N-benzoylaspartic acid | 17966-68-6

• 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-benzoylaspartic acid
• 英文别名: N-benzoyl-D,L-aspartic acid；DL-N-benzoylaspartic acid；N-Benzoyl aspartic acid；N-benzoyl-aspartic acid；N-Benzoyl-DL-asparaginsaeure；N-Benzoyl-asparaginsaeure；2-benzamidobutanedioic acid
• CAS: 17966-68-6
• 化学式: C₁₁H₁₁NO₅
• 分子量: 237.212
• InChiKey: DJLTZJGULPLVOA-UHFFFAOYSA-N

物化性质

• 熔点：
  174 °C
• 沸点：
  502.0±40.0 °C(Predicted)
• 密度：
  1.404±0.06 g/cm3(Predicted)
• 物理描述：
  Solid

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  104
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-benzoylaspartic acid 在 盐酸 作用下， 生成 DL-天门冬氨酸
  参考文献：
  名称：

  dl-天冬氨酸的新合成。

  摘要：

  DOI：

  10.1021/ja01199a032
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 potassium permanganate 、 硫酸 、 水 作用下， 生成 N-benzoylaspartic acid
  参考文献：
  名称：

  诺瓦林斯

  摘要：

  DOI：

  10.1002/hlca.19300130610

文献信息

• Brine-Mediated Efficient Benzoylation of Primary Amines and Amino Acids
  作者：Gautam Chattopadhyay、Suchandra Chakraborty、Chandan Saha

  DOI：10.1080/00397910802250929

  日期：2008.11.3

  Abstract Benzoylation of primary amines and amino acids is efficiently carried out in a brine solution using a stoichiometric amount of benzoyl chloride followed by trituration with aqueous saturated bicarbonate solution.

  摘要 伯胺和氨基酸的苯甲酰化在盐水溶液中使用化学计量的苯甲酰氯有效地进行，然后用饱和碳酸氢盐水溶液研磨。
• Method for producing chiral mercapto amino acids
  申请人：Kotthaus Martina

  公开号：US20070112216A1

  公开（公告）日：2007-05-17

  The invention relates to a method for producing chiral mercapto amino acids of formula (I) wherein R 1 , R 2 and R 3 can represent hydrogen, C 6 -C 12 aryl, C 1 -C 6 -alkyl-C 6 -C 12 -aryl, C 6 -C 12 -aryl-C 1 -C 6 -alkyl, C 1 -C 18 -alkyl or C 2 -C 18 -alkenyl, R 2 and R 3 forming a saturated or unsaturated ring. According to said method, a) an oxo compound of formula (II), wherein X represents a leaving group, is reacted in the presence of ammonia or ammonium hydroxide and a sulfide, optionally under phase transfer catalysis or addition of a solubiliser, with a ketone or an aldehyde of formula (III) wherein R 4 and R 5 can represent a C 1 -C 12 alkyl radical or a C 6 -C 20 aryl radical or one of the two radicals H, or R 4 and R 5 together form a C 4 -C 7 ring, to form the compound of formula (IV), that b) reacts with HCN to form the corresponding nitrile, whereupon c) the crystallised nitrile is converted, by selective hydrolysis by means of a mineral acid, into the corresponding amide of formula (VI), and d) is then converted into the corresponding chiral amide of formula (VI*) by means of an L amidase or a chiral dissociating acid, whereupon by reaction with an acid, the desired chiral mercapto amino acid of formula (I) is obtained, or e) first the reaction with an acid is carried out, and then the conversion into the chiral mercapto amino acid takes place.

  该发明涉及一种生产手性巯基氨基酸的方法，其化学式为(I)，其中R1、R2和R3可以代表氢、C6-C12芳基、C1-C6烷基-C6-C12芳基、C6-C12芳基-C1-C6烷基、C1-C18烷基或C2-C18烯基，R2和R3形成饱和或不饱和环。根据该方法，a）在氨或氢氧化铵存在下，将具有化学式(II)的羰基化合物，其中X代表离去基团，与具有化学式(III)的酮或醛反应，其中R4和R5可以代表C1-C12烷基基团或C6-C20芳基基团或两个基团H中的一个，或者R4和R5一起形成C4-C7环，形成具有化学式(IV)的化合物，然后b）与HCN反应形成相应的腈，随后c）通过矿酸的选择性水解将结晶的腈转化为具有化学式(VI)的相应酰胺，并且d）通过L-酰胺酶或手性分离酸将其转化为具有化学式(VI*)的相应手性酰胺，然后通过与酸的反应得到所需的手性巯基氨基酸，或者e）首先进行与酸的反应，然后进行转化为手性巯基氨基酸。
• [EN] POTENT INHIBITORS OF ASPARTATE N-ACETYL-TRANSFERASE FOR THE TREATMENT OF CANAVAN DISEASE<br/>[FR] INHIBITEURS PUISSANTS DE L'ASPARTATE N-ACÉTYL-TRANSFÉRASE POUR LE TRAITEMENT DE LA MALADIE DE CANAVAN
  申请人：UNIV TOLEDO

  公开号：WO2017172476A1

  公开（公告）日：2017-10-05

  Compounds, compositions, and methods for the treatment of Canavan disease are described.

