2-溴-5-甲基苯乙酸 | 203314-29-8

• 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: 2-溴-5-甲基苯乙酸
• 英文名称: 2-bromo-5-methylphenylacetic acid
• 英文别名: (2-bromo-5-methyl-phenyl)-acetic acid；(2-Brom-5-methyl-phenyl)-essigsaeure；2-(2-Bromo-5-methylphenyl)acetic acid
• CAS: 203314-29-8
• 化学式: C₉H₉BrO₂
• 分子量: 229.073
• InChiKey: ZSUNJHLJHAIXLZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 危险性防范说明：
  P261,P280,P301+P312,P302+P352,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

反应信息

• 作为反应物：
  描述：

  2-溴-5-甲基苯乙酸 在 sodium tetrahydroborate 、 四(三苯基膦)钯 、 三苯基膦 、 copper(l) chloride 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 、 乙腈 为溶剂， 反应 25.42h， 生成 2-(2-(2-bromoethyl)-4-methylphenyl)-1-((4-nitrophenyl)sulfonyl)aziridine
  参考文献：
  名称：

  通过In（OTf）3催化的串联环状取代控制形成六氢苯并[ e ]异吲哚和3-苯并pine庚因

  摘要：

  已经开发出戏剧性的N-取代基控制的2-（2-（2-溴乙基）苯基）-1-磺酰基氮丙啶与1，3-二羰基化合物的串联环化。当N-取代基是4-甲基苯磺酰基（Ts）时，氮丙啶的连续开环，亲核取代和内酰胺化发生，从而以高收率和良好的非对映选择性提供了一系列六氢苯并[ e ]异吲哚化合物。相反，当N-取代基为4-硝基苯磺酰基（Ns）时，通过氮丙啶的开环和亲核取代以高收率获得3-苯并ze庚因化合物。

  DOI：

  10.1021/acs.orglett.8b02406
• 作为产物：
  描述：

  3-甲基苯乙酸 在 溴 、 potassium carbonate 作用下， 以 水 、 异丙醇 为溶剂， 反应 6.0h， 生成 2-溴-5-甲基苯乙酸
  参考文献：
  名称：

  Optimization and Scale-up of a Pd-Catalyzed Aromatic C−N Bond Formation: A Key Step in the Synthesis of a Novel 5-HT_1B Receptor Antagonist

  摘要：

  Searching for the best synthetic route for a given target molecule is a complex task and, by the same token, a key deliverable from a process R&D department. In this vein the challenge for our group was to identify a sustainable manufacturing process for a chiral compound, AR-A2, to be developed for the treatment of certain neurological disorders. Besides designing a method for assembling the core (R)-2-aminotetralin nucleus, a key feature in the overall synthesis was to provide a robust procedure for creating a new C-N bond between an aromatic ring and a heterocyche moiety. The methodology employed a Buchwald-Hartwig coupling, and a highly efficient catalytic process was developed using Pd(OAc)(2) as precatalyst, with loadings as low as 0.47 mol % (in laboratory trials one order of magnitude lower) together with (R)BINAP as ligand. Optimizing the reaction conditions allowed a virtually quantitative conversion of the brominated aromatic substrate after heating to 110-115 degrees C in toluene for 4 h. Telescoping this step with a succeeding catalytic hydrogenation to effect an N-debenzylation, followed by precipitation of the benzoate salt offered an overall yield for the two consecutive steps of 88% at 125-kg batch size, combined with excellent stereochemical product purity of 98% ee.

  DOI：

  10.1021/op8000146

文献信息

• Chiral Magnesium Bisphosphate-Catalyzed Asymmetric Double C(sp³)–H Bond Functionalization Based on Sequential Hydride Shift/Cyclization Process
  作者：Keiji Mori、Ryo Isogai、Yuto Kamei、Masahiro Yamanaka、Takahiko Akiyama

  DOI：10.1021/jacs.8b02761

  日期：2018.5.23

  functionalization triggered by a sequential hydride shift/cyclization process. This reaction consists of stereoselective domino C(sp3)-H bond functionalization: (1) a highly enantio- and diastereoselective C(sp3)-H bond functionalization by chiral magnesium bisphosphate (first [1,5]-hydride shift), and (2) a highly diastereoselective C(sp3)-H bond functionalization by an achiral catalyst (Yb(OTf)3, second [1

  本文描述的是手性二磷酸镁催化的不对称双 C(sp3)-H 键官能化，由顺序氢化物移位/环化过程触发。该反应由立体选择性多米诺 C(sp3)-H 键官能化组成：(1) 手性二磷酸镁的高度对映选择性和非对映选择性 C(sp3)-H 键官能化（第一个 [1,5]-氢化物位移），和（ 2）通过非手性催化剂（Yb（OTf）3，第二个[1,5]-氢化物转移）进行高度非对映选择性的C（sp3）-H键官能化。
• 2- and 2,5-substituted phenylketoenols
  申请人：Bayer Aktiengesellschaft

  公开号：US06359151B2

  公开（公告）日：2002-03-19

  The invention relates to novel phenyl-substituted cyclic ketoenols of the formula (I) in which Het represents one of the groups  in which A, B, D, G, X and Z are each as defined in the description, to a plurality of processes and intermediates for their preparation, and to their use as pesticides.

