6-苯甲酰基氨基-己酸 | 956-09-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 6-苯甲酰基氨基-己酸
• 英文名称: 6-(benzoylamino)hexanoic acid
• 英文别名: N-benzoyl-6-aminohexanoic acid；6-benzoylaminohexanoic acid；6-benzamidohexanoic acid；ε-benzamidocaproic acid；6-benzoylamino-n-caproic acid；6-benzoylamino-hexanoic acid
• CAS: 956-09-2
• 化学式: C₁₃H₁₇NO₃
• 分子量: 235.283
• InChiKey: LFCIOBCYMAQQBT-UHFFFAOYSA-N

物化性质

• 熔点：
  79 °C
• 沸点：
  488.4±28.0 °C(Predicted)
• 密度：
  1.136±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  66.4
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 海关编码：
  2924299090

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  ——	methyl 6-benzamidohexanoate	32039-15-9	C14H19NO3	249.31
  ——	N-benzoyl-ε-aminocapramide	84636-44-2	C13H18N2O2	234.298
  ——	N-(5-cyano-pentyl)-benzamide	642470-70-0	C13H16N2O	216.283
  ——	4-(benzoylamino)butanal	137521-24-5	C11H13NO2	191.23
  ——	Trimethylsilyl 6-benzamidohexanoate	1027184-41-3	C16H25NO3Si	307.465
  氮杂环庚-1-基-苯基甲酮	N-benzoyl-1H-hexahydroazepine	3653-39-2	C13H17NO	203.284

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  ——	methyl 6-benzamidohexanoate	32039-15-9	C14H19NO3	249.31
  ——	6-benzoylamino-hexanoic acid ethyl ester	198705-39-4	C15H21NO3	263.337
  DL-ω-苯甲酰赖氨酸	N6-benzoyl-lysine	5107-18-6	C13H18N2O3	250.298
  6-苯甲酰氨基-2-溴己酸	6-benzamido-2-bromohexanoic acid	1700-05-6	C13H16BrNO3	314.179
  6-苯酰胺-2-氯己酸	α-Chlor-ε-benzoylaminohexansaeure	5107-15-3	C13H16ClNO3	269.728
  N-戊基苯甲酰胺	N-pentylbenzamide	20308-43-4	C12H17NO	191.273
  N-苯甲酰基-1,5-二氨基戊烷	N-(5-aminopentyl)benzamide	5692-29-5	C12H18N2O	206.288
  ——	6-benzoylamino-hexanoic acid benzyl ester	102156-83-2	C20H23NO3	325.408
  ——	N-(6-oxo-6-phenylhexyl)benzamide	66727-88-6	C19H21NO2	295.381
  ——	N-benzyloxy-6-(4-benzoyl)aminocapramide	251456-93-6	C20H24N2O3	340.422

反应信息

• 作为反应物：
  描述：

  6-苯甲酰基氨基-己酸 在 lead(IV) acetate 、 碘 作用下， 以 四氯化碳 为溶剂， 生成 N-(5-Jod-pentyl)-benzamid
  参考文献：
  名称：

  445.光化学转化。第十七部分。酸脱羧的改进方法

  摘要：

  DOI：

  10.1039/jr9650002438
• 作为产物：
  描述：

  6-氨基己酸 在 sodium carbonate 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 生成 6-苯甲酰基氨基-己酸
  参考文献：
  名称：

  Studies Directed at the Use of a Parallel Synthesis Matrix to Increase Throughput in an in Vivo Assay

  摘要：

  Heparin is the anticoagulant of choice for hospitalized patients, but it is dosed only by injection because it is not absorbed following oral administration. We have discovered and prepared compounds (delivery agents) that facilitate the gastrointestinal absorption of heparin in rats, monkeys, and humans when given orally. We are currently developing a parallel synthesis approach to increase our delivery agent screening throughput in vivo. This approach has been used to produce micromolar quantities of compounds for testing in rats in a 5 x 5 parallel synthesis array. Using an amine benzoylation reaction sequence, 10 mixtures were prepared. These mixtures contained equal weight quantities of five N-substituted, non-alpha, amino acid delivery agents. Each of these mixtures was orally administered to rats in combination with heparin, and plasma clotting times (APTT) were measured to determine activity. Deconvolution of the data accurately identified the most active individual components. Independent synthesis of these compounds verified their activity. This parallel synthesis approach is an effective tool for the screening of oral heparin delivery agents and has increased screening throughput significantly.

