5-methoxy-2,3-dihydroindole-1-carboxylic acid tert-butyl ester | 143262-11-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 5-methoxy-2,3-dihydroindole-1-carboxylic acid tert-butyl ester
• 英文别名: 1-(tert-butoxycarbonyl)-5-methoxyindoline；5-methoxy-N-tert-butoxycarbonylindoline；tert-butyl 5-methoxy-2,3-dihydroindole-1-carboxylate
• CAS: 143262-11-7
• 化学式: C₁₄H₁₉NO₃
• mdl: MFCD13183558
• 分子量: 249.31
• InChiKey: JXRHJQZYRSELDB-UHFFFAOYSA-N

物化性质

• 沸点：
  363.9±41.0 °C(Predicted)
• 密度：
  1.129±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-methoxy-2,3-dihydroindole-1-carboxylic acid tert-butyl ester 在 四甲基乙二胺 、 仲丁基锂 、 三氟乙酸 作用下， 以 乙醚 、 二氯甲烷 、 环己烷 为溶剂， 反应 2.5h， 生成 1-(5-methoxy-2,3-dihydro-1H-indol-7-yl)-1-phenylmethanone
  参考文献：
  名称：

  Synthesis, Structure−Activity Relationships, and Pharmacological Profile of 9-Amino-4-oxo-1-phenyl-3,4,6,7-tetrahydro[1,4]diazepino[6,7,1-hi]indoles:  Discovery of Potent, Selective Phosphodiesterase Type 4 Inhibitors

  摘要：

  The synthesis, structure-activity relationships, and biological properties of a novel series of; potent and selective phosphodiesterase type 4 (PDE4) inhibitors are described. These new aminodiazepinoindoles displayed in vitro PDE4 activity with submicromolar IC50 values and PDE4 selectivity vs PDE1, -3, and -5. Specifically, one compound (CI-1044, 10e) provided efficient in vitro inhibition of TNF alpha release from hPBMC and; hWB with IC50:values of 0.34 and 0.84 muM, respectively. This compound was found to exhibit potent in vivo activity in antigen-induced eosinophil recruitment in Brown-Norway rats (ED50 = 3.2 mg/kg po) and in production of TNF alpha in Wistar fats (ED50 = 2.8; mg/kg po). No emetic side effects at therapeutic doses were observed in ferrets.

  DOI：

  10.1021/jm000315p
• 作为产物：
  描述：

  N-BOC-5-甲氧基吲哚 在 acethylacetonato(1,5-cyclooctadiene)rhodium(I) 、 三苯基膦 氢气 作用下， 以 异丙醇 为溶剂， 80.0 ℃ 、4.9 MPa 条件下， 反应 3.0h， 以99%的产率得到5-methoxy-2,3-dihydroindole-1-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  铑-膦配合物催化五元杂芳族化合物加氢

  摘要：

  由 Rh(acac)(cod) 和 2 当量的三苯基膦原位生成的铑配合物是各种五元杂芳族化合物加氢的有效催化剂。

  DOI：

  10.1246/cl.2000.428

文献信息

• Synthesis of Functionalized Indolines and Dihydrobenzofurans by Iron and Copper Catalyzed Aryl C–N and C–O Bond Formation
  作者：Martyn C. Henry、Hans Martin Senn、Andrew Sutherland

  DOI：10.1021/acs.joc.8b02888

  日期：2019.1.4

  triflimide-catalyzed iodination, followed by a copper(I)-catalyzed intramolecular N- or O-arylation step leading to indolines, dihydrobenzofurans, and six-membered analogues. The general applicability and functional group tolerance of this method were exemplified by the total synthesis of the neolignan natural product, (+)-obtusafuran. DFT calculations using Fukui functions were also performed, providing a molecular

  描述了一种简单有效的一锅两步分子内芳基C–N和C–O键形成过程，该过程可利用铁和铜催化制备各种苯并稠合的杂环骨架。对活化的芳基环进行高度区域选择性，三氟甲磺酸铁（III）催化的碘化，然后进行铜（I）催化的分子内N-或O-芳基化步骤，生成二氢吲哚，二氢苯并呋喃和六元类似物。该方法的一般适用性和官能团耐受性由新木脂素天然产物（+）-奥布他呋喃的全合成例示。还进行了使用Fukui函数的DFT计算，从而为高度区域选择性的芳烃碘化过程提供了分子轨道原理。
• Heterocyclyl-substituted ring-fused pyridines and pyrimidines as corticotropin releasing hormone(CRH) antagonists, useful for treating CNS and stress-related disorders
  申请人：DuPont Pharmaceuticals Company

  公开号：US06245769B1

  公开（公告）日：2001-06-12

  Corticotropin releasing factor (CRF) antagonists of Formula (I): and their use in treating psychiatric disorders and neurological diseases, anxiety-related disorders, post-traumatic stress disorder, supranuclear palsy and feeding disorders as well as treatment of immunological, cardiovascular or heart-related diseases and colonic hypersensitivity associated with psychopathological disturbance and stress in mammals.

  皮质释放因子（CRF）拮抗剂的化学式（I）：及其在治疗精神障碍和神经系统疾病、焦虑相关障碍、创伤后应激障碍、上核性麻痹和进食障碍以及治疗与哺乳动物中的心理病理紊乱和应激相关的结肠过敏性所关联的免疫、心血管或心脏疾病方面的用途。
• Antibacterial methods and compositions
  申请人：——

  公开号：US20040224981A1

  公开（公告）日：2004-11-11

  Disclosed is a pharmaceutical composition comprising an aminoacyl tRNA synthetase inhibitor and another antibacterial agent, including another aminoacyl tRNA synthetase inhibitor.

  本发明揭示了一种药物组合物，包括一种氨酰tRNA合成酶抑制剂和另一种抗菌剂，其中包括另一种氨酰tRNA合成酶抑制剂。
• Heterocyclyl-substituted ring-fused pyridines and pyrimidines as corticotropin releasing hormone (CRH) antagonists, useful for treating cns and stress-related disorders
  申请人：——

  公开号：US20010025042A1

  公开（公告）日：2001-09-27

  Corticotropin releasing factor (CRF) antagonists of Formula (I): 1 and their use in treating psychiatric disorders and neurological diseases, anxiety-related disorders, post-traumatic stress disorder, supranuclear palsy and feeding disorders as well as treatment of immunological, cardiovascular or heart-related diseases and colonic hypersensitivity associated with psychopathological disturbance and stress in mammals.

  Corticotropin releasing factor (CRF)拮抗剂的公式（I）：1及其用于治疗精神障碍和神经系统疾病、焦虑相关障碍、创伤后应激障碍、上行性麻痹和进食障碍，以及治疗哺乳动物中与心理病理紊乱和压力相关的免疫、心血管或心脏相关疾病和结肠过敏性反应。
• 2-NH-heteroarylimidazoles with antibacterial activity
  申请人：Berge John

  公开号：US20060014748A1

  公开（公告）日：2006-01-19

  Compounds of formula (I): are inhibitors of bacterial methionyl tRNA synthetase and are of use in treating bacterial infections.

  公式（I）的化合物是细菌甲硫氨酸tRNA合成酶的抑制剂，可用于治疗细菌感染。