  描述了用于治疗卡纳万病的化合物、组合物和方法。
• Method for producing optical-active cis-piperidine derivatives
  申请人：——

  公开号：US20040171836A1

  公开（公告）日：2004-09-02

  An optical-active cis-piperidine derivative of high chemical purity and high optical purity is efficiently produced through optical resolution of a cis-piperidine derivative mixture, racemic cis-piperidine derivative with an optical-active tartaric acid derivative or an optical-active amino acid derivative. For the optical-active tartaric acid derivative, preferred are optical-active di(paratoluoyl)tartaric acid and optical-active di(4-methoxybenzoyl)tartaric acid; and for the optical-active amino acid derivative, preferred is optical-active N-benzenesulfonylphenylalanine.

  高化学纯度和高光学纯度的光学活性顺式哌啶衍生物可通过对顺式哌啶衍生物混合物进行光学分辨得到，所述混合物包括光学活性酒石酸衍生物或光学活性氨基酸衍生物与混合的顺式哌啶衍生物，所述混合的顺式哌啶衍生物为消旋的。对于光学活性酒石酸衍生物，首选的是光学活性二(对甲苯基)酒石酸和光学活性二(4-甲氧基苯甲酰)酒石酸；对于光学活性氨基酸衍生物，首选的是光学活性N-苯磺酰苯丙氨酸。
• [EN] NEW POSSIBILITIES OF CHIRAL RESOLUTION OF BEDAQUILINE<br/>[FR] NOUVELLES POSSIBILITÉS DE RÉSOLUTION CHIRALE DE LA BÉDAQUILINE
  申请人：ZENTIVA KS

  公开号：WO2016116076A1

  公开（公告）日：2016-07-28

  A method of performing isolation and purification of bedaquiline (la) from a mixture of stereoisomers of 6-bromo-2-methoxy-quinolin-3 -yl)-4-dimethylamino-2-( 1 -naphthyl)- 1 - phenyl-butan-2-ol identified as I-rac, being a mixture of the stereoisomers of formulae la, lb, and Il-rac, being a mixture of the stereoisomers of formulae Ila, lib, with any ratio of individual constituents of the mixture, wherein said mixture is dissolved together with derivatives of N-benzoyl-L-aspartic acid Ilia, wherein R1 and R2 independently stand for hydrogen, a primary, secondary or tertiary C1-C4 alkyl, a primary or secondary amide, wherein always at least one of the R1 or R2 symbols stands for hydrogen; and R3 is a C5-C12 aryl, C5-C12 heteroaryl with one or more heteroatoms, which may be further substituted by a halogen, amino group, carbonyl, or carboxyl, or its functional derivative, preferably phenyl, naphthyl, tolyl, or mesytyl, and the resulting salt is recrystallized from a suitable solvent or mixture, which can be ketones, esters, ethers, amides, nitriles or organic acids, alcohols, aliphatic and aromatic hydrocarbons, chlorinated hydrocarbons, water and/or their mixtures.

  一种从6-溴-2-甲氧基喹啉-3-基)-4-二甲基氨基-2-(1-萘基)-1-苯基-丁-2-醇的立体异构体混合物中分离和纯化bedaquiline (la)的方法，其被鉴定为I-rac混合物，包含式la、lb的立体异构体混合物和Il-rac混合物，包含式Ila、lib的立体异构体混合物，其中混合物的各个成分的比例任意，所述混合物与N-苯甲酰-L-天冬氨酸衍生物Ilia一起溶解，其中R1和R2独立地代表氢、一级、二级或三级C1-C4烷基、一级或二级酰胺，其中至少一个R1或R2符号始终代表氢；而R3是C5-C12芳基、C5-C12杂环芳基，带有一个或多个杂原子，可以进一步被卤素、氨基、羰基或羧基取代，或其官能衍生物，优选苯基、萘基、甲苯基或甲基苯基，然后从适当的溶剂或混合物中，可以是酮、酯、醚、酰胺、腈或有机酸、醇、脂肪族和芳香族碳氢化合物、氯化碳氢化合物、水和/或它们的混合物中重新结晶得到所述盐。