tert-butyl 3-oxo-6-azabicyclo[3.1.1]heptane-6-carboxylate | 1246281-86-6

• 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: tert-butyl 3-oxo-6-azabicyclo[3.1.1]heptane-6-carboxylate
• CAS: 1246281-86-6
• 化学式: C₁₁H₁₇NO₃
• 分子量: 211.261
• InChiKey: MXCNJPMLNRBZJB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  tert-butyl 3-oxo-6-azabicyclo[3.1.1]heptane-6-carboxylate 在 sodium tetrahydroborate 、 偶氮二甲酸二异丙酯 、 三苯基膦 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 15.0h， 生成 cis-tert-butyl 3-((4-nitrobenzoyl)oxy)-6-azabicyclo[3.1.1]heptane-6-carboxylate
  参考文献：
  名称：

  3-取代的 6-氮杂双环[3.1.1]庚烷：用于药物发现的非经典哌啶电子等排体

  摘要：

  使用现成的批量试剂大规模合成了哌啶的高级类似物和托烷的较小同系物 — 3-取代的 6-氮杂双环[3.1.1]庚烷。该方法的关键步骤涉及丙二酸与顺式-2,4-双(甲磺氧基甲基)氮杂环丁烷-1-羧酸酯的双烷基化反应，进而可以轻松制备高达1千克的规模。水解后，得到N -Boc-6-氮杂双环[3.1.1]庚烷-3,3-二甲酸（单次最多400 g），将其用作制备所有标题的通用中间体积木。特别是，该中间体的 Pb(OAc) 4介导的氧化脱羧得到 2,6-亚甲基哌啶酮衍生物（高达 400 g 规模），而单脱羧得到N -Boc-6-氮杂双环[3.1.1]庚烷-3-羧基酸作为顺式和反式非对映异构体的易于分离的混合物（最多 100 克规模）。进一步的官能团转化得到非对映纯的顺式和反式N -Boc-单保护的二胺和氨基醇。使用退出矢量参数（EVP）的分子结构分析表明，3-取代的6-氮杂双环[3.1.1]庚烷的顺式异构体是常见1

  DOI：

  10.1021/acs.joc.4c00326
• 作为产物：
  描述：

  trans-tert-butyl 3-hydroxy-6-azabicyclo[3.1.1]heptane-6-carboxylate 在 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 为溶剂， 生成 tert-butyl 3-oxo-6-azabicyclo[3.1.1]heptane-6-carboxylate
  参考文献：
  名称：

  [EN] COMPOUNDS, COMPOSITIONS, AND METHODS
  [FR] COMPOSÉS, COMPOSITIONS ET PROCÉDÉS

  摘要：

  The present disclosure relates generally to small molecule inhibitors of Sterile Alpha and TIR Motif containing 1 (SARM1) protein, or a pharmaceutically acceptable salt, isotopically enriched analog, stereoisomer, mixture of stereoisomers, or prodrug thereof, methods of making and intermediates thereof, and methods of using thereof.

  公开号：

  WO2023240084A2

文献信息

• INDOLE AND INDOLINE DERIVATIVES AND METHODS OF USE THEREOF
  申请人：Schrimpf Michael R.

  公开号：US20100249105A1

  公开（公告）日：2010-09-30

  The present application relates to indole and indoline derivatives of formula (I), (II), (III), (IV), (V), or (VI) wherein a, R 1 , R 2 , R 3 , R 4 , R 5 , U, V, W, X, Y, and Z are as defined in the specification. The present application also relates to compositions comprising such compounds, and methods of treating disease conditions using such compounds and compositions, and methods for identifying such compounds.

  本申请涉及公式（I），（II），（III），（IV），（V）或（VI）的吲哚和吲哚啉衍生物，其中a，R1，R2，R3，R4，R5，U，V，W，X，Y和Z如规范中所定义。本申请还涉及包含这种化合物的组合物，使用这种化合物和组合物治疗疾病状态的方法，以及识别这种化合物的方法。
• [1,2,4]triazolo[1,5and#8208;A]pyrimidine compounds as PDE2 inhibitors
  申请人：Janssen Pharmaceutica NV

  公开号：US10947242B2

  公开（公告）日：2021-03-16

  The present invention relates to novel [1,2,4]triazolo[1,5-a]pyrimidin-yl derivatives as inhibitors of phosphodiesterase 2 (PDE2). The invention is also directed to pharmaceutical compositions comprising the compounds, to processes for preparing such compounds and compositions, and to the use of such compounds and compositions for the prevention and treatment of disorders in which PDE2 is involved, such as neurological and psychiatric disorders.

  本发明涉及作为磷酸二酯酶 2（PDE2）抑制剂的新型[1,2,4]三唑并[1,5-a]嘧啶基衍生物。本发明还涉及包含这些化合物的药物组合物、制备这些化合物和组合物的工艺，以及使用这些化合物和组合物预防和治疗涉及 PDE2 的疾病，如神经和精神疾病。
• [1,2,4]TRIAZOLO[1,5-A]PYRIMIDINE DERIVATIVES AS PDE2 INHIBITORS
  申请人：Janssen Pharmaceutica NV

  公开号：EP3535267B1

  公开（公告）日：2020-12-30
• BICYCLIC HETEROCYCLE DERIVATIVES AND METHODS OF USE THEREOF
  申请人：Neelamkavil Santhosh Francis

  公开号：US20110166167A1

  公开（公告）日：2011-07-07

  The present invention relates to Bicyclic Heterocycle Derivatives, compositions comprising a Bicyclic Heterocycle Derivative, and methods of using the Bicyclic Heterocycle Derivatives for treating or preventing obesity, diabetes, a diabetic complication, a metabolic disorder, a cardiovascular disease or a disorder related to the activity of a G protein-coupled receptor (GPCR) in a patient. The compounds are of structure (I).
• [1,2,4]TRIAZOLO[1,5‐A]PYRIMIDINE COMPOUNDS AS PDE2 INHIBITORS
  申请人：Janssen Pharmaceutica NV

  公开号：US20190276462A1

  公开（公告）日：2019-09-12

  The present invention relates to novel [1,2,4]triazolo[1,5-a]pyrimidin-yl derivatives as inhibitors of phosphodiesterase 2 (PDE2). The invention is also directed to pharmaceutical compositions comprising the compounds, to processes for preparing such compounds and compositions, and to the use of such compounds and compositions for the prevention and treatment of disorders in which PDE2 is involved, such as neurological and psychiatric disorders.