(S)-2-(aminomethyl)-N-cyclopropylmethylpyrrolidine | 66183-69-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: (S)-2-(aminomethyl)-N-cyclopropylmethylpyrrolidine
• 英文别名: [(2S)-1-(cyclopropylmethyl)pyrrolidinyl]methylamine；[(2S)-1-(cyclopropylmethyl)pyrrolidin-2-yl]methanamine
• CAS: 66183-69-5
• 化学式: C₉H₁₈N₂
• 分子量: 154.255
• InChiKey: QFIYFROFRTUSPW-VIFPVBQESA-N

物化性质

• 沸点：
  197.9±8.0 °C(Predicted)
• 密度：
  1.018±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  29.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-溴-2-羟基-3-甲氧基苯甲酸 、 (S)-2-(aminomethyl)-N-cyclopropylmethylpyrrolidine 在 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 三乙胺 作用下， 以 乙腈 为溶剂， 反应 24.0h， 以40%的产率得到(S)-5-溴-N-[(1-环丙基甲基-2-吡咯烷基)甲基]-2-羟基-3-甲氧基苯甲酰胺
  参考文献：
  名称：

  [11C]Cyclopropyl-FLB 457: A PET radioligand for low densities of dopamine D2 receptors

  摘要：

  (S)-5-Bromo- N-[(1-cyclopropylmethyl-2-pyrrolidinyl)methyl]-2,3-dimethoxybenzamide (4) has pico-molarin vitro binding affinity to D-2 receptor (K-i (D-2) = 0.003 nM) with lower affinity to D-3 receptor (K-i (D-3) = 0.22 nM). In this study, we describe radiosynthesis of [C-11]4 and evaluation of its binding characteristics in post-mortem human brain autoradiography and with PET in cynomolgus monkeys. The 11C labelled 4 was synthesized by using [C-11] methyltriflate in a methylation reaction with its phenolic precursor with good incorporation yield (64 +/- 11%, DCY) and high specific radioactivity > 370 GBq/mu mol (> 10 000 Ci/mmol). In post-mortem human brain autoradiography [C-11]4 exhibited high specific binding in brain regions enriched with dopamine D-2/D-3 receptors and low level of non-specific binding. In cynomolgus monkeys [C-11]4 exhibited high brain uptake reaching 4.4% ID at 7.5 min. The binding in the extrastriatal low density D-2-receptor regions; thalamus and frontal, parietal, temporal, and occipital cortex, was clearly visible. Pre-treatment with raclopride (1 mg/kg as tartrate) caused high reduction of binding in extrastriatal regions, including cerebellum. [C-11]4 is a promising radioligand for imaging D2 receptors in low density regions in brain. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.05.039
• 作为产物：
  描述：

  L-脯氨酰胺 在 lithium aluminium tetrahydride 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 48.0h， 生成 (S)-2-(aminomethyl)-N-cyclopropylmethylpyrrolidine
  参考文献：
  名称：

  Yang, Zhi-Ying; Mukherjee, Jogeshwar, Medicinal Chemistry Research, 1999, vol. 9, # 1, p. 1 - 8

  摘要：

  DOI：

文献信息

• Efficient stereoconservative synthesis of 1-substituted (S)- and
  申请人：Astra Lakemedel Aktiebolag

  公开号：US05300660A1

  公开（公告）日：1994-04-05

  Stereoconservative method for preparation of an (R)- or (S)-isomer of the compound of the formula I with at least 95% optical purity ##STR1## wherein R.sup.1 is a hydrogen atom, a saturated or unsaturated lower alkyl group, a cycloalkyl group, or a group (CH.sub.2).sub.m Ph wherein m is 0-3 and Ph is a substituted or unsubstituted phenyl group including 1) O,N-dialkylation, directly or stepwise of (R)- or (S)-proline 2) aminolysis 3) reduction to formation of the (R)- or (S)-isomer of the compound of the formula I, and new intermediates II and III in optical active form obtained by the reaction steps above and wherein R.sup.2 is defined as R.sup.1 above. ##STR2##

  用立体保守方法制备化合物的(R)-或(S)-异构体，其光学纯度至少为95%，其中R.sup.1是氢原子、饱和或不饱和的较低烷基基团、环烷基基团，或基团(CH.sub.2).sub.m Ph，其中m为0-3，Ph是取代或未取代的苯基团，包括1）(R)-或(S)-脯氨酸的直接或分步O，N-二烷基化，2）氨解作用，3）还原生成化合物的(R)-或(S)-异构体的方法，以及通过上述反应步骤获得的具有光学活性形式的新中间体II和III，其中R.sup.2被定义为上述的R.sup.1。
• Antithrombotic agents
  申请人：PFIZER INC.

  公开号：EP0997474B1

  公开（公告）日：2003-10-29
• US6180627
  申请人：——

  公开号：——

  公开（公告）日：——
• Hoegberg, Thomas; Raemsby, Sten; Stroem, Peter, Acta Chemica Scandinavica, 1989, vol. 43, # 7, p. 660 - 664
  作者：Hoegberg, Thomas、Raemsby, Sten、Stroem, Peter

  DOI：——

  日期：——
• US06180627B2
  申请人：——

  公开号：——

  公开（公告）日：——