methyl exo-2-bromobicyclo<2.2.1>heptane-1-carboxylate | 15023-45-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: methyl exo-2-bromobicyclo<2.2.1>heptane-1-carboxylate
• 英文别名: exo-2-bromonorbornane-1-carboxylic acid；(+/-)-2exo-bromo-norbornane-1-carboxylic acid methyl ester；(+/-)-2exo-Brom-norbornan-1-carbonsaeure-methylester；1-Methoxycarbonyl-2-exo-norbornylbromid；methyl (1S,2S,4R)-2-bromobicyclo[2.2.1]heptane-1-carboxylate
• CAS: 15023-45-7；102450-73-7
• 化学式: C₉H₁₃BrO₂
• 分子量: 233.105
• InChiKey: QFRHEQUPAQAIAD-ACLDMZEESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  methyl exo-2-bromobicyclo<2.2.1>heptane-1-carboxylate 在 potassium tert-butylate 作用下， 以 叔丁醇 为溶剂， 生成 N,N'-Di-(1-norbornenyl)-harnstoff
  参考文献：
  名称：

  Preparation and study of some 1-norbornenyl and norbornenyl-1-carbinyl derivatives

  摘要：

  DOI：

  10.1021/jo01266a047
• 作为产物：
  描述：

  2-exo-Bromobicyclo<2.2.1>heptane-2-endo-carboxaldehyde 在 过氧乙酸 作用下， 生成 methyl exo-2-bromobicyclo<2.2.1>heptane-1-carboxylate
  参考文献：
  名称：

  The Course of Bromination in Bicyclo[2.2.1]heptanecarboxylic Acids; the Observation of Rearrangement During a Reduction of β-Bromoacids

  摘要：

  DOI：

  10.1021/ja01520a039

文献信息

• Cyclopropyl-fused pyrrolidine-based inhibitors of dipeptidyl peptidase IV and method
  申请人：——

  公开号：US20020019411A1

  公开（公告）日：2002-02-14

  Dipeptidyl peptidase IV (DP 4) inhibiting compounds are provided having the formula 1 where x is 0 or 1 and y is 0 or 1 (provided that x=1 when y=0 and x=0 when y=1); n is 0 or 1; X is H or CN; and wherein R 1 , R 2 , R 3 and R 4 are as described herein. A method is also provided for treating diabetes and related diseases, especially Type II diabetes, and other diseases as set out herein, employing such DP 4 inhibitor or a combination of such DP 4 inhibitor and one or more of another antidiabetic agent such as metformin, glyburide, troglitazone, pioglitazone, rosiglitazone and/or insulin and/or one or more of a hypolipidemic agent and/or anti-obesity agent and/or other therapeutic agent.

  提供了具有公式1的抑制二肽基肽酶IV（DP 4）的化合物，其中x为0或1，y为0或1（前提是当y=0时，x=1，当y=1时，x=0）；n为0或1；X为H或CN；其中R1、R2、R3和R4如本文所述。还提供了一种治疗糖尿病和相关疾病，特别是II型糖尿病以及本文中列出的其他疾病的方法，使用这种DP 4抑制剂或这种DP 4抑制剂与另一种或多种抗糖尿病药物（如二甲双胍、格列本脲、曲格列酮、吡格列酮、罗格列酮和/或胰岛素）的组合，以及一种或多种降脂药物和/或抗肥胖药物和/或其他治疗药物。
• From norbornane-based nucleotide analogs locked in South conformation to novel inhibitors of feline herpes virus
  作者：Milan Dejmek、Hubert Hřebabecký、Michal Šála、Martin Dračínský、Eliška Procházková、Pieter Leyssen、Johan Neyts、Jan Balzarini、Radim Nencka

  DOI：10.1016/j.bmc.2014.04.004

  日期：2014.6

  A synthetic route toward a series of unique cyclic nucleoside phosphonates locked in South conformation is described. The desired conformation is stabilized by a substitution of the sugar moiety by bicyclo[2.2.1]heptane (norbornane) bearing a purine or pyrimidine nucleobase in the bridgehead position. Although the final phosphonate derivatives are devoid of any significant antiviral activity probably

