N-benzyloxycarbonyl-L-alanine dimethylamide | 42718-51-4

• 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: N-benzyloxycarbonyl-L-alanine dimethylamide
• 英文别名: (S)-benzyl 1-(dimethylamino)-1-oxopropan-2-ylcarbamate；Cbz-L-alanineN,N-dimethyl amide；Z-Ala-NMe2；phenylmethyl [(1S)-2-(dimethylamino)-1-methyl-2-oxoethyl]carbamate；benzyl [(1S)-2-(dimethylamino)-1-methyl-2-oxoethyl]carbamate；((S)-1-dimethylcarbamoyl-ethyl)-carbamic acid benzyl ester；benzyl[(1S)-2-(dimethylamino)-1-methyl-2-oxo ethyl]carbamate；benzyl N-[(2S)-1-(dimethylamino)-1-oxopropan-2-yl]carbamate
• CAS: 42718-51-4
• 化学式: C₁₃H₁₈N₂O₃
• 分子量: 250.298
• InChiKey: FABGDABUBWEOOQ-JTQLQIEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  58.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-benzyloxycarbonyl-L-alanine dimethylamide 在 palladium on activated carbon 氢气 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、413.69 kPa 条件下， 反应 4.0h， 以97%的产率得到(2S)-2-氨基-N,N-二甲基-丙酰胺
  参考文献：
  名称：

  Modified amino acids

  摘要：

  本发明提供了一种一般式1的化合物， 其中X是CO-肼和NR1-草酸或酯基之间的连接，并提供了使用和合成方法。这些化合物代表氨基酸衍生物，其中氨基团通过草酸基转化为酸性基团，羧酸通过肼基转化为氨基功能团；以及包括该化合物的肽类似物和其合成方法。

  公开号：

  EP1826199A1
• 作为产物：
  描述：

  benzyl N-[2-(dimethylamino)-2-oxoethyl]-N-[(2R,6R)-6-methyloxan-2-yl]carbamate 在 sodium hexamethyldisilazane 、 三氟乙酸 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 24.5h， 生成 N-benzyloxycarbonyl-L-alanine dimethylamide
  参考文献：
  名称：

  6-Methyl δ-lactol derived chiral glycine equivalents for the asymmetric synthesis of protected α-amino amides

  摘要：

  Two new delta-lactol derived chiral glycine equivalents have been prepared in one-pot processes in good yields from the known 6-methyltetrahydropyran-2-ol. Alkylation proceeds in moderate to good yields and moderate to good selectivities under experimentally simple conditions. The lactol chiral auxiliary is readily removed under mild acidic conditions to give N-Cbz protected alpha-amino amides in good yields. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.01.026

文献信息

• Modified amino acids
  申请人：Technische Universität Wien

  公开号：EP1826199A1

  公开（公告）日：2007-08-29

  The present invention provides a compound of the general formula 1, wherein X is the connection between the CO-hydrazine and the NR1-oxalic acid or ester group, and uses and synthesis methods. These compounds represent amino acid derivatives, wherein the amine group is turned into an acidic group by the oxalic acid group and the carboxylic acid is turned into an amine functionality by the hydrazine group; as well as peptidomimetics comprising the compound and methods for their synthesis.

  本发明提供了一种一般式1的化合物， 其中X是CO-肼和NR1-草酸或酯基之间的连接，并提供了使用和合成方法。这些化合物代表氨基酸衍生物，其中氨基团通过草酸基转化为酸性基团，羧酸通过肼基转化为氨基功能团；以及包括该化合物的肽类似物和其合成方法。
• 1,3-Dihydro-2H-Indole-2-One Compound and Pyrrolidine-2-One Compound Fused With Aromatic Heterocycle
  申请人：Sekiguchi Yoshinori