  DOI：

  10.1021/jm990416r

文献信息

• PREPARATION OF<i>N</i>-ACYL DERIVATIVES OF AMINO ACIDS FROM ACYL CHLORIDES AND AMINO ACIDS IN THE PRESENCE OF CATIONIC SURFACTANTS. A VARIATION OF THE SCHOTTEN-BAUMANN METHOD OF BENZOYLATION OF AMINO ACIDS
  作者：Branko S. Jursic、Donna Neumann

  DOI：10.1081/scc-100000582

  日期：2001.1

  A very efficient method for the preparation of N-acylamino acids from the corresponding acyl chloride and amino acid is described. Amino acids, potassium carbonate, acyl chloride, and a catalytic amount of cationic surfactants were mixed in tetrahydrofuran and refluxed without ever obtaining a clear reaction mixture. After hot filtration, the product was isolated from the hot tetrahydrofuran solution

  描述了一种从相应的酰氯和氨基酸制备 N-酰基氨基酸的非常有效的方法。将氨基酸、碳酸钾、酰氯和催化量的阳离子表面活性剂混合在四氢呋喃中并回流，但从未获得澄清的反应混合物。热过滤后，产物以非常高或几乎定量的产率从热的四氢呋喃溶液中分离出来。
• Chemoselective Reductive Nucleophilic Addition to Tertiary Amides, Secondary Amides, and<i>N</i>-Methoxyamides
  作者：Minami Nakajima、Yukiko Oda、Takamasa Wada、Ryo Minamikawa、Kenji Shirokane、Takaaki Sato、Noritaka Chida

  DOI：10.1002/chem.201404648

  日期：2014.12.22

  modern organic synthesis, chemoselectivity is recognized as an important factor in the development of new methodologies. Chemoselective nucleophilic addition to amide carbonyl centers is a challenge because classical methods require harsh reaction conditions to overcome the poor electrophilicity of the amide carbonyl group. We have successfully developed a reductive nucleophilic addition of mild nucleophiles

  随着目标分子在现代有机合成中的复杂性增加，化学选择性被认为是开发新方法的重要因素。酰胺羰基中心的化学选择性亲核加成是一个挑战，因为经典方法需要苛刻的反应条件以克服酰胺羰基的不良亲电性。我们已经成功开发出使用Schwartz试剂将温和的亲核试剂还原性添加到叔酰胺，仲酰胺和N-甲氧基酰胺上的亲核试剂[Cp 2ZrHCl]。该反应在各种敏感的官能团，例如甲酯的存在下，以高度化学选择性的方式发生，这些官能团通常需要在亲核加成之前进行保护。该反应将适用于由容易获得的酰胺基团简单合成复杂的天然生物碱。
• Cross aldol condensation of acetaldehyde and formaldehyde in the presence of bifunctional systems
  作者：L. V. Dashko、D. V. Dmitriev、S. M. Pestov、V. R. Flid

  DOI：10.1134/s1070428014120021

  日期：2014.12

  Liquid-phase cross-aldol condensation of acetaldehyde and formaldehyde in the presence of salts of various saturated and unsaturated linear amines, aromatic amines, diamines, and nitrogen bases, as well as in the presence of substituted piperazines, linear and cyclic amino acids and their derivatives, and nitrogen-containing ionic liquids, was studied. The cross-condensation products were formed in

