4-(4-氨基苯)丁酸甲酯 | 20637-09-6

• 物质功能分类: 化学试剂 - 有机试剂 - 酯类
• 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: 4-(4-氨基苯)丁酸甲酯
• 中文别名: 4-(对氨基苯)丁酸甲酯；4-氨苯基丁酸甲酯；对氨基苯丁酸甲酯
• 英文名称: methyl 4-(4-aminophenyl)butanoate
• 英文别名: methyl 4-(4-aminophenyl)butyrate
• CAS: 20637-09-6
• 化学式: C₁₁H₁₅NO₂
• mdl: MFCD07366753
• 分子量: 193.246
• InChiKey: CLKHQWJXESOLCJ-UHFFFAOYSA-N

物化性质

• 熔点：
  42 °C(Solv: ligroine (8032-32-4))
• 沸点：
  323.9±25.0 °C(Predicted)
• 密度：
  1.088±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.363
• 拓扑面积：
  52.3
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2922499990
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335
• 储存条件：
  2-8℃

制备方法与用途

化学性质：针状晶体，熔点为42℃。

用途：作为有机化工原料中间体。

生产方法：由4-(对氨基苯)丁酸与甲醇酯化而得。具体步骤如下：在干燥的反应锅中加入甲醇并搅拌，然后分批加入对氨基苯丁酸和氯化氢甲醇溶液，加热回流3小时。随后减压回收甲醇至干，析出甲酯盐酸盐。将该物质加冰水溶解，再用活性炭脱色并过滤。最后，使用氢氧化钠溶液调节pH值至8，即可析出4-(对氨基苯)丁酸甲酯沉淀。

反应信息

• 作为反应物：
  描述：

  4-(4-氨基苯)丁酸甲酯 在 盐酸 、 溶剂黄146 、 三氯氧磷 作用下， 以 甲苯 为溶剂， 生成 苯丁酸氮芥
  参考文献：
  名称：

  Synthesis and pharmacokinetic profile of a quaternary ammonium derivative of chlorambucil, a potential anticancer drug for the chemotherapy of chondrosarcoma

  摘要：

  As a part of our targeting program based on the affinity of the quaternary ammonium moiety for cartilage, our objective was to develop more selective anticancer drugs towards chondrosarcoma that would concentrate in this malignant cartilaginous tissue and so improve the therapeutic index through a reduction of side effects. For this purpose we have synthesized and labeled with C-14 a quaternary ammonium (QA) derivative of chlorambucil. Biological studies performed in rats showed that [C-14]-CQA and [C-14]-chlorambucil exhibited different pharmacokinetic profiles. The blood elimination of [C-14]-CQA was faster than that of parent compound. [C-14]-CQA was principally excreted by the fecal way. However, until 15 min after administration, levels of radioactivity were measured in cartilaginous tissues of rats given [C-14]-CQA which was not the case for the rats which had received [C-14]-chlorambucil. Although rates of radioactivity were quantified only during 15 min, these results prove that the functionalization of chlorambucil by a quaternary ammonium group allows the molecule to be carried selectively to cartilaginous tissues. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2003.09.006
• 作为产物：
  描述：

  3-(4-乙酰基氨基苯甲酰基)丙酸 在 palladium on activated charcoal 硫酸 、 sulfur tetrafluoride 、 氢氟酸 、 氢气 、 双氧水 、 三氟乙酸酐 作用下， 以 甲醇 、 二氯甲烷 、 溶剂黄146 为溶剂， 反应 28.25h， 生成 4-(4-氨基苯)丁酸甲酯
  参考文献：
  名称：

  4 [3'-双（2”-氯乙基）氨基苯基] -4,4-二氟丁酸[4,4-二氟-间氯苯丁酸]的合成

  摘要：

  制备4- [4'-双（2”-氯乙基）氨基苯基] -4,4-二氟丁酸{4,4-二氟氯丁酸}的合成序列没有超出涉及甲基4,4-二氟-4的中间阶段-（4'-氨基苯基）丁酸酯，因为该胺是水解不稳定的。4-（3'-硝基苯基）-4-氧代丁酸甲酯与四氟化硫反应，然后加氢氢化，得到稳定的异构体4,4-二氟-4-（3'-氨基苯基）丁酸甲酯。通过环氧乙烷处理进行双羟乙基化，通过Ph 3 P / CCL 4将OH转化为Cl ，然后酯基水解，得到4- [3'-双（2″-氯乙基）氨基苯基] -4,4 -二氟丁酸，4-二氟间氯苯丁酸

  DOI：

  10.1016/s0022-1139(97)00070-5

文献信息

• Novel, Cyclically Substituted Furopyrimidine Derivatives and Use Thereof
  申请人：Lampe Thomas

  公开号：US20110124665A1

  公开（公告）日：2011-05-26

  The present application relates to novel, cyclically substituted furopyrimidine derivatives, methods for their production, their use for the treatment and/or prophylaxis of diseases and their use for the production of medicinal products for the treatment and/or prophylaxis of diseases, in particular for the treatment and/or prophylaxis of cardiovascular diseases.

