(1S,4R) 2-aza-bicyclo<2.2.1>heptane | 175275-72-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: (1S,4R) 2-aza-bicyclo<2.2.1>heptane
• 英文别名: (1S,4R)-2-aza-bicyclo[2.2.1]heptane；(1S,4R)-2-Azabicyclo[2.2.1]heptane
• CAS: 175275-72-6
• 化学式: C₆H₁₁N
• 分子量: 97.16
• InChiKey: GYLMCBOAXJVARF-RITPCOANSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  7
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (1S,4R) 2-aza-bicyclo<2.2.1>heptane 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 caesium carbonate 作用下， 以 1,4-二氧六环 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 N-(5-(2-(2-azabicyclo[2.2.1]heptan-2-yl)acetamido)-2-fluorophenyl)-6-(1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyrazine-3-carboxamide
  参考文献：
  名称：

  WO2023/247595

  摘要：

  公开号：
• 作为产物：
  描述：

  (+)-(1R,1'S)-2-(1'-Phenylethyl)-2-azabicyclo<2.2.1>hept-5-ene 在 palladium dihydroxide 、 palladium on activated charcoal 氢气 作用下， 以 溶剂黄146 、 乙酸乙酯 为溶剂， 反应 28.25h， 生成 (1S,4R) 2-aza-bicyclo<2.2.1>heptane
  参考文献：
  名称：

  手性 2-Aza-双环 [2.2.1] 庚烷合成的改进方法

  摘要：

  摘要 Grieco 的 2-氮杂-双环 [2.2.1] 庚烷合成方案经过修改，适用于大规模制备。该材料的光学纯度很容易通过手性盐纯化来提高。

  DOI：

  10.1080/00397919608003651

文献信息

• NOVEL SUBSTITUTED INDANES, METHOD FOR THE PRODUCTION THEREOF, AND USE THEREOF AS DRUGS
  申请人：Schwink Lothar

  公开号：US20120022039A1

  公开（公告）日：2012-01-26

  The invention relates to substituted indanes and derivatives thereof, to physiologically acceptable salts and physiologically functional derivatives thereof, to the production thereof, to drugs containing at least one substituted indane according to the invention or derivative thereof, and to the use of the substituted indanes according to the invention and to derivatives thereof as MCH antagonists.

  该发明涉及取代吲哚烷及其衍生物，以及其生理上可接受的盐和生理功能衍生物，以及其生产，包含至少一种根据该发明的取代吲哚烷或其衍生物的药物，以及将根据该发明的取代吲哚烷及其衍生物用作MCH拮抗剂。
• Data-Rich Experimentation Enables Palladium-Catalyzed Couplings of Piperidines and Five-Membered (Hetero)aromatic Electrophiles
  作者：Aaron C. Sather、Theodore A. Martinot

  DOI：10.1021/acs.oprd.9b00233

  日期：2019.8.16

  palladium-catalyzed C–N cross-coupling methodology, high-throughput experimentation was used to identify a catalyst capable of fusing piperidine-based nucleophiles with five-membered (hetero)aromatic bromides. A decomposition pathway for the standard electrophile was found, and a base screen was used to identify conditions that suppress this undesired transformation. Building on this, systematic optimization using

  为了规避钯催化的C–N交叉偶联方法中的电流限制，使用了高通量实验来鉴定能够将基于哌啶的亲核试剂与五元（杂）芳族溴化物融合的催化剂。发现了标准亲电试剂的分解途径，并且使用基础筛选来鉴定抑制该不希望有的转化的条件。在此基础上，使用“实验设计”方法进行系统优化可提供温和的反应条件，然后将其应用于各种偶联伙伴。
• Substituted benzothiazole amide derivatives
  申请人：——

  公开号：US20030149036A1

  公开（公告）日：2003-08-07

  A compound of formula I and a method of treatment of diseases, related to modulation of the adenosine A 2 receptor system comprising administering a compound of formula 1 to a person in need of such treatment.

  公式I的化合物和一种治疗疾病的方法，与调节腺苷A2受体系统有关，包括给需要此类治疗的人口服公式1的化合物。
• Orally available pyridinylpyrimidine derivatives as novel RANKL-induced osteoclastogenesis inhibitors
  作者：Junji Miyata、Chiyoshi Kasahara、Toru Asano、Shinji Ito、Norio Seki、Yasuko Kato、Noriyuki Morikawa、Kazuyoshi Nozaki、Kouji Nishimura、Hisashi Akamatsu、Yusuke Taguchi、Tomonori Yamaguchi、Yoshito Abe、Mitsuru Ohkubo、Toshihiro Watanabe、Mitsuaki Ohta、Makoto Takeuchi

  DOI：10.1016/j.bmcl.2012.06.087

  日期：2012.9

  An HTS campaign led to the identification of 4-pyrroldino-2-(pyridin-2-yl) pyrimidine compound 1 as an RANKL-induced osteoclastogenesis inhibitor. The compound 1 showed high clearance values in microsomes, however. Modification of the pyrrolidino group to a benzylamino group improved human microsomal stability with a slight loss of in vitro activity. Substitution at the ortho position of the benzyl group ameliorated in vitro activity, and further fluorination of the benzyl group improved microsomal stability in rodents. Representative members of this series, compounds 20 and 23, exhibited efficacy in RANKL-induced osteopenic mice when administered orally at 0.3 mg/kg. (C) 2012 Elsevier Ltd. All rights reserved.
• Orally bioavailable, indole-based nonpeptide GnRH receptor antagonists with high potency and functional activity
  作者：Wallace T. Ashton、Rosemary M. Sisco、Gerard R. Kieczykowski、Yi Tien Yang、Joel B. Yudkovitz、Jisong Cui、George R. Mount、Rena Ning Ren、Tsuei-Ju Wu、Xiaolan Shen、Kathryn A. Lyons、An-Hua Mao、Josephine R. Carlin、Bindhu V. Karanam、Stella H. Vincent、Kang Cheng、Mark T. Goulet

  DOI：10.1016/s0960-894x(01)00512-1

  日期：2001.10

  Stereospecific introduction of a methyl group to the indole-3-side chain enhanced activity in our tryptamine-derived series of GnRH receptor antagonists. Further improvements were achieved by variation of the bicyclic amino moiety of the tertiary amide and by adjustment of the tether length to a pyridine or pyridone terminus. These modifications culminated in analogue 24, which had oral activity in a rat model and acceptable oral bioavailability and half-life in dogs and monkeys. (C) 2001 Elsevier Science Ltd. All rights reserved.