2-(4-溴苄基)丙烯酸 | 860256-21-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 苯丙酸
• 中文名称: 2-(4-溴苄基)丙烯酸
• 英文名称: 2-(4-bromobenzyl)acrylic acid
• 英文别名: 2-(4-Brom-benzyl)-acrylsaeure；2-(p-bromobenzyl)acrylic acid；2-[(4-Bromophenyl)methyl]prop-2-enoic acid
• CAS: 860256-21-9
• 化学式: C₁₀H₉BrO₂
• 分子量: 241.084
• InChiKey: SKAPNLGQSOPINP-UHFFFAOYSA-N

物化性质

• 熔点：
  119 °C
• 沸点：
  386.7±30.0 °C(Predicted)
• 密度：
  1.497±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(4-溴苄基)丙烯酸 在 TEA 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 作用下， 以 二氯甲烷 为溶剂， 反应 2.5h， 生成 (S)-2-[2-Acetylsulfanylmethyl-3-(4-bromo-phenyl)-propionylamino]-3-(1H-indol-3-yl)-propionic acid ethyl ester
  参考文献：
  名称：

  Thiol inhibitors of endothelin-converting enzyme

  摘要：

  Synthesis and structure activity relationships of a series of thiol inhibitors of the endothelin-converting enzyme (ECE) are presented. Optimisation of the stereochemistry as well as of the P'(1) and P'(2) residues led to inhibitors with similar potency to that of phosphoramidon. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0960-894x(96)00420-9
• 作为产物：
  描述：

  1-溴-4-(碘甲基)苯 在 sodium hydride 、 potassium carbonate 、 lithium hydroxide 作用下， 以 四氢呋喃 、 水 、 二甲基亚砜 、 mineral oil 为溶剂， 反应 4.5h， 生成 2-(4-溴苄基)丙烯酸
  参考文献：
  名称：

  Rhodium(iii)-catalyzed C–H allylation of electron-deficient alkenes with allyl acetates

  摘要：

  铑催化的C-H烯丙基化反应报道了使用各种烯丙醋酸酯对丙烯酰胺衍生物进行反应。使用弱配位导向基团导致高反应效率和优异的γ-选择性。该反应显示出广泛的官能团容忍性，为获得官能化的1,4-二烯骨架开辟了新的合成途径。

  DOI：

  10.1039/c4cc07597h

文献信息

• Microwave-assisted synthesis of the (E)-α-methylalkenoate framework from multifunctionalized allylic phosphonium salts
  作者：Lidiane Meier、Misael Ferreira、Marcus M. Sá

  DOI：10.1002/hc.21001

  日期：——

  A convenient and general microwave-assisted method for the synthesis of stereochemically defined α-methylalkenoic acids and esters from allylic phosphonium salts in a basic aqueous medium is described. A selective preparation of acids or esters was dependent on the base (NaOH or NaHCO3) employed in the reaction and could be achieved with good to excellent yields under mild conditions in the absence

  描述了一种方便和通用的微波辅助方法，用于在碱性水介质中从烯丙基鏻盐合成立体化学定义的 α-甲基链烯酸和酯。酸或酯的选择性制备取决于反应中使用的碱（NaOH 或 NaHCO3），并且可以在不存在氢化物和还原剂的温和条件下以良好到极好的收率实现。© 2012 Wiley Periodicals, Inc. 杂原子化学 23:179–186, 2012; 在 wileyonlinelibrary.com 上在线查看这篇文章。DOI 10.1002/hc.21001
• AMINOPHOSPHINIC DERIVATIVES THAT CAN BE USED IN THE TREATMENT OF PAIN
  申请人：Roques Bernard

  公开号：US20110124601A1

  公开（公告）日：2011-05-26

  The present invention relates to a compound of the following general formula (I): R 1 —NH—CH(R 2 )—P(═O)(OR 3 )—CH 2 —C(R 4 )(R 5 )—CONH—CH(R 6 )—COOR 7 (I) or a pharmaceutically acceptable salt of the latter, an isomer or a mixture of isomers in any proportions, especially a mixture of enantiomers, and in particular a racemic mixture, for which R 1 represents a —C(═O)—O—C(R 8 )(R 9 )—OC(═O)—R 10 group; R 2 represents an optionally substituted hydrocarbon-based chain, an aryl or heteroaryl group or a methylene group substituted by a heterocycle; R 3 represents a hydrogen atom or a —C(R 12 )(R 13 )—OC(═O)—R 14 group; R 4 and R 5 form, together with the carbon that bears them, a saturated hydrocarbon-based ring or an optionally substituted piperidine ring or R 4 represents a hydrogen atom and R 5 represents a phenyl or a benzyl that is optionally substituted, a heteroaromatic ring or a methylene group substituted by a heterocycle; R 6 represents an optionally substituted hydrocarbon-based chain or a phenyl or a benzyl that is optionally substituted; and R 7 represents a hydrogen atom or a benzyl, alkyl, heteroaryl, alkylheteroaryl, —CHMe—COOR 18 , —CHR 19 —OC(═O)OR 20 and —CHR 19 —OC(═O)OR 20 group. The present invention also relates to the use of these compounds as a medicinal product, and in particular for the treatment of pain, more advantageously neuropathic and neuroinflammatory pain, to their method of synthesis and also to the compositions containing them.

