2,3,4,5-四氢苯并[b]氮杂卓-1-甲醛 | 65596-57-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯氮卓类
• 中文名称: 2,3,4,5-四氢苯并[b]氮杂卓-1-甲醛
• 英文名称: 1-formyl-2,3,4,5-tetrahydro-1H-1-benzazepine
• 英文别名: 2,3,4,5-Tetrahydrobenzo[b]azepine-1-carbaldehyde；2,3,4,5-tetrahydro-1-benzazepine-1-carbaldehyde
• CAS: 65596-57-8
• 化学式: C₁₁H₁₃NO
• 分子量: 175.23
• InChiKey: SFSPHAVRUJCKDS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  2,3,4,5-四氢苯并[b]氮杂卓-1-甲醛 在 tris(bis(trimethylsilyl)amido)lanthanum(III) 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以91 %的产率得到2,3,4,5-四氢-1H-苯并[b]氮杂卓
  参考文献：
  名称：

  La-催化的甲酰胺脱羰基反应及其应用

  摘要：

  在这里，我们报告了甲酰胺的首次催化脱羰和脱羰加氢胺化，而不使用由氧化还原中性稀土催化剂启用的添加剂。该协议显示了完整的N-芳基/烯基甲酰胺选择性，从而提供了N-甲酰化和N-脱甲酰化方法的广泛创造性用途，并为最大限度地减少浪费和控制胺转化事件中所需的选择性开辟了新的前景。

  DOI：

  10.1021/acs.orglett.2c03981
• 作为产物：
  描述：

  2,3,4,5-四氢-1H-苯并[b]氮杂卓 、 二氧化碳 在 (三羟基)苯基硼酸钠 、 苯硅烷 作用下， 以 二乙二醇二甲醚 为溶剂， 100.0 ℃ 、250.0 kPa 条件下， 反应 12.0h， 以73%的产率得到2,3,4,5-四氢苯并[b]氮杂卓-1-甲醛
  参考文献：
  名称：

  四配位硼酸酯作为胺与二氧化碳还原甲酰化的催化剂

  摘要：

  我们报告三羟基芳基硼酸钠作为第一个坚固的四配位有机硼催化剂，用于CO 2的还原功能化。这些催化剂很容易从硼酸与金属氢氧化物的缩合反应中合成，可以有效地活化主族元素氢键。与BX 3型硼烷，硼酸和金属-BAr 4盐相比，在无过渡金属的条件下，三羟基芳基硼酸钠对各种胺（包括带有官能团的胺）表现出较高的还原性N-甲酰化反应性（106例）例如酯，烯烃，羟基，氰基，硝基，卤素，MeS–，醚基等。催化具有挑战性的吡啶胺的甲酰化反应的性能过高，为使用传统的甲酰化试剂提供了一种有前途的替代方法。机理研究支持将静电相互作用作为Si / B–H活化的关键，从而使碱金属硼酸盐成为用于CO 2加氢硼化，加氢硅烷化和还原甲酰化/甲基化的通用催化剂。

  DOI：

  10.1039/d0gc01741h

文献信息

• NOVEL PYRAZOLE DERIVATIVE
  申请人：MOCHIDA PHARMACEUTICAL CO., LTD.

  公开号：US20140378447A1

  公开（公告）日：2014-12-25

  It has been desired to develop a pharmaceutical composition, which is used in agents for preventing and/or treating various diseases related to PDE10 (e.g. mental disorder and neurodegenerative disorder). The present invention provides: compounds having PDE10 inhibitory effect, in particular, compounds having a 4-heteroarylpyrazole-5-carboxylic acid amide structure represented by the following formula (I), or their pharmaceutically acceptable salts, or their solvates; pharmaceutical compositions comprising, as active ingredients, the compounds, or their pharmaceutically acceptable salts, or their solvates; and medical use of the compounds, or their pharmaceutically acceptable salts, or their solvates.

