(R)-N-(1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ethyl)acetamide | 1260955-13-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (R)-N-(1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ethyl)acetamide
• 英文别名: N-[(1R)-1-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]ethyl]acetamide
• CAS: 1260955-13-2
• 化学式: C₁₆H₂₄BNO₃
• 分子量: 289.182
• InChiKey: RYNZRWKSPLRIGP-LLVKDONJSA-N

物化性质

• 沸点：
  453.6±38.0 °C(Predicted)
• 密度：
  1.05±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.18
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  47.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R)-N-(1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ethyl)acetamide 在 N-溴代丁二酰亚胺(NBS) 、 copper(I) bromide 作用下， 以 乙腈 为溶剂， 反应 12.0h， 以87%的产率得到(R)-n-乙酰基-1-(4-溴苯基)乙胺
  参考文献：
  名称：

  Chemoenzymatic synthesis of boron-containing chiral amines and amides

  摘要：

  The first application of lipases as catalysts to obtain optically active boron-containing amines and amides is described. We studied several reaction conditions to achieve the kinetic resolution of boron-containing amines via enantioselective acylation mediated by Candida antarctica lipase B (CAL-B). Excellent enantioselectivity (E>200) and high enantiomeric excess (up to >99%) of both the remaining amines and amides were obtained. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.09.011
• 作为产物：
  描述：

  4-乙酰苯基硼酸,醇酯 在 吡啶 、 Candida boidinii formate dehydrogenase 、 L-丙氨酸 、 alanine dehydrogenase 、 磷酸吡哆醛 、 Chromobacterium violaceum ω-transaminase 、 甲酸铵 、 烟酰胺腺嘌呤双核苷酸磷酸盐 作用下， 以 aq. phosphate buffer 、 二甲基亚砜 、 乙酸乙酯 为溶剂， 反应 36.0h， 生成 (R)-N-(1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ethyl)acetamide
  参考文献：
  名称：

  Asymmetric reductive amination of boron-containing aryl-ketones using ω-transaminases

  摘要：

  The asymmetric reductive amination of aryl-ketones bearing various boron-functionalities (acid, ester or potassium trifluoroborates) was investigated employing enantiocomplementary omega-transaminases as catalysts. Under the optimized conditions, high conversions (up to 94%) and excellent ee's (up to >99%) were obtained providing access to both (R)- and (S)-configured amino-aryl boronates under mild reaction conditions. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2013.10.004

文献信息

• [EN] PYRAZOLE DERIVATIVES USEFUL AS INHIBITORS OF FAAH<br/>[FR] DÉRIVÉS DE PYRAZOLE UTILES COMME INHIBITEURS DE FAAH
  申请人：MERCK & CO INC

  公开号：WO2009151991A1

  公开（公告）日：2009-12-17

  The present invention is directed to certain imidazole derivatives which are useful as inhibitors of Fatty Acid Amide Hydrolase (FAAH). The invention is also concerned with pharmaceutical formulations comprising these compounds as active ingredients and the use of the compounds and their formulations in the treatment of certain disorders, including osteoarthritis, rheumatoid arthritis, diabetic neuropathy, postherpetic neuralgia, skeletomuscular pain, and fibromyalgia, as well as acute pain, migraine, sleep disorder, Alzheimer disease, and Parkinson's disease

  本发明涉及某些咪唑衍生物，其可用作脂肪酰胺水解酶（FAAH）的抑制剂。该发明还涉及包含这些化合物作为活性成分的药物配方，以及这些化合物及其配方在治疗某些疾病中的使用，包括骨关节炎、类风湿性关节炎、糖尿病神经病变、带状疱疹后神经痛、骨骼肌肉疼痛和纤维肌痛，以及急性疼痛、偏头痛、睡眠障碍、阿尔茨海默病和帕金森病。