N,N-dimethyl-1H-indol-4-amine | 75446-72-9

• 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: N,N-dimethyl-1H-indol-4-amine
• 英文别名: N,N-dimethylindol-4-amine；4-N,N-dimethylaminoindole
• CAS: 75446-72-9
• 化学式: C₁₀H₁₂N₂
• 分子量: 160.219
• InChiKey: FAEBUZRCBKFFTN-UHFFFAOYSA-N

物化性质

• 沸点：
  313.5±15.0 °C(Predicted)
• 密度：
  1.145±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  19
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N,N-dimethyl-1H-indol-4-amine 在 sodium nitrate 、 dimethyl sulfide borane 、 溶剂黄146 、 三氟乙酸 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 生成 1-acetyl-4-(dimethylamino)-5-nitroindoline
  参考文献：
  名称：

  Effects of Aromatic Substituents on the Photocleavage of 1-Acyl-7-nitroindolines

  摘要：

  Photolysis of 1-acyl-7-nitroindolines in aqueous solution gives a carboxylic acid and a 7-nitrosoindole, These compounds are useful as photolabile precursors of carboxylic acids, particularly neuroactive amino acids. The effect of electron-donating substituents at the 4-position has been explored for its effect on photolysis efficiency. 4-Methoxy substitution improved the photolysis efficiency >2-fold but the 4-dimethylamino analogue was essentially inert. A 5-alkyl substituent, that blocks unwanted nitration at this position, reduced the beneficial effect of the 4-methoxy group. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00745-6
• 作为产物：
  描述：

  2-(2-dimethylamino-6-nitrophenyl)acetaldehyde semicarbazone 在 palladium 10% on activated carbon 氢气 作用下， 以 乙醇 为溶剂， 反应 6.0h， 以86%的产率得到N,N-dimethyl-1H-indol-4-amine
  参考文献：
  名称：

  1-Acyl-7-nitroindoline derivatives, their preparation and their use as photocleavable precursors

  摘要：

  含有一个与结构式（I）所代表的效应子结构式相连的光释放化合物，其中R1为氢；C1-10烷基或取代烷基；O(CH2)n—Y；N(COZ)(CH2)mY；或N[(CH2)mY′[(CH2)NY]; R2和R3分别选择自：氢；C1-10烷基或取代烷基；或R2和R3一起为环烷基；R4为氢；C1-10烷基或取代烷基；苯基或取代苯基；(CH2)nY；或(CH2)mO(CH2)nY；其中m和n分别在1和10之间；Y和Y′分别选择自氢、CO2H或其盐或OPO32−，Z为氢或C1-10烷基或取代烷基；X为效应子或能够与效应子偶联或转化的基团，能够在照射下释放效应子，通常通过紫外光的闪烁照射。因此，这些光释放化合物可用于将生物活性效应子，如神经活性氨基酸或金属螯合剂，输送到需要其活性的部位。

  公开号：

  US06765014B1

文献信息

• 1-Acyl-7-nitroindoline derivatives, their preparation and their use as photocleavable precursors
  申请人：Medical Research Council

  公开号：US06765014B1

  公开（公告）日：2004-07-20

  Photoreleasable compounds comprising a caging moiety linked to an effector moiety represented by structural formula (I) wherein R1 is hydrogen; C1-10 alkyl or substituted alkyl; O(CH2)n—Y; N(COZ)(CH2)mY; or N[(CH2)mY′[(CH2)NY]; R2 and R3 are independently selected from: hydrogen; C1-10 alkyl or substituted alkyl; or R2 and R3 together are cycloalkyl; R4 is hydrogen; C1-10 alkyl or substituted alkyl; phenyl or substituted phenyl; (CH2)nY; or (CH2)mO(CH2)nY; wherein m and n are independently between 1 and 10; Y and Y′ are independently selected from hydrogen, CO2H or salts thereof or OPO32−, Z is hydrogen or C1-10 alkyl or substituted alkyl; and, X is an effector moiety or a group capable of being coupled or converted to an effector moiety, which are capable of releasing the effector moiety on irradiation, typically by flash irradiation with UV light. The photoreleasable compounds can therefor be used to deliver biologically active effector moieties such as neuroactive amino acids or metal chelators to sites where their activity is required.

