N-(3-bromopropyl)-3-hydroxy-1-isoindolinone | 124846-89-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: N-(3-bromopropyl)-3-hydroxy-1-isoindolinone
• 英文别名: 2-(3-bromopropyl)-3-hydroxy-1-isoindolinone；3-Hydroxy-2-(3-bromopropyl)-1-oxoisoindolin；2-(3-bromopropyl)-3-hydroxy-3H-isoindol-1-one
• CAS: 124846-89-5
• 化学式: C₁₁H₁₂BrNO₂
• 分子量: 270.126
• InChiKey: ZBFGUCHCLIHZCM-UHFFFAOYSA-N

物化性质

• 熔点：
  94 °C
• 沸点：
  421.6±45.0 °C(Predicted)
• 密度：
  1.585±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  40.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(3-bromopropyl)-3-hydroxy-1-isoindolinone 在 盐酸 作用下， 以 丙酮 为溶剂， 反应 3.5h， 生成
  参考文献：
  名称：

  Structure−Activity Relationships in a Series of Bisquaternary Bisphthalimidine Derivatives Modulating the Muscarinic M₂-Receptor Allosterically

  摘要：

  Hexane-bisammonium-type compounds containing lateral phthalimide moieties are well-established ligands of the common allosteric binding site of muscarinic M-2 receptors. Previous structure-activity relationships (SAR) revealed two positively charged centers and two lateral phthalimide moieties in a defined arrangement to be essential of a high allosteric potency. The purpose of this study was to replace one carbonyl group of the phthalimides with hydrogens, hydroxy, alkoxy, phenyl, benzyl, and benzylidene groups in order to check the influence of these substituents on the allosteric activity in antagonist-linked receptors. The analysis of the quantitative SAR indicated that a high allosteric potency is related to a certain amount of rigidity as well as polarizibility and the ability to form hydrophobic interactions.

  DOI：

  10.1021/jm991136e
• 作为产物：
  描述：

  N-(3-溴丙基)苯二胺 在 samarium diiodide 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以48%的产率得到N-(3-bromopropyl)-3-hydroxy-1-isoindolinone
  参考文献：
  名称：

  N-碘代烷基环状酰亚胺的还原环化成二碘化sa诱导的氮稠合多环酰​​胺

  摘要：

  已经研究了SmI 2促进的在酰亚胺氮上具有3-碘丙基或4-碘丁基的环状酰亚胺的环化，以构建氮稠合的多环酰胺。

  DOI：

  10.1016/0040-4039(96)00374-7

文献信息

• Reductive cyclization of N-iodoalkyl cyclic imides to nitrogen-fused polycyclic amides induced by samarium diiodide
  作者：Deok-Chan Ha、Chang-Soo Yun、Eunsun Yu

  DOI：10.1016/0040-4039(96)00374-7

  日期：1996.4

  SmI2-promoted cyclizations of cyclic imides having 3-iodopropyl or 4-iodobutyl groups on the imide nitrogen have been studied for construction of nitrogen-fused polycyclic amides.

  已经研究了SmI 2促进的在酰亚胺氮上具有3-碘丙基或4-碘丁基的环状酰亚胺的环化，以构建氮稠合的多环酰胺。
• Isoindolinone derivatives, processes for preparing them and medicines
  申请人：Rhone-Poulenc

  公开号：US04999355A1

  公开（公告）日：1991-03-12

  Compounds of formula: ##STR1## in which: either R.sub.1 represents 4-phenyl-1,2,3,6-tetrahydro-1-pyridyl or 4-(4-fluorophenyl)-1,2,3,6-tetrahydro-1-pyridyl, R.sub.2 represents hydrogen, alkoxy of 1 or 2 carbon atoms, hydroxyl, alkyl, alkylthio, alkylcarbonyloxy, phenylalkylcarbonyloxy, phenylalkyl or --NR.sub.4 R.sub.5 in which R.sub.4 represents hydrogen or alkyl and R.sub.5 represents alkyl, phenyl, monohalogenated phenyl or pyridyl, and R.sub.3 represents a hydrogen atom, or else R.sub.2 represent phenyl and R.sub.3 represents hydrogen or hydroxyl; or R.sub.1 represnets 4-phenyl-1-piperazinyl whose phenyl nucleus has a substituent halogen atom or hydroxyl radical in the 4-position, R.sub.2 represents alkoxy and R.sub.3 represents hydrogen; it being understood that when R.sub.1 represents the 4-phenyl-1,2,3,6-tetrahydro-1-pyridyl radical, R.sub.2 is not hydroxyl and that, unless otherwise stated, the alkyl and alkoxy radicals and the alkyl and alkoxy portions contain 1 to 4 carbon atoms each in a straight or branched chain, and addition salts thereof with an inorganic or organic acid, are useful in therapy for their serotonin antagonist properties.