  已经有人希望开发一种药物组合物，用于预防和/或治疗与PDE10相关的各种疾病（例如精神障碍和神经退行性疾病）。本发明提供：具有PDE10抑制作用的化合物，特别是具有以下式（I）所代表的4-杂环芳基吡唑-5-羧酰胺结构的化合物，或其药学上可接受的盐，或其溶剂化物；包含作为活性成分的化合物，或其药学上可接受的盐，或其溶剂化物的药物组合物；以及化合物的医学用途，或其药学上可接受的盐，或其溶剂化物。
• THIENO[2,3-b]PYRIDINE DERIVATIVE AND QUINOLINE DERIVATIVE, AND USE THEREOF
  申请人：The University of Tokyo

  公开号：US20190177336A1

  公开（公告）日：2019-06-13

  It is an object of the present invention to provide a compound inhibiting the binding between ALS-related mutant SOD1 and Derlin-1, a medicament comprising the compound, and a method for treating ALS by administering the medicament to a patient. More specifically, the aforementioned compound is represented by the following formula (1): wherein X represents a sulfur atom or —CH═CH—; A 1 to A 4 each independently represent a carbon atom or a nitrogen atom, and at least one of A 1 to A 4 is a nitrogen atom; R 1 represents a 1,2,3,4-tetrahydroquinolyl group (or a 3,4-dihydro-1(2H)-quinolyl group), a 3,4-dihydro-4,4-dimethyl-1(2H)-quinolyl group, a 2,3,4,5-tetrahydro-1H-1-benzazepinyl group, or a substituent represented by the following formula (2): wherein R 4 represents an unsubstituted or optionally substituted phenyl group, an unsubstituted or optionally substituted pyridyl group, or an unsubstituted or optionally substituted naphthyl group, and R 5 represents any one of a hydrogen atom, a lower alkyl group, a lower alkenyl group, a lower alkynyl group (optionally containing an oxygen atom and/or a double bond), or an unsubstituted or optionally substituted aromatic lower alkyl group; R 2 represents a hydrogen atom, a lower alkyl group, a lower acyl group, or an unsubstituted or optionally substituted aromatic lower alkyl group; and R 3 represents a hydrogen atom, or R 2 and R 3 may bind to each other to form a ring.

  本发明的目的是提供一种抑制ALS相关突变SOD1和Derlin-1结合的化合物，包括该化合物的药物以及通过向患者施用该药物治疗ALS的方法。具体而言，上述化合物由以下公式（1）表示：其中X表示硫原子或-CH═CH-；A1至A4分别独立表示碳原子或氮原子，且至少有一个为氮原子；R1表示1,2,3,4-四氢喹啉基（或3,4-二氢-1（2H）-喹啉基），3,4-二氢-4,4-二甲基-1（2H）-喹啉基，2,3,4,5-四氢-1H-1-苯并氮杂环基或由以下公式（2）表示的取代基：其中R4表示未取代或可选取代的苯基，未取代或可选取代的吡啶基或未取代或可选取代的萘基，而R5表示氢原子，低碳基，低烯基，低炔基（可选含氧原子和/或双键）或未取代或可选取代的芳香基低碳基中的任意一种；R2表示氢原子，低碳基，低酰基或未取代或可选取代的芳香基低碳基；而R3表示氢原子，或R2和R3可结合形成环。
• Thieno[2,3-b]pyridine derivative, quinoline derivative, and use thereof
  申请人：The University of Tokyo

  公开号：US10689394B2

  公开（公告）日：2020-06-23

  A compound represented by the following formula (1) is provided: wherein X represents a sulfur atom or —CH═CH—; A1 to A4 each independently represent a carbon atom or a nitrogen atom, and at least one of A1 to A4 is a nitrogen atom; R1 represents any one of a 1,2,3,4-tetrahydroquinolyl group (or a 3,4-dihydro-1(2H)-quinolyl group), a 3,4-dihydro-4,4-dimethyl-1(2H)-quinolyl group, a 2,3,4,5-tetrahydro-1H-1-benzazepinyl group, or a substituent represented by the following formula (2): wherein R4 represents a 2,3,4-trifluorophenyl group, a 4-iodophenyl group, a 2,3-difluorophenyl group, a 3,5-difluorophenyl group, a 5-fluoro-2-methylphenyl group, a 3-pentafluorosulfanylphenyl group, a 2,6-dimethylphenyl group, a 4-benzyloxyphenyl group, a 3,5-bis(trifluoromethyl)biphenyl group, a 4-tert-butylphenyl group, a 3-methoxyphenyl group, an unsubstituted or substituted pyridyl group, or an unsubstituted or substituted naphthyl group; R5 represents a hydrogen atom, a lower alkyl group, a lower alkenyl group, a lower alkynyl group optionally containing an oxygen atom and/or a double bond, or an unsubstituted or substituted aromatic lower alkyl group; R2 represents a hydrogen atom, a lower alkyl group, a lower acyl group, or an unsubstituted or substituted aromatic lower alkyl group; and R3 represents a hydrogen atom, or R2 and R3 may bind to each other to form a ring.