  该发明涉及公式(I)中的新型苯基取代的环状酮烯醇，其中Het代表其中一种基团，在其中A、B、D、G、X和Z各自如描述中定义的多种过程和中间体的制备，以及它们作为杀虫剂的用途。
• [EN] USE OF DERIVATIVES OF 2, 4-DIHYDRO-[1,2,4]TRIAZOLE-3-THIONE AS INHIBITORS O FTEH ENZYME MYELOPEROXIDASE (MPO)<br/>[FR] UTILISATION DE DERIVES DE 2, 4-DIHYDRO-[1,2,4]TRIAZOLE-3-THIONES COMME INHIBITEURS DE L'ENZYME MYELOPEROXYDASE (MPO)
  申请人：ASTRAZENECA AB

  公开号：WO2004096781A1

  公开（公告）日：2004-11-11

  There is disclosed the use of a compound of formula (I) wherein X, Y, W and Q are as defined in the specification, and pharmaceutically acceptable salts thereof, in the manufacture of a medicament, for the treatment or prophylaxis of diseases or conditions in which inhibition of the enzyme myeloperoxidase (MPO) is beneficial. Certain novel compounds of formula (I) and pharmaceutically acceptable salts thereof are disclosed, together with processes for their preparation. The compounds of formulae (I) are MPO inhibitors and are thereby particularly useful in the treatment or prophylaxis of neuroinflammatory disorders.

  揭示了使用公式(I)中X、Y、W和Q如规范中定义的化合物及其药用盐，在制造药物中用于治疗或预防对髓过氧化物酶（MPO）抑制有益的疾病或症状。公开了某些公式(I)的新化合物及其药用盐，以及它们的制备方法。公式(I)的化合物是MPO抑制剂，因此在治疗或预防神经炎症性疾病中特别有用。
• Use of derivatives of 2, 4-dihydro-[1,2,4] triazole-3-thione as inhibitors of the enzyme myeloperoxidase (mpo)
  申请人：Svensson Mats

  公开号：US20070093483A1

  公开（公告）日：2007-04-26

  There is disclosed the use of a compound of formula (I) wherein X, Y, W and Q are as defined in the specification, and pharmaceutically acceptable salts thereof, in the manufacture of a medicament, for the treatment or prophylaxis of diseases or conditions in which inhibition of the enzyme myeloperoxidase (MPO) is beneficial. Certain novel compounds of formula (I) and pharmaceutically acceptable salts thereof are disclosed, together with processes for their preparation. The compounds of formulae (I) are MPO inhibitors and are thereby particularly useful in the treatment or prophylaxis of neuroinflammatory disorders.

  本发明揭示了使用化合物(I)的使用，其中X、Y、W和Q如规范中所定义，以及其药学上可接受的盐，在制造药物方面，用于治疗或预防抑制髓过氧化物酶（MPO）酶有益的疾病或状况。揭示了某些新型化合物(I)及其药学上可接受的盐，以及其制备方法。化合物(I)的MPO抑制剂，因此特别适用于治疗或预防神经炎症性疾病。
• Synthesis of Polysubstituted Naphthalenes by a Hydride Shift Mediated C–H Bond Functionalization/Aromatization Sequence
  作者：Koutarou Amano、Tomoko Kawasaki-Takasuka、Keiji Mori

  DOI：10.1021/acs.orglett.3c04355

  日期：2024.3.8

  A synthetic strategy for forming multisubstituted naphthalenes based on hydride shift mediated C(sp3)–H bond functionalization was developed. This strategy consists of three successive transformations: (1) an intramolecular hydride shift mediated C(sp3)–H bond functionalization; (2) a decarboxylative fragmentation; and (3) an oxidation reaction. When benzylidene malonates having a 2-alkoxyethyl group

  开发了一种基于氢化物位移介导的 C(sp 3 )–H 键功能化形成多取代萘的合成策略。该策略由三个连续的转化组成：（1）分子内氢化物位移介导的C（sp 3 ）–H键功能化； (2)脱羧裂解； (3)氧化反应。当在邻位具有2-烷氧基乙基的亚苄基丙二酸酯用催化量的Al(OTf) 3处理时，氢化物转移/环化反应顺利进行，以良好的化学产率提供四氢化萘衍生物。通过将所得的四氢化萘暴露于改进的Krapcho脱羧反应条件（LiCl、DMSO和在O 2气氛下加热），很容易将其转化为萘。也实现了这两个反应的一锅操作。