2-[2-(3-甲氧基苯基)乙基]苯甲酸 | 17910-71-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 中文名称: 2-[2-(3-甲氧基苯基)乙基]苯甲酸
• 英文名称: 2-(m-methoxyphenethyl)benzoic acid
• 英文别名: 2-[2-(3-methoxyphenyl)ethyl]benzoic Acid
• CAS: 17910-71-3
• 化学式: C₁₆H₁₆O₃
• 分子量: 256.301
• InChiKey: GYAQJSPEJNXRQE-UHFFFAOYSA-N

物化性质

• 熔点：
  116.8-119 °C
• 沸点：
  396.4±22.0 °C(Predicted)
• 密度：
  1.167±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 危险等级：
  IRRITANT

反应信息

• 作为反应物：
  描述：

  2-[2-(3-甲氧基苯基)乙基]苯甲酸 在 sodium hydroxide 、 N-溴代丁二酰亚胺(NBS) 、 三氯化铝 、 TEA 、 potassium tert-butylate 作用下， 以 1,4-二氧六环 、 四氯化碳 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 65.91h， 生成 5-<(5-Oxo-dibenzocyclohepten-2-yl)oxy>valeric acid
  参考文献：
  名称：

  Synthesis of 5-(((R,S)-5-((9-Fluorenylmethoxycarbonyl)amino)-10,11-dihydrodibenzo[a,d]cyclohepten-2-yl)oxy)valeric Acid (CHA) and 5-(((R,S)-5-((9-Fluorenylmethoxycarbonyl)amino)dibenzo[a,d]-cyclohepten-2-yl)oxy)valeric Acid (CHE) Handles for the Solid-Phase Synthesis of C-Terminal Peptide Amides under Mild Conditions

  摘要：

  Two novel handles for peptide amide preparation under mild conditions were developed for use in highly efficient solid-phase peptide synthesis. These handles, 5-{[(R,S)-5-[(9-fluorenylmethoxy-carbonyl)amino]-10,11-dihydrodibenzo[a,d]cyclohepten-2-yl]oxy}valeric acid (CHA) and 5-{[(R,S)-5-[(9-fluorenylmethoxycarbonyl)amino]dibenzo[a,d]cyclohepten-2-yl]oxy}valeric acid (CHE), were attached to the solid support and were used for syntheses of peptides having a C-terminal amide by the fluorenylmethoxycarbonyl strategy. The cleavability of CHA and CHE was determined and compared with the that commercially available amide handles. CHA and CHE handles can be rapidly cleaved from the polymer support without significant side reactions using lower acid concentrations than those required for conventional handles. As CHA can be easily synthesized in large amounts, it is suitable for peptide amide preparation for pharmaceuticals. As CHE can be cleaved at very low concentrations of acid, it is especially suitable for preparing side chain-protected peptide amides: Several brain-gut peptides having a C-terminal amide were synthesized in high yield and high purity with these novel handles.

  DOI：

  10.1021/jo00105a010
• 作为产物：
  描述：

  2-溴甲基苯甲酸甲酯 在 palladium on activated charcoal sodium hydroxide 、 氢气 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 1,4-二氧六环 、 甲醇 为溶剂， 反应 0.75h， 生成 2-[2-(3-甲氧基苯基)乙基]苯甲酸
  参考文献：
  名称：

  用于固相肽合成的通用接头的设计：C末端伯/仲酰胺和酰肼的合成

  摘要：

  已经开发了基于二苯并环庚-1,4-二烯系统的高效，多功能的固相肽合成接头，用于合成C端伯/仲酰胺和酰肼。

  DOI：

  10.1016/0040-4039(93)88115-y

文献信息

• Facile Synthesis of 3-Methoxy-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-one: Application to the Acid-Labile Peptide Amide Linker Containing the 10,11-Dihydro-5H-dibenzo[a,d]cycloheptene Moiety.
  作者：Masaki NODA

  DOI：10.1248/cpb.46.1157

  日期：——

  The facile synthesis of 3-methoxy-10, 11-dihydro-5H-dibenzo[a, d]cyclohepten-5-one (5) via m-methoxystilbene-2-carboxylic acid (3) was developed for the preparation of the mild acid labile peptide amide linker containing 10, 11-dihydro-5H-dibenzo[a, d]cyclohepten-5-yl group for Fmoc (9-Fluorenylmethoxycarbonyl)-solid phase peptide synthesis.

  简单合成了3-甲氧基-10, 11-二氢-5H-二苯并[a, d]环庚烯-5-酮（5），通过m-甲氧基芪-2-羧酸（3）制备含有10, 11-二氢-5H-二苯并[a, d]环庚烯-5-基团的温和酸易裂解肽酰胺连接剂，用于Fmoc（9-芴甲氧羰基）固相肽合成。
• 5-Alkyl or hydroxyalkyl
  申请人：Merck & Co., Inc.

  公开号：US04399141A1

  公开（公告）日：1983-08-16

  5-Substituted-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5,10-imines, derivatives and pharmaceutically acceptable salts thereof are useful as anticonvulsants.

