-selective gamma-addition of oxazolones occurred in a highly enantioselective manner when 2-aryl-4-alkyloxazol-5-(4H)-ones were employed as pronudeophiles. With the employment of 2-alkyl-4-aryloxazol-5-(4H)-ones as the donor, C-2-selective gamma-addition of oxazolones took place in a highly enantioselective manner. The C-4-selective adducts provided rapid access to optically enriched alpha,alpha-disubstituted alpha-amino acid derivatives, and the C-2-selective products led to facile synthesis of chiral N,O-acetals and gamma-lactols. Theoretical studies via DFT calculations suggested that the origin of the observed regioselectivity was due to the distortion energy that resulted from the interaction between the nudeophilic oxazolide and the electrophilic phosphonium intermediate.

  DOI：

  10.1021/jacs.5b10524
• 作为产物：
  描述：

  在 盐酸 、 水 作用下， 生成 D,L-aminocaprylic acid methyl ester hydrochloride
  参考文献：
  名称：

  Synthesis and bioactivity of novel 3-(1-hydroxyethylidene)-5-substituted-pyrrolidine-2,4-dione derivatives

  摘要：

  Ten novel 5-substituted derivatives of 3-(1-hydroxyethylidene)pyrrolidine-2,4-dione were synthesized. The compounds were confirmed by IR, H-1 NMR, MS and elemental analysis. The bioassay indicated that these compounds showed noticeable herbicidal activities, and compounds 6f and 6j exhibited excellent inhibitory activities against the stalk of Echinochloa crusgalli, with EC50 values of 94.4 and 72.7 mg/L, respectively. (C) 2012 Chun Long Yang. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.

  DOI：

  10.1016/j.cclet.2012.07.002

文献信息

• Enantioenriched α-substituted glutamates/pyroglutamates via enantioselective cyclopropenimine-catalyzed Michael addition of amino ester imines
  作者：Zara M Seibel、Jeffrey S Bandar、Tristan H Lambert

  DOI：10.3762/bjoc.17.134

  日期：——

  A procedure for the enantioselective synthesis of α-substituted glutamates and pyroglutamates via a cyclopropenimine-catalyzed Michael addition of amino ester imines is described. Enantioselectivities of up to 94% have been achieved, and a variety of functional groups were found to be compatible. The impact of the catalyst structure and imine substitution is discussed. Compared to other methods, this protocol allows for a broader and more enantioselective access to pyroglutamate derivatives.

  通过环丙烯亚胺催化的氨基酯亚胺的迈克尔加成，描述了一种合成α-取代谷氨酸和吡咯谷氨酸的对映选择性程序。已经实现了高达94%的对映选择性，并发现多种官能团是兼容的。讨论了催化剂结构和亚胺取代的影响。与其他方法相比，这种方案允许更广泛和更对映选择性地获得吡咯谷氨酸衍生物。
• SYNTHESIS AND CHARACTERIZATION OF PIPERAZINE-2,6-DIONES
  作者：Teresa Mancilla、Lourdes Canillo、Luis S. Zamudio-Rivera、Hiram I. Beltrán、Norberto Farán

  DOI：10.1080/00304940209355746

  日期：2002.2

  Our current interest in piperazine-2,6-dione 3 derivatives of a-amino acids prompted us to develop a methodology to obtain them from a-amino acid methyl ester hydrochlorides 2 and 2bromoacetamide. This paper describes a short, high yield synthesis and characterization of six new piperazine-2,6-diones 3b-g, as well as the known piperazine-2,6-dione 3a via 3+3 annulation. This method provides access to

  哌嗪二酮也称为二酮哌嗪，是最小的环肽，也是几种具有治疗特性的天然产品中的常见基序。研究表明，双二酮哌嗪对 Lewis 肺癌、肉瘤 180、L12 10 白血病、P388 白血病、B 16 骨髓瘤、恶性淋巴瘤、C-26 结肠癌、C-38 人结肠癌和乳腺癌具有抗肿瘤活性。 2-8也被用于临床试验联合治疗？进一步的研究旨在确定这些药物影响细胞生长的机制。'O'~哌嗪-2,6-二酮在第 3 位和第 4 位取代已显示出降血脂活性，3-取代的类似物更具活性，并阐明对小鼠正常和诱导的高脂血症均有效。14 制备哌嗪-2,6-二酮的可用方法很少。它们是由多肽、1sl6 亚氨基二乙酸和甲酸铵，17 通过还原 2,6dibenzyloxypyrazineI8 和用盐酸水解 4-benzyl-2,6-bishydroxyiminopiperazine 制备的。Iy 我们目前对哌嗪-2,6-dione 3 的兴趣α
• Novel quaternary ammonium compounds
  申请人：Sasahara Takehiko

  公开号：US20050009805A1

  公开（公告）日：2005-01-13

  [Object] To provide a medicine useful for treatment and prevention of hyperlipidemia, further for the treatment and prevention of cholestasis-accompanying hepatopathy, particularly primary biliary cirrhosis and primary sclerosing cholangitis, and for the treatment and prevention of obesity and fatty liver. [Means] A benzothiazepine compound represented by the following formula (1), having a thioamide bond and a quaternary ammonium substituent.

  提供一种用于治疗和预防高脂血症，尤其是原发性胆汁性肝病，特别是原发性胆汁性肝硬化和原发性硬化性胆管炎，以及治疗和预防肥胖和脂肪肝的药物。代表如下式（1）的苯并噻二唑化合物，具有硫酰胺键和季铵基取代基。
• Novel benzothiazepine and bensothiepine compounds
  申请人：Sasahara Takehiko

  公开号：US20070190041A1

  公开（公告）日：2007-08-16

  A pharmaceutical useful as a therapeutic agent and a preventive agent for hyperlipemia, and a pharmaceutical useful as a therapeutic agent and a preventive agent for hepatic disorders associated with cholestasis, particularly, primary biliary cirrhosis and primary sclerosing cholangitis, and a pharmaceutical useful as a therapeutic agent and a preventive agent for obesity, fatty liver and steatohepatitis are provided. A benzothiazepine or benzothiepine compound represented by the following formula (1A) having a thioamide bond and a quaternary ammonium substitutent:

  提供了一种药物，可用作治疗和预防高脂血症的治疗剂和预防剂，以及一种药物，可用作治疗和预防与胆汁淤积有关的肝脏疾病，特别是原发性胆汁性肝硬化和原发性硬化性胆管炎的治疗剂和预防剂，以及一种药物，可用作治疗和预防肥胖症、脂肪肝和脂肪性肝炎的治疗剂和预防剂。化合物的苯并噻吩或苯并噻环代表如下式（1A），具有硫酰胺键和季铵取代基：
• Accessing Chiral Pyrrolodiketopiperazines under Organocatalytic Conditions
  作者：Eider Duñabeitia、Aitor Landa、Rosa López、Claudio Palomo

  DOI：10.1021/acs.orglett.2c03924

  日期：2023.1.13

  The production of chiral pyrrolodiketopiperazines under organocatalytic conditions demonstrates the capacity of bicyclic acylpyrrol lactims to perform as pronucleophiles in direct carbon–carbon bond forming reactions. The good performance of ureidoaminal-derived Brønsted bases in the Michael addition to nitroolefins affords these heterocyclic scaffolds with high skeleton diversity.

  在有机催化条件下生产手性吡咯二酮哌嗪证明了双环酰基吡咯内酰亚胺在直接碳-碳键形成反应中作为亲核试剂的能力。脲醛衍生的布朗斯台德碱在硝基烯烃的迈克尔加成中的良好性能为这些杂环支架提供了高骨架多样性。