  含有一个与结构式（I）所代表的效应子结构式相连的光释放化合物，其中R1为氢；C1-10烷基或取代烷基；O(CH2)n—Y；N(COZ)(CH2)mY；或N[(CH2)mY′[(CH2)NY]; R2和R3分别选择自：氢；C1-10烷基或取代烷基；或R2和R3一起为环烷基；R4为氢；C1-10烷基或取代烷基；苯基或取代苯基；(CH2)nY；或(CH2)mO(CH2)nY；其中m和n分别在1和10之间；Y和Y′分别选择自氢、CO2H或其盐或OPO32−，Z为氢或C1-10烷基或取代烷基；X为效应子或能够与效应子偶联或转化的基团，能够在照射下释放效应子，通常通过紫外光的闪烁照射。因此，这些光释放化合物可用于将生物活性效应子，如神经活性氨基酸或金属螯合剂，输送到需要其活性的部位。
• Modulators of ATP-binding cassette transporters
  申请人：Vertex Pharmaceuticals Incorporated

  公开号：US10975061B2

  公开（公告）日：2021-04-13

  Compounds of the present invention and pharmaceutically acceptable compositions thereof, are useful as modulators of ATP-Binding Cassette (“ABC”) transporters or fragments thereof, including Cystic Fibrosis Transmembrane Conductance Regulator (“CFTR”). The present invention also relates to methods of treating ABC transporter mediated diseases using compounds of the present invention.

  本发明的化合物及其药学上可接受的组合物可用作 ATP 结合盒（"ABC"）转运体或其片段（包括囊性纤维化跨膜传导调节器（"CFTR"））的调节剂。本发明还涉及使用本发明化合物治疗 ABC 转运体介导的疾病的方法。
• Process for production of heteroaryl-type boron compounds with iridium catalyst
  申请人：Miyaura Norio

  公开号：US20050148775A1

  公开（公告）日：2005-07-07

  The present invention provides an economically and industrially superior simple process that enables the selective production of an aromatic heterocyclic monoboron compound and aromatic heterocyclic diboron compound at a satisfactory yield and in a desired ratio by reacting an aromatic heterocyclic compound and a boron compound in a single step under mild conditions while changing only the charged ratios of the raw materials. The present invention provides a production process of a heteroaryl mono- or diboron compound comprising an aromatic heterocyclic compound and a boron compound in the form of bis(pinacolate)diboron or pinacolate diborane in the presence of a iridium-containing catalyst and a ligand such as a bipyridyl ligand.

  本发明提供了一种经济上和工业上优越的简单工艺，通过在温和条件下使芳香杂环化合物和硼化合物进行单步反应，同时仅改变原料的带电比例，就能以满意的产率和所需的比例选择性地生产芳香杂环单硼化合物和芳香杂环二硼化合物。本发明提供了一种杂芳基单硼或二硼化合物的生产工艺，该工艺由芳香杂环化合物和双(频哪醇)二硼或频哪醇二硼烷形式的硼化合物在含铱催化剂和配体如双吡啶配体的存在下组成。
• A process for the rapid removal of dialkylamino-substituents from aromatic rings. Application to the expedient synthesis of (R)-tolterodine
  作者：Nick A. Paras、Bryon Simmons、David W.C. MacMillan

  DOI：10.1016/j.tet.2008.12.054

  日期：2009.4

  A range of N,N-dialkylanilines have been Successfully converted to the parent Substituted benzenes by a novel two-step pathway. The products are obtained in good yields and optical purity of adjacent stereocenters is maintained. This technology has been applied toward the synthesis of (R)-tolterodine. (C) 2009 Elsevier Ltd. All rights reserved.
• PROCESS FOR PRODUCTION OF HETEROARYL-TYPE BORON COMPOUNDS WITH IRIDIUM CATALYST
  申请人：MITSUBISHI RAYON CO., LTD.

  公开号：EP1481978B1

  公开（公告）日：2011-09-14