  本申请涉及新型的、环状取代的呋喃嘧啶衍生物，其生产方法，以及它们用于治疗和/或预防疾病的应用，特别用于治疗和/或预防心血管疾病的治疗和/或预防药物的生产。
• 一种苯丁酸氮芥衍生物的制备方法
  申请人：梯尔希（南京）药物研发有限公司

  公开号：CN105859570A

  公开（公告）日：2016-08-17

  本发明公开了一种苯丁酸氮芥衍生物的制备方法，该方法以4‑(对氨基苯)丁酸甲酯为起始原料，经六步反应合成得到苯丁酸氮芥衍生物。本发明通过大量实验筛选出最优的制备步骤和反应条件，整个工艺设计合理，可操作性强，提纯方便。本发明制备得到的苯丁酸氮芥衍生物，纯度可达99％以上，总收率可达50％以上。制备得到的苯丁酸氮芥衍生物，可广泛用于全面分析苯丁酸氮芥的药理，药代，毒理等试验。
• Benzamide compounds as apo b secretion inhibitors
  申请人：——

  公开号：US20040058903A1

  公开（公告）日：2004-03-25

  The present invention relates to compounds of the formula (I) wherein R 1 and R 2 are each independently lower alkyl lower alkenyl, acyl, amino, lower alkoxy, lower cycloalkyloxy, aryl, aryloxy, sulfooxy, mercapto, sulfo, hydrogen, halogen, nitro, cyano or hydroxy, or may form a ring structure; Q 1 is N or CH; L is optionally substituted unsaturated 3 to 10-membered heterocyclic group; X is optionally substituted monocyclic arylene or monocyclic heteroarylene; Y is -(A 1 ) m -(A 2 ) n -(A 4 ) k -; Z is directbond, —CH2-, —NH— or —O—; and R is hydrogen or lower alkyl, or a salt thereof The compounds of the present invention inhibit apolipoprotein B (Apo B) secretion and are useful as a medicament for prophylactic and treatment of diseases or conditions resulting from elevated circulating levels of Apo B.

  本发明涉及式(I)的化合物，其中R1和R2分别独立地为较低的烷基较低的烯基、酰基、氨基、较低的烷氧基、较低的环烷氧基、芳基、芳氧基、磺氧基、巯基、磺基、氢、卤素、硝基、氰基或羟基，或者可以形成环结构；Q1为N或CH；L是可选的取代的不饱和的3到10元杂环基；X是可选的取代的单环芳基或单环杂芳基；Y是-(A1)m-(A2)n-(A4)k-；Z是直键，-CH2-，-NH-或-O-；R为氢或较低的烷基，或其盐。本发明的化合物抑制载脂蛋白B（Apo B）的分泌，并可用作预防和治疗由于载脂蛋白B循环水平升高而导致的疾病或症状的药物。
• Oxadiazole derivatives as S1P1 receptor agonists
  申请人：Almirall, S.A.

