methyl 1-acetyl-4-methoxyindoline-7-acetate | 295325-83-6

• 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: methyl 1-acetyl-4-methoxyindoline-7-acetate
• 英文别名: methyl 2-(1-acetyl-4-methoxy-2,3-dihydroindol-7-yl)acetate
• CAS: 295325-83-6
• 化学式: C₁₄H₁₇NO₄
• 分子量: 263.293
• InChiKey: IUTMVGFVDLCYBS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 1-acetyl-4-methoxyindoline-7-acetate 在 sodium nitrate 、 三氟乙酸 作用下， 反应 4.0h， 以38%的产率得到methyl (1-acetyl-4-methoxy-5-nitroindolin-7-yl)acetate
  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
• 作为产物：
  描述：

  1-acetyl-4-methoxyindoline 在 三氯化铝 、 高氯酸 、 thallium(I) nitrate 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 7.0h， 生成 methyl 1-acetyl-4-methoxyindoline-7-acetate
  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

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：EP1161418A1

  公开（公告）日：2001-12-12
• US6765014B1
  申请人：——

  公开号：US6765014B1

  公开（公告）日：2004-07-20
• [EN] 1-ACYL-7-NITROINDOLINE DERIVATIVES, THEIR PREPARATION AND THEIR USE AS PHOTOCLEAVABLE PRECURSORS<br/>[FR] DERIVES DE 1-ACYL-7-NITROINDOLINE, LEUR PREPARATION ET LEUR UTILISATION COMME PRECURSEURS PHOTOLIBERABLES
  申请人：MEDICAL RES COUNCIL

  公开号：WO2000055133A1

  公开（公告）日：2000-09-21

  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 C¿1-10? 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 therefore be used to deliver biologically active effector moieties such as neuroactive amino acids or metal chelators to sites where their activity is required.