  公开号：US20080318923A1

  公开（公告）日：2008-12-25

  It is intended to provide a drug which is efficacious against pathological conditions relating to arginine-vasopressin V1b receptor. More particularly speaking, it is intended to provide a drug which has a therapeutic or preventive effect on depression, anxiety, Alzheimer's disease, Parkinson's disease, Huntington's chorea, eating disorders, hypertension, digestive diseases, drug addiction, epilepsy, brain infarction, brain ischemia, brain edema, head injury, inflammation, immune diseases, alopecia and so on. As the results of intensive studies, a novel 1,3-dihydro-2H-indol-2-one compound and a pyrrolidin-2-one compound fused with a heteroaromatic ring, which are highly selective antagonists of arginine-vasopressin V1b receptor, have high metabolic stabilities and show favorable brain penetration and high plasma concentrations, are found, thereby achieving the above objective.

  旨在提供一种对与精氨酸加压素V1b受体相关的病理状况具有疗效的药物。更具体地说，旨在提供一种对抑郁症、焦虑症、阿尔茨海默病、帕金森病、亨廷顿舞蹈症、进食障碍、高血压、消化系统疾病、药物成瘾、癫痫、脑梗死、脑缺血、脑水肿、头部损伤、炎症、免疫疾病、脱发等具有治疗或预防作用的药物。经过深入研究，发现了一种新颖的1,3-二氢-2H-吲哚-2-酮化合物和与杂芳环融合的吡咯烷-2-酮化合物，它们是高度选择性的精氨酸加压素V1b受体拮抗剂，具有高代谢稳定性，表现出有利的血脑屏障穿透和高血浆浓度，从而实现了上述目标。
• Amidation Reaction of Carboxylic Acid with Formamide Derivative Using SO₃·pyridine
  作者：Shota Kawano、Kodai Saito、Tohru Yamada

  DOI：10.1246/cl.171216

  日期：2018.4.5

  The amidation reaction of carboxylic acid derivatives was developed using sulfur trioxide pyridine complex (SO3·py) as a commercially available and easily handled oxidant. This method could be applied to the reaction of various aromatic and aliphatic carboxylic acids, including optically active ones, with formamide derivatives to afford the corresponding amides in good to high yields.

  羧酸衍生物的酰胺化反应是使用三氧化硫吡啶配合物（SO3·py）作为市售且易于处理的氧化剂开发的。该方法可应用于各种芳香族和脂肪族羧酸，包括光学活性羧酸，与甲酰胺衍生物反应，以良好或高产率得到相应的酰胺。
• [EN] HETEROCYCLIC COMPOUNDS AND USES THEREOF<br/>[FR] COMPOSÉS HÉTÉROCYCLIQUES ET LEURS UTILISATIONS
  申请人：INFINITY PHARMACEUTICALS INC

  公开号：WO2013012918A1

  公开（公告）日：2013-01-24

  Compounds and pharmaceutical compositions of formulae (I), (XI) and (XII) as PI3 kinase modulators and their use in the treatment of diseases such as cancer.

  化合物和药物组合物的公式（I）、（XI）和（XII）作为PI3激酶调节剂，并在治疗癌症等疾病中的应用。
• Copper-Catalyzed Oxidative Coupling of Carboxylic Acids with<i>N</i>,<i>N</i>-Dialkylformamides: An Approach to the Synthesis of Amides
  作者：P. Santhosh Kumar、G. Sathish Kumar、R. Arun Kumar、N. Veera Reddy、K. Rajender Reddy

  DOI：10.1002/ejoc.201201544

  日期：2013.3

  A new synthetic approach for amide bond formation through the oxidative coupling of N,N-dialkylformamides with carboxylic acids was achieved by using a copper catalyst. Furthermore, this method was applied in the coupling of chiral amino acids in which the stereochemistry was retained in the resulting amide products.

  通过使用铜催化剂实现了通过 N,N-二烷基甲酰胺与羧酸的氧化偶联形成酰胺键的新合成方法。此外，该方法用于偶联手性氨基酸，其中立体化学保留在所得酰胺产物中。