  5-取代-10,11-二氢-5H-二苯并[a,d]环庚烯-5,10-亚胺及其衍生物和药用盐可用作抗癫痫药。
• Tricyclic triarylethylene antiestrogens: dibenz[b,f]oxepins, dibenzo[b,f]thiepins, dibenzo[a,e]cyclooctenes, and dibenzo[b,f]thiocins
  作者：David Acton、George Hill、Brian S. Tait

  DOI：10.1021/jm00362a009

  日期：1983.8

  potent compounds were 3-[2-(dimethylamino)ethoxy] -10-ethyl-11-(4-hydroxyphenyl)dibenzo[b,f]thiepin (7b) and 3-[2-(dimethylamino)ethoxy]-11-ethyl-12-(4-hydroxyphenyl)-5,6-dihydrodibenzo[a,e]-cyclooctene (7c), which had good binding (approximately 50% relative to estradiol) and good antiestrogenic activity (ca. one-half of the potency of tamoxifen, III). In this series, the O-bridged compound was the

  桥接基团O，S，CH2CH2和SCH2用于生产一系列26个三环三芳基乙烯。在竞争结合试验中测量了它们与大鼠子宫雌激素受体的体外结合。大鼠的抗生育和子宫营养测试表明存在抗雌激素活性。最有趣的系列有一个基本侧链，最有效的化合物是3- [2-（二甲基氨基）乙氧基] -10-乙基-11-（4-羟基苯基）二苯并[b，f]噻吩（7b）和3 -[2-（二甲基氨基）乙氧基] -11-乙基-12-（4-羟基苯基）-5,6-二氢二苯并[a，e]-环辛烯（7c），具有良好的结合力（相对于雌二醇约为50％）和良好的抗雌激素活性（约为他莫昔芬（Ⅲ）药效的一半）。在本系列中，O桥化合物的活性最低，这是用二苯并二甲苯环系统的平面度来解释的。在某些化合物中发现了镇静活性。
• Tricyclic antidepressant derivatives and immunoassay
  申请人：Roche Diagnostics Corporation

  公开号：US06368814B1

  公开（公告）日：2002-04-09

  The present invention is directed to novel tricyclic antidepressant drug derivatives synthesized for covalent attachment to proteins or polypeptide antigens for use in the preparation of antibodies or receptors to tricyclic antidepressant drugs and tricyclic antidepressant metabolites. The new derivatives are characterized by a saturated double bond on the amitriptyline portion of the molecule and are represented by the structure where R1 is a saturated or unsaturated, substituted or unsubstituted, straight or branched chain of 0-10 carbon or heteroatoms, X is a linker group consisting of 0-2 substituted or unsubstituted aromatic rings, and Y is an activated ester or NH—Z, where Z is a poly(amino acid). The novel tricyclic antidepressant activated hapten derivatives are useful for preparing tracers and conjugates for tricyclic antidepressant immunoassays, including an enzyme immunoassay and a microparticle capture inhibition assay using an antibody produced from the novel immunogen with a conjugate derivatized either at the N-1 position of imipramine or at the C-2 position of dihydroamitriptyline.

  本发明涉及一种新型三环抗抑郁药物衍生物，该衍生物经合成可共价连接到蛋白质或多肽抗原上，用于制备抗体或受体以对抗三环抗抑郁药物和三环抗抑郁药物代谢物。新的衍生物的特点是分子中的阿米替林部分具有饱和双键，其结构表示为R1是0-10碳或杂原子的饱和或不饱和、取代或未取代的直链或支链，X是由0-2个取代或未取代的芳香环组成的连接基团，Y是活性酯或NH-Z，其中Z是多肽（氨基酸）。这种新型三环抗抑郁药物活化半抗原衍生物可用于制备三环抗抑郁药物免疫分析的示踪剂和结合物，包括使用从新型免疫原产生的抗体制备的酶免疫分析和微粒捕获抑制分析，其中结合物在氨替林的N-1位置或二氢阿米替林的C-2位置衍生化。
• (R,S)-2-[[5-(9-芴甲氧羰基氨基)二苯并[a,d]环 庚烷-2-基]氧]乙酸的制备方法
  申请人：吉尔生化（上海）有限公司

  公开号：CN104761470B

  公开（公告）日：2016-08-24

  本发明涉及Ramage linker的制备方法，主要解决原合成方法步骤长，后处理麻烦，三废多，成本高的技术问题。制备由A.邻羧基苯甲醛和间甲氧基苯乙酸反应得到中间体2‑（3‑甲氧基苯乙烯基）苯甲酸,中间体用溶剂溶解，然后氢化还原，再后处理结晶得到R‑1；B.（R‑1）与SOCl2或POCl3反应得到2‑甲氧基‑10,11‑二氢‑5H‑二苯并[a,d]环庚烷‑5‑酮,负压蒸去SOCl2或POCl3后，用苯、甲苯或1,2‑二氯乙烷溶解，在无水AlCl3的催化反应后处理结晶得到R‑2；C.(R‑2）在DMF或丙酮碳酸钾溶液中和溴乙酸苄酯反应生成R‑3；D．(R‑3）氢化还原得到R‑4；E.（R‑4）在DMF中加入催化剂量的PTS,和Fmoc‑NH2反应得到Remage linker。Ramage linker是一种有效的固相合成C‑端链接剂。