  提供了下式（1）所代表的化合物： 其中X代表硫原子或-CH═CH-；A1至A4各自独立地代表碳原子或氮原子，且A1至A4中至少有一个是氮原子；R1 代表 1，2，3，4-四氢喹啉基（或 3，4-二氢-1(2H)-喹啉基）、3，4-二氢-4，4-二甲基-1(2H)-喹啉基、2，3，4，5-四氢-1H-1-苯并氮杂卓基或下式(2)所代表的取代基中的任一个： 其中 R4 代表 2,3,4-三氟苯基基团、4-碘苯基基团、2,3-二氟苯基基团、3,5-二氟苯基基团、5-氟-2-甲基苯基基团、3-五氟硫代苯基基团、2,6-二甲基苯基基团4-苄氧基苯基、3,5-双（三氟甲基）联苯基、4-叔丁基苯基、3-甲氧基苯基、未取代或取代的吡啶基或未取代或取代的萘基；R5 代表氢原子、低级烷基、低级烯基、任选含有氧原子和/或双键的低级炔基、或未取代或取代的芳香族低级烷基； R2 代表氢原子、低级烷基、低级酰基、或未取代或取代的芳香族低级烷基；以及 R3 代表氢原子，或 R2 和 R3 可相互结合形成一个环。
• Dynamic and Static Conformational Analysis of Acylated Tetrahydrobenzazepines
  作者：Alfred Hassner、Boaz Amit、Vered Marks、Hugo E. Gottlieb

  DOI：10.1021/jo0340105

  日期：2003.9.1

  A detailed high-field NMR analysis of several acylated tetrahydrobenzazepines, supported by molecular mechanics calculations, indicates that the heterocyclic ring in these compounds exists in a chair conformation, with the carbonyl oriented anti to the aryl moiety in the dominant rotamer. Surprisingly, ring methylenes are typically diastereotopic at room temperature, as the barriers for the process of enantiomerization of the seven-membered ring are much higher than expected. It is shown that ring inversion is correlated (but not concerted) with rotation of the amide moiety, as the carbonyl is forced out of conjugation with the nitrogen in the transition state.
• In Situ‐Generated Cu ^I Catalytic System for Oxidative <i>N</i> ‐Formylation of N‐Heterocycles and Acyclic Amines with Methanol
  作者：Yujing Zhang、Xingchao Dai、Jixue Wang、Junxi Liang、Jabor Rabeah、Xia Tian、Xiaoqiang Yao、Yanbin Wang、Shaofeng Pang

  DOI：10.1002/cssc.202202104

  日期：2023.2.8

  AbstractThe development of a sustainable and simple catalytic system for N‐formylation of N‐heterocycles with methanol by direct coupling remains a challenge, owing to many competing side reactions, given the sensitivity of N‐heterocycles to many catalytic oxidation or dehydrogenation systems. This work concerns the development of an in situ‐generated CuI catalytic system for oxidative N‐formylation of N‐heterocycles with methanol that is based on the case study of a more typical 1,2,3,4‐tetrahydroquinoline as substrate. Aside from N‐heterocycles, some acyclic amines are also transformed into the corresponding N‐formamides in moderate yields. Furthermore, a probable reaction mechanism and reaction pathway are proposed and extension of work based on some findings leads to a demonstration that the formed ⋅O2− and ⋅OOH radicals in the catalytic system is related to the formation of undesired tar‐like products.