  本发明涉及以下通式（I）的化合物：R1—NH—CH（R2）—P（═O）（OR3）—CH2—C（R4）（R5）—CONH—CH（R6）—COOR7或其药学上可接受的盐、异构体或任意比例的异构体混合物，特别是对映体混合物，尤其是外消旋混合物，其中R1代表—C（═O）—O—C（R8）（R9）—OC（═O）—R10基团；R2代表可选取代的碳氢链、芳基或杂环芳基基团或被杂环取代的亚甲基基团；R3代表氢原子或—C（R12）（R13）—OC（═O）—R14基团；R4和R5与承载它们的碳原子一起形成饱和碳氢基环或可选取代的哌啶环或R4代表氢原子，R5代表可选取代的苯基或苄基、杂环芳基环或被杂环取代的亚甲基基团；R6代表可选取代的碳氢链或可选取代的苯基或苄基；R7代表氢原子或苄基、烷基、杂环芳基、烷基杂环芳基、—CHMe—COOR18、—CHR19—OC（═O）OR20和—CHR19—OC（═O）OR20基团。本发明还涉及这些化合物作为药物的用途，特别是用于疼痛治疗，更有利的是神经病理性和神经炎性疼痛的治疗，以及它们的合成方法和含有它们的组合物。
• Asymmetric δ-Lactam Synthesis with a Monomeric Streptavidin Artificial Metalloenzyme
  作者：Isra S. Hassan、Angeline N. Ta、Michael W. Danneman、Natthawat Semakul、Matthew Burns、Corey H. Basch、Vanessa N. Dippon、Brian R. McNaughton、Tomislav Rovis

  DOI：10.1021/jacs.9b01596

  日期：2019.3.27

  Reliable design of artificial metalloenzymes (ArMs) to access transformations not observed in nature remains a long-standing and important challenge. We report that a monomeric streptavidin (mSav) Rh(III) ArM permits asymmetric synthesis of α,β-unsaturated-δ-lactams via a tandem C-H activation and [4+2] annulation reaction. These products are readily derivatized to enantioenriched piperidines, the most

  可靠地设计人工金属酶 (ArM) 以实现自然界中未观察到的转化，这仍然是一个长期存在的重要挑战。我们报告说，单体链霉亲和素 (mSav) Rh(III) ArM 允许通过串联 CH 活化和 [4+2] 环化反应不对称合成 α,β-不饱和-δ-内酰胺。这些产品很容易衍生为富含对映体的哌啶，这是 FDA 批准的药物中最常见的 N-杂环。在室温和水性条件下，以高达 99% 的产率和 97% 的对映体过量实现了所需的 δ-内酰胺。将 Rh 环戊二烯基 (Cp*) 催化剂嵌入 mSav 的活性位点可改善立体控制，并将反应性相对于分离的生物素化 Rh(III) 辅因子提高 7 倍。此外，
• Synthesis of tritium labelled thiorphan, an enkephalinase inhibitor
  作者：Shao-Yong Wu、Mohammad R. Masjedizadeh

  DOI：10.1002/jlcr.1566

  日期：2009.1

  Tritium labelling of the enkephalinase inhibitor, thiorphan, is complicated by the presence of mercapto functional group. Reactions often used in aromatic tritiation, such as halogination and catalytic halogen/tritium displacement, are adversely affected by the presence of the divalent sulfur moeity. By protecting the SH group with t-butyl group, the tritiation reaction proceeded smoothly without catalyst

  由于巯基官能团的存在，脑啡肽酶抑制剂噻吩的氚标记变得复杂。常用于芳族氚化的反应，如卤化和催化卤素/氚置换，受到二价硫部分存在的不利影响。通过用叔丁基保护 SH 基团，氚化反应顺利进行，没有催化剂中毒。使用 2-硝基苯亚磺酰氯和二硫苏糖醇 (DTT) 可以轻松高效地重新生成巯基官能团。如此获得的[ 3 H]-噻吩通过AN-HPLC具有>99%的放射化学纯度和18.42Ci/mmol的比活。[3H]-噻吩在 4°C 下储存在含有 10% 甲醇和 0.2% DTT 的水溶液中避光时表现出良好的稳定性。版权所有 © 2008 John Wiley & Sons, Ltd.
• [EN] PROCESS FOR SYNTHESIS OF TRITIATED AND DEUTERATED THIORPHAN AND ACETORPHAN<br/>[FR] PROCÉDÉ DE SYNTHÈSE DE THIORPHANE ET D'ACÉTORPHANE TRITIÉ OU DEUTÉRIÉ
  申请人：HOFFMANN LA ROCHE

  公开号：WO2009077386A1

  公开（公告）日：2009-06-25

  Methods for preparing tritium or deuterium labeled thiorphan comprising reacting a compound of formula (j), wherein m is from 1 to 5 and X is halo, with Z2 wherein Z is tritium or deuterium, in the presence of a catalyst, to form a compound of formula (k), wherein n is from 1 to 5, provided that n is less than or equal to m.

  制备氚或氘标记的硫酚的方法包括在催化剂存在下，将式(j)的化合物（其中m为1至5，X为卤素）与Z2（其中Z为氚或氘）反应，形成式(k)的化合物（其中n为1至5，且n小于等于m）。