  式（I）化合物： ##STR1## 其中：R1代表4-苯基-1,2,3,6-四氢-1-吡啶基或4-(4-氟苯基)-1,2,3,6-四氢-1-吡啶基，R2代表氢、1或2个碳原子的烷氧基、羟基、烷基、烷硫基、烷酰氧基、苯基烷酰氧基、苯基烷基或--NR4R5，其中R4代表氢或烷基，R5代表烷基、苯基、单卤代苯基或吡啶基，且R3代表氢原子；或者R2代表苯基，R3代表氢或羟基；或者R1代表4-苯基-1-哌嗪基，其苯环在4位上有一个取代的卤素原子或羟基，R2代表烷氧基，R3代表氢；须知当R1代表4-苯基-1,2,3,6-四氢-1-吡啶基时，R2不是羟基，且除非另有说明，烷基和烷氧基基团以及烷基和烷氧基部分各自含有1至4个碳原子，呈直链或支链，以及与无机或有机酸形成的加成盐，由于其血清素拮抗特性，在治疗中具有用途。
• Isoindoles having cardiovascular activity
  申请人：Italfarmaco S.p.A.

  公开号：US05376673A1

  公开（公告）日：1994-12-27

  Isoindole compounds of the formula (I) ##STR1## wherein R.sub.1 represents hydrogen; C.sub.1 -C.sub.6 alkyl; benzyl optionally substituted with halogen, hydroxy, C.sub.1 -C.sub.6 alkoxy, methylenedioxy; C.sub.2 -C.sub.8 aliphatic acyl; benzoyl optionally substituted with halogen, hydroxy, C.sub.1 -C.sub.6 alkoxy, C.sub.2 -C.sub.6 alkanoyl, C.sub.2 -C.sub.6 alkanoyloxy, C.sub.1 -C.sub.4 alkyl, trifluoromethyl, methylenedioxy; R.sub.2 -R.sub.3 are selected independently from hydrogen; halogen; C.sub.1 -C.sub.4 alkyl; trifluoromethyl; hydroxy; nitro; amino; mono or di C.sub.1 -C.sub.4 alkylamino; cyano; C.sub.1 -C.sub.6 alkoxy; C.sub.2 -C.sub.6 alkoxycarbonyl; Y is ethylene, or a straight or branched alkylene chain containing from 3 to 6 carbon atoms, and the salts thereof of pharmaceutically acceptable acids. The compounds possess antianginal activity and are used in the preparation of medicaments for antianginal therapy.

  式(I)的异吲哚化合物 ##STR1## 其中R.sub.1代表氢; C.sub.1-C.sub.6烷基; 可选用卤素，羟基，C.sub.1-C.sub.6烷氧基，亚甲二氧基取代的苯甲基; C.sub.2-C.sub.8脂肪酰基; 可选用卤素，羟基，C.sub.1-C.sub.6烷氧基，C.sub.2-C.sub.6烷酰基，C.sub.2-C.sub.6烷酰氧基，C.sub.1-C.sub.4烷基，三氟甲基，亚甲二氧基取代的苯甲酰基; R.sub.2-R.sub.3独立选择自氢; 卤素; C.sub.1-C.sub.4烷基; 三氟甲基; 羟基; 硝基; 氨基; 单或双C.sub.1-C.sub.4烷基氨基; 氰基; C.sub.1-C.sub.6烷氧基; C.sub.2-C.sub.6烷氧羰基; Y为乙烯或含有3至6个碳原子的直链或支链烷基链，以及其在药学上可接受的酸盐。这些化合物具有抗心绞痛活性，并用于制备抗心绞痛治疗药物。
• COMTE, MARIE-THERESE;GUEREMY, CLAUDE;PONSINET, GERARD
  作者：COMTE, MARIE-THERESE、GUEREMY, CLAUDE、PONSINET, GERARD

  DOI：——

  日期：——
• ISOINDOLES HAVING CARDIOVASCULAR ACTIVITY
  申请人：ITALFARMACO S.p.A.

  公开号：EP0576475B1

  公开（公告）日：1995-09-20