(2R,4R)-1-(tert-butoxycarbonyl)-4-(tert-butyldimethylsilyloxy)-2-cyanomethylpyrrolidine | 150309-59-4

• 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: (2R,4R)-1-(tert-butoxycarbonyl)-4-(tert-butyldimethylsilyloxy)-2-cyanomethylpyrrolidine
• 英文别名: N-Boc-4R-O-TBS-2S-cyanomethyl pyrrolidine；(2R,4R)-N-tert-butoxycarbonyl-4-tert-butyldimethylsiloxy-2-cyanomethylpyrrolidine；tert-butyl (2R,4R)-4-{[tert-butyl(dimethyl)silyl]oxy}-2-(cyanomethyl)pyrrolidine-1-carboxylate；tert-butyl (2R,4R)-4-[tert-butyl(dimethyl)silyl]oxy-2-(cyanomethyl)pyrrolidine-1-carboxylate
• CAS: 150309-59-4
• 化学式: C₁₇H₃₂N₂O₃Si
• 分子量: 340.538
• InChiKey: CLOJKJFGPZSLBU-ZIAGYGMSSA-N

物化性质

• 沸点：
  401.2±30.0 °C(Predicted)
• 密度：
  1.01±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  62.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2R,4R)-1-(tert-butoxycarbonyl)-4-(tert-butyldimethylsilyloxy)-2-cyanomethylpyrrolidine 在 ruthenium(IV) oxide 、 sodium periodate 作用下， 以 水 、 乙酸乙酯 为溶剂， 反应 10.0h， 以75%的产率得到(3R,5R)-1-(tert-butoxycarbonyl)-3-(tert-butyldimethylsilyloxy)-5-cyanomethylpyrrolidin-2-one
  参考文献：
  名称：

  Synthesis of (3S,5R)-3,5-diaminoazepan-2-one as a conformationally restricted surrogate of the Dab-Gly dipeptide

  摘要：

  An efficient and stereospecific synthesis of chiral 3,5-diaminoazcpan-2-one as a novel conformationally restricted surrogate of 2.4-diaminobutanoyl (Dab)-Gly dipeptide has been achieved by ail intramolecular transamidation with a catalytic hydrogenation as the key steps, starting from commercially available trans-4-hydroxy-L-proline. This methodology represents a powerful tool for the synthesis of the Dab-Gly dipeptide surrogate as one type of Freidinger epsilon-lactam. epsilon 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.04.017
• 作为产物：
  描述：

  氰化钠 、 (2S,4R)-1-(tert-butoxycarbonyl)-4-<(tert-butyldimethylsilyl)oxy>-2-<<(methylsulfonyl)oxy>methyl>pyrrolidine 以 二甲基亚砜 为溶剂， 反应 20.0h， 以70%的产率得到(2R,4R)-1-(tert-butoxycarbonyl)-4-(tert-butyldimethylsilyloxy)-2-cyanomethylpyrrolidine
  参考文献：
  名称：

  WO2007/10390

  摘要：

  公开号：

文献信息

• Amino/guanidino-functionalized N-(pyrrolidin-2-ethyl)glycine-based pet-PNA: Design, synthesis and binding with DNA/RNA
  作者：Sachin S. Gokhale、Vaijayanti A. Kumar

  DOI：10.1039/c004005c

  日期：——

  glycine-based PNA (pet-PNA) backbone, with 4-amino or 4-guanidino-functionalized pyrrolidine ring, confers constrained conformational flexibility on aegPNA. The oligomers bind to the target DNA and RNA sequences with increased sequence specificity and antiparallel versus parallel orientation selectivity. The easy post-synthetic guanidination gives very good access to the positively charged PNA oligomers

  基于N-（吡咯烷-2-乙基）甘氨酸的PNA（pet-PNA）主链4-氨基 或者 4-胍基功能化 吡咯烷环赋予aegPNA受限的构象灵活性。寡聚物以增加的序列特异性和反平行对平行取向选择性结合到靶DNA和RNA序列。易于合成后的胍基化非常容易获得带正电荷的PNA低聚物。
• Indazole Derivatives
  申请人：Ishibashi Asako

