2-(3,5-二甲氧基苯基)吡咯烷 | 367281-01-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 中文名称: 2-(3,5-二甲氧基苯基)吡咯烷
• 英文名称: 2-(3,5-dimethoxyphenyl)pyrrolidine
• CAS: 367281-01-4
• 化学式: C₁₂H₁₇NO₂
• 分子量: 207.272
• InChiKey: SCIDTXFHJJWWTD-UHFFFAOYSA-N

物化性质

• 沸点：
  323℃
• 密度：
  1.052
• 闪点：
  130℃

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  30.5
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  2-(3,5-二甲氧基苯基)吡咯烷 在 PPA 作用下， 生成
  参考文献：
  名称：

  Pyrroloisoquinoline antidepressants. 3. A focus on serotonin

  摘要：

  A collection of hexahydropyrroloisoquinoline derivatives (1-22), which represent a class of compounds that inhibit the neuronal uptake of dopamine (DA), norepinephrine (NE), and serotonin (5-HT), was investigated in vivo for serotonin-potentiating properties in the mouse head-twitch and rat serotonin syndrome assays. The p-methylthio compound 3b (McN-5652-Z) was found to possess exceptional activity in these assays, and the activity was attributable almost exclusively to the (+)-6S,10bR enantiomer. Ten closely related analogues were synthesized, tested, and compared among themselves and with some previously prepared compounds, both in vivo and in vitro. Several trans diastereomers exhibited strong inhibition of 5-HT uptake and substantial potentiation of 5-HT, while the cis diastereomers (3a, 4a, and 10a) tested were virtually devoid of such activity. Although 3b was only moderately selective in inhibiting the uptake of 5-HT vs NE, its 10-substituted analogues 4b, 7b-9b had improved 5-HT selectivity relative to NE, to the extent of 20-25 times (150-200 times relative to DA). Of these more selective compounds (in vitro), only 4b and 7b had substantial activity in vivo. Sulfoxide 11b appeared to function as a prodrug of 3b in vivo.

  DOI：

  10.1021/jm00172a018
• 作为产物：
  描述：

  N-(3-chloropropyl)-(3,5-dimethoxyphenyl)methanimine 在 lithium 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以84%的产率得到2-(3,5-二甲氧基苯基)吡咯烷
  参考文献：
  名称：

  A New and Direct Synthesis of 2-Substituted Pyrrolidines

  摘要：

  DOI：

  10.1021/jo010419n

文献信息

• AROMATIC HETEROCYCLIC DERIVATIVE AND PHARMACEUTICAL
  申请人：Nippon Shinyaku Co., Ltd.

  公开号：EP2857398A1

  公开（公告）日：2015-04-08

  The main purpose of the invention is to provide a novel aromatic heterocyclic derivative or a pharmaceutically acceptable salt thereof. Examples of the invention include aromatic heterocyclic derivatives represented by general formula [1] and pharmaceutically acceptable salts thereof. In formula [1], R1 represents phenyl optionally substituted with one or two groups selected from the group consisting of halogens ,as well as alkyls and alkoxys optionally substituted by halogens; R2 represents a hydrogen, an alkyl, cycloalkyl, or alkoxy optionally substituted by a halogen, or a heteroaryl optionally substituted by an alkyl; X represents CR3, and Y represents N or CR4, or X represents N, and Y represents CR4; and Z represents CR5 or N.

  该发明的主要目的是提供一种新的芳香杂环衍生物或其药用可接受盐。该发明的示例包括由一般式[1]表示的芳香杂环衍生物和其药用可接受盐。在式[1]中，R1代表苯基，可以选择地取代一个或两个来自卤素、以及选择性地取代为卤素的烷基和烷氧基的基团之一；R2代表氢、烷基、环烷基或选择性地取代为卤素的烷氧基，或选择性地取代为烷基的杂芳基；X代表CR3，Y代表N或CR4，或X代表N，Y代表CR4；Z代表CR5或N。
• SUBSTITUTED PYRROLIDINES AS ROS TYROSINE KINASE INHIBITORS
  申请人：NIPPON SHINYAKU CO., LTD.

  公开号：US20170143722A1

  公开（公告）日：2017-05-25

  The main purpose of the invention is to provide a novel aromatic heterocyclic derivative or a pharmaceutically acceptable salt thereof. Examples of the invention include aromatic heterocyclic derivatives represented by general formula [1] and pharmaceutically acceptable salts thereof. In formula [1]: R 1 represents phenyl optionally substituted with one or two groups selected from the group consisting of halogens, as well as alkyls and alkoxys optionally substituted by halogens; R 2 represents hydrogen, an alkyl, cycloalkyl, or alkoxy optionally substituted by a halogen, or a heteroaryl optionally substituted by an alkyl; X represents CR 3 , and Y represents N or CR 4 , or X represents N, and Y represents CR 4 ; and Z represents CR 5 or N.
• US9580413B2
  申请人：——

  公开号：US9580413B2

  公开（公告）日：2017-02-28
• Pyrroloisoquinoline antidepressants. 3. A focus on serotonin
  作者：Bruce E. Maryanoff、Jeffry L. Vaught、Richard P. Shank、David F. McComsey、Michael J. Costanzo、Samuel O. Nortey

  DOI：10.1021/jm00172a018

  日期：1990.10

  A collection of hexahydropyrroloisoquinoline derivatives (1-22), which represent a class of compounds that inhibit the neuronal uptake of dopamine (DA), norepinephrine (NE), and serotonin (5-HT), was investigated in vivo for serotonin-potentiating properties in the mouse head-twitch and rat serotonin syndrome assays. The p-methylthio compound 3b (McN-5652-Z) was found to possess exceptional activity in these assays, and the activity was attributable almost exclusively to the (+)-6S,10bR enantiomer. Ten closely related analogues were synthesized, tested, and compared among themselves and with some previously prepared compounds, both in vivo and in vitro. Several trans diastereomers exhibited strong inhibition of 5-HT uptake and substantial potentiation of 5-HT, while the cis diastereomers (3a, 4a, and 10a) tested were virtually devoid of such activity. Although 3b was only moderately selective in inhibiting the uptake of 5-HT vs NE, its 10-substituted analogues 4b, 7b-9b had improved 5-HT selectivity relative to NE, to the extent of 20-25 times (150-200 times relative to DA). Of these more selective compounds (in vitro), only 4b and 7b had substantial activity in vivo. Sulfoxide 11b appeared to function as a prodrug of 3b in vivo.
• A New and Direct Synthesis of 2-Substituted Pyrrolidines
  作者：Miguel Yus、Tatiana Soler、Francisco Foubelo

  DOI：10.1021/jo010419n

  日期：2001.9.1