  在各种饱和和不饱和线性胺，芳族胺，二胺和氮碱的盐存在下，以及在取代的哌嗪，线性和环状氨基酸及其存在下，乙醛和甲醛的液相交叉羟醛缩合研究了其衍生物和含氮离子液体。当使用胺盐酸盐，N-苯甲酰基氨基酸和氨基酸酯作为催化剂时，形成大量的交叉缩合产物。盐和溶剂中氨基氮原子的碱性增加，有利于形成交叉缩合产物。
• Unique Oxidation Reaction of Amides with Pyridine-<i>N</i>-oxide Catalyzed by Ruthenium Porphyrin:  Direct Oxidative Conversion of <i>N</i>-Acyl-<scp>l</scp>-proline to <i>N</i>-Acyl-<scp>l</scp>-glutamate
  作者：Rina Ito、Naoki Umezawa、Tsunehiko Higuchi

  DOI：10.1021/ja045603f

  日期：2005.1.1

  Oxidations of alkanes, alkenes, and aromatic rings with pyridine N-oxides are efficiently catalyzed by ruthenium porphyrins under mild conditions. We show here that the oxidation of N-acyl cyclic amines with RuIVtetraarylporphyrin dichloride-2,6-substituted pyridine N-oxides directly gives N-acyl amino acids in modest to good yield via oxidative C-N bond cleavage. N-Acylpyrrolidines and N-acylpiperidines

  在温和的条件下，钌卟啉可以有效地催化烷烃、烯烃和芳环与吡啶 N-氧化物的氧化。我们在这里展示了 N-酰基环胺与 RuIVtetraarylporphyrin dichloride-2,6-取代的吡啶 N-氧化物的氧化直接通过氧化 CN 键裂解以适度到良好的产率得到 N-酰基氨基酸。N-酰基吡咯烷和N-酰基哌啶分别转化为N-酰基-γ-氨基丁酸和N-酰基-δ-氨基戊酸。这种类型的反应是一种新颖的反应，其中 CN 键在较少取代的碳上被选择性地裂解。值得注意的是，含脯氨酸肽中的脯氨酸残基被选择性地转化为谷氨酸。在 N-苯甲酰基 [2,2,-d2] 吡咯烷的氧化中观察到了较大的分子内动力学同位素效应 (kH/kD = 9.8)，表明该反应应涉及作为速率决定步骤的 α-氢原子提取过程。N-酰基甲醛是α-羟基化N-酰基环胺的假定中间体开环形式，很容易用氧化系统氧化，以良好的产率得到相应的N-酰基氨基酸。
• Carbamic acid compounds comprising an amide linkage as hdac inhibitors
  申请人：——

  公开号：US20040092598A1

  公开（公告）日：2004-05-13

  This invention pertains to certain active carbamic acid compounds which inhibit HDAC activity and which have the formula (1) wherein: A is an aryl group; Q1 is an aryl leader group having a backbone of at least 2 carbon atoms; J is an amide linkage selected from: —NR1C(═O)—and —C(═O)NR1—; R1 is an amido substituent; and, Q2 is an acid leader group; and pharmaceutically acceptable salts, solvates, amides, esters, ethers, chemically protected forms, and prodrugs thereof. The present invention also pertains to pharmaceutical compositions comprising such compounds, and the use of such compounds and compositions, both in vitro and in vivo, to inhibit HDAC, and, e.g., to inhibit proliferative conditions, such as cancer and psoriasis.

  这项发明涉及抑制HDAC活性的某些活性碳酸酰胺化合物，其化学式为（1），其中：A是芳基；Q1是至少有2个碳原子骨架的芳基前导基团；J是选择自以下的酰胺键：—NR1C(═O)—和—C(═O)NR1—；R1是酰胺取代基；Q2是酸前导基团；以及其药学上可接受的盐、溶剂化合物、酰胺、酯、醚、化学保护形式和前药。本发明还涉及包含这种化合物的药物组合物，以及在体外和体内使用这种化合物和组合物来抑制HDAC，例如，抑制增殖性疾病，如癌症和牛皮癣。