  公开号：EP2210890A1

  公开（公告）日：2010-07-28

  New compounds having the chemical structure of formula (I) or pharmaceutically acceptable salts or N-oxides thereof wherein A is selected from the group consisting of -N-, -O- and -S-; B and C independently are selected from the group consisting of -N- and -O-, with the proviso that at least two of A, B and C are nitrogen atoms; G1 is selected from the group consisting of nitrogen atoms and -CRC- groups, wherein RC represents a hydrogen atom, a halogen atom, a C1-4 alkyl group or a C1-4 alkoxy group; R1 is selected from the group consisting of hydrogen atoms, C1-4 alkyl groups, C1-4 alkoxy groups, C3-4 cycloalkyl groups, and -NRdRe groups wherein Rd and Re are independently selected from hydrogen atoms and C1-4 alkyl groups; R2 and R3 are independently selected from the group consisting of hydrogen atoms and C1-4 alkyl groups; R4, R5 and R7 are independently selected from the group consisting of hydrogen atoms, halogen atoms, C1-4 alkyl groups, C1-4 alkoxy groups and C1-4 haloalkyl groups; R6 represents a C1-4 alkyl group or a C1-4 hydroxyalkyl group; or R6 is selected from the group consisting of -S(O)2-NRaRb groups, -(CRfRg)n-(CRhRi)x-(CRjRk)y-NRaRb groups, -(CH2)n-NRaRb groups, -O-(CH2)n-NRaRb groups, -(CH2)n-COOH groups, -(CH2)n-NRa-CO-Rb' groups, -(CH2)n-NRa-(CH2)p-(NH)q-SO-CH3 groups and -(CH2)n-CO-NRaRb groups, wherein n, p, x and y are each independently integers from 0 to 3, q is 0 or 1, Rf, Rg, Rh, Ri, Rj and Rk independently represent hydrogen atoms or halogen atoms, Rb' is selected from the group consisting of methylsulphonyl groups, C1-4 alkyl groups, C1-4 hydroxyalkyl groups, C1-4 carboxyalkyl groups, and C1-4 haloalkyl groups; Ra and Rb are independently selected from the group consisting of hydrogen atoms, methylsulphonyl groups, C1-4 alkyl groups, C1-4 hydroxyalkyl groups, C1-4 carboxyalkyl groups, and C1-4 haloalkyl groups, or Ra and Rb together with the nitrogen atom to which they are attached form a 4 to 6 membered, saturated heterocyclic group, which contains, as heteroatoms, one or two nitrogen atoms and which is substituted by a carboxyl group or a C1-4 carboxyalkyl group; or Rc together with R6 form a C5-8 carbocyclic ring optionally substituted by - NHR' wherein R' represents a hydrogen atom or a 61-4 carboxyalkyl group.

  新化合物具有化学结构的公式(I)或其药学上可接受的盐或N-氧化物，其中 A选自由-N-，-O-和-S-组; B和C独立地选自- N-和-O-组，但至少两个A，B和C是氮原子; G1选自氮原子和-CRC-基团组，其中RC代表氢原子，卤素原子，C1-4烷基基团或C1-4烷氧基团; R1选自氢原子，C1-4烷基基团，C1-4烷氧基团，C3-4环烷基基团和-NRdRe基团，其中Rd和Re独立地选自氢原子和C1-4烷基基团; R2和R3独立地选自氢原子和C1-4烷基基团; R4，R5和R7独立地选自氢原子，卤素原子，C1-4烷基基团，C1-4烷氧基团和C1-4卤代烷基基团; R6代表C1-4烷基基团或C1-4羟基烷基基团; 或R6选自-S(O)2-NRaRb基团，-(CRfRg)n-(CRhRi)x-(CRjRk)y-NRaRb基团， -(CH2)n-NRaRb基团，-O-(CH2)n-NRaRb基团，-(CH2)n-COOH基团，-(CH2)n-NRa-CO-Rb'基团，-(CH2)n-NRa-(CH2)p-(NH)q-SO-CH3基团和-(CH2)n-CO-NRaRb基团，其中 n，p，x和y分别独立地为0到3的整数， q为0或1， Rf，Rg，Rh，Ri，Rj和Rk独立地代表氢原子或卤素原子， Rb'选自甲磺酰基团，C1-4烷基基团，C1-4羟基烷基基团，C1-4羧基烷基基团和C1-4卤代烷基基团组; Ra和Rb独立地选自氢原子，甲磺酰基团，C1-4烷基基团，C1-4羟基烷基基团，C1-4羧基烷基基团和C1-4卤代烷基基团，或 Ra和Rb与它们连接的氮原子一起形成一个含有4到6个成员的饱和杂环基团，其中作为杂原子，含有一个或两个氮原子，并且被羧基或C1-4羧基烷基基团取代; 或 Rc与R6一起形成一个C5-8碳环戊环，可选择地被-NHR'取代，其中R'代表氢原子或C1-4羧基烷基基团。
• Design and synthesis of sialyl lewis x mimics as e-selectin inhibitors
  作者：Neelu Kaila、Bert E. Thomas、Paresh Thakker、Juan C. Alvarez、Raymond T. Camphausen、Deidre Crommie

  DOI：10.1016/s0960-894x(00)00623-5

  日期：2001.1

  The design and synthesis of novel beta-C-mannosides that inhibit the binding of sialyl Lewis x to E-selectin are described. Compounds that contained a phenyl substituent at the C-6 position were found to have increased potency.

  描述了抑制唾液酸路易斯x与E-选择素结合的新型β-C-甘露糖苷的设计和合成。发现在C-6位上含有苯基取代基的化合物具有增强的效力。

表征谱图