  公开号：US20080269211A1

  公开（公告）日：2008-10-30

  This invention relates to compounds of the formula (I): or pharmaceutically acceptable salts thereof, wherein: R 1 , R 2 , R 3 , A and m are each as described herein and compositions containing such compounds and the use of such compounds in the treatment of a condition mediated by 5-HT 4 agonistic activity such as, but not limited to, gastroesophageal reflux disease, gastrointestinal disease, gastric motility disorder, non-ulcer dyspepsia, functional dyspepsia, irritable bowel syndrome (IBS), constipation, dyspepsia, esophagitis, gastroesophageral disease, nausea, central nervous system disease, Alzheimer's disease, cognitive disorder, emesis, migraine, neurological disease, pain, cardiovascular disorders, cardiac failure, heart arrhythmia, diabetes and apnea syndrome.

  本发明涉及式(I)的化合物或其药学上可接受的盐，其中：R1、R2、R3、A和m如本文所述，并且包含这种化合物的组合物以及使用这种化合物治疗由5-HT4激动活性介导的疾病，例如但不限于胃食管反流病、胃肠疾病、胃动力障碍、非溃疡性消化不良、功能性消化不良、肠易激综合征（IBS）、便秘、消化不良、食管炎、胃食管疾病、恶心、中枢神经系统疾病、阿尔茨海默病、认知障碍、呕吐、偏头痛、神经系统疾病、疼痛、心血管疾病、心力衰竭、心律失常、糖尿病和呼吸暂停综合征。
• Indazole derivatives
  申请人：Pfizer Inc.

  公开号：US07906532B2

  公开（公告）日：2011-03-15

  This invention relates to compounds of the formula (I): or pharmaceutically acceptable salts thereof, wherein: R1, R2, R3, A and m are each as described herein and compositions containing such compounds and the use of such compounds in the treatment of a condition mediated by 5-HT4 agonistic activity such as, but not limited to, gastroesophageal reflux disease, gastrointestinal disease, gastric motility disorder, non-ulcer dyspepsia, functional dyspepsia, irritable bowel syndrome (IBS), constipation, dyspepsia, esophagitis, gastroesophageral disease, nausea, central nervous system disease, Alzheimer's disease, cognitive disorder, emesis, migraine, neurological disease, pain, cardiovascular disorders, cardiac failure, heart arrhythmia, diabetes and apnea syndrome.

  本发明涉及式(I)的化合物或其药学上可接受的盐，其中：R1、R2、R3、A和m如本文所述，并且包含这种化合物的组合物以及使用这种化合物治疗由5-HT4激动活性介导的病症，例如但不限于胃食管反流病、胃肠疾病、胃动力障碍、非溃疡性消化不良、功能性消化不良、肠易激综合征（IBS）、便秘、消化不良、食管炎、胃食管疾病、恶心、中枢神经系统疾病、阿尔茨海默病、认知障碍、呕吐、偏头痛、神经系统疾病、疼痛、心血管疾病、心力衰竭、心律失常、糖尿病和呼吸暂停综合征。
• WO2007/10390
  申请人：——

  公开号：——

  公开（公告）日：——
• Synthesis of (3S,5R)-3,5-diaminoazepan-2-one as a conformationally restricted surrogate of the Dab-Gly dipeptide
  作者：Ken-ichi Tanaka、Harumitsu Nemoto、Hiroyuki Sawanishi

  DOI：10.1016/j.tetasy.2005.04.017

  日期：2005.6

  An efficient and stereospecific synthesis of chiral 3,5-diaminoazcpan-2-one as a novel conformationally restricted surrogate of 2.4-diaminobutanoyl (Dab)-Gly dipeptide has been achieved by ail intramolecular transamidation with a catalytic hydrogenation as the key steps, starting from commercially available trans-4-hydroxy-L-proline. This methodology represents a powerful tool for the synthesis of the Dab-Gly dipeptide surrogate as one type of Freidinger epsilon-lactam. epsilon 2005 Elsevier Ltd. All rights reserved.