  描述了合成路线的一系列独特的环状核苷膦酸酯锁定在南构象。通过在桥头位置带有嘌呤或嘧啶核碱基的双环[2.2.1]庚烷（降冰片烷）取代糖部分，可以稳定所需的构象。尽管最终的膦酸酯衍生物可能由于不利的构象特性而没有任何重要的抗病毒活性，但一些中间体及其类似物对猫疱疹病毒显示出令人惊讶的活性。由于这些化合物不具有适当的羟甲基官能团，因此无法进行磷酸化并随后掺入多核苷酸链中，这些化合物似乎是通过一种未知的新作用机制起作用，并可能代表这种广泛传播的猫感染的核苷和核苷酸治疗药物的新的可能替代品。许多衍生物还对柯萨奇病毒B3和B4发挥了重要的抗病毒活性。
• Palladium/Norbornene‐Catalyzed Direct Vicinal Di‐Carbo‐Functionalization of Indoles: Reaction Development and Mechanistic Study
  作者：Xin Liu、Yun Zhou、Xiaotian Qi、Renhe Li、Peng Liu、Guangbin Dong

  DOI：10.1002/anie.202310697

  日期：2023.10.23

  Methods that can simultaneously install multiple different functional groups to heteroarenes via C−H functionalizations are valuable for complex molecule synthesis, which, however, remain challenging to realize. Here we report the development of vicinal di‐carbo‐functionalization of indoles in a site‐ and regioselective manner, enabled by the palladium/norbornene (Pd/NBE) cooperative catalysis. The reaction is initiated by the Pd(II)‐mediated C3‐metalation and specifically promoted by the C1‐substituted NBEs. The mild, scalable, and robust reaction conditions allow for a good substrate scope and excellent functional group tolerance. The resulting C2‐arylated C3‐alkenylated indoles can be converted to diverse synthetically useful scaffolds. The combined experimental and computational mechanistic study reveals the unique role of the C1‐substituted NBE in accelerating the turnover‐limiting oxidative addition step.

  摘要能够通过 C-H 功能化同时在杂环烯上安装多个不同官能团的方法对于复杂分子的合成非常有价值，然而实现这种方法仍然具有挑战性。在此，我们报告了通过钯/降冰片烯（Pd/NBE）协同催化，以位点选择性和区域选择性的方式对吲哚进行邻位二羧基官能化的研究进展。反应由 Pd(II) 介导的 C3 金属化引发，并由 C1 取代的 NBE 特别促进。反应条件温和、可扩展且稳健，因而具有良好的底物范围和优异的官能团耐受性。生成的 C2 芳基化 C3 烯基吲哚可转化为多种有用的合成支架。实验和计算机理的综合研究揭示了 C1 取代的 NBE 在加速限制周转的氧化加成步骤中的独特作用。
• Cyclopropyl-fused pyrrolidine-based inhibitors of dipeptidyl peptidase IV, process for their preparation and their use
  申请人：Bristol-Myers Squibb Company

  公开号：EP1559710A2

  公开（公告）日：2005-08-03

  Dipeptidyl peptidase IV (DP 4) inhibiting compounds are provided having the formula (I) where x is 0 or 1 and y is 0 or 1 (provided that x = 1 when y = 0 and x = 0 when y = 1); n is 0 or 1; X is H; and wherein R1, R2, R3 and R4 are as described herein. A method is also provided for treating diabetes and related diseases, especially Type II diabetes, and other diseases as set out herein, employing such DP 4 inhibitor or a combination of such DP 4 inhibitor and one or more of another antidiabetic agent such as metformin, glyburide, troglitazone, pioglitazone, rosiglitazone and/or insulin and/or one or more of a hypolipidemic agent and/or anti-obesity and/or other therapeutic agent.

  提供了具有式（I）的二肽基肽酶 IV（DP 4）抑制化合物 其中 x 为 0 或 1，y 为 0 或 1（条件是当 y = 0 时 x = 1，当 y = 1 时 x = 0）；n 为 0 或 1；X 为 H；其中 R1、R2、R3 和 R4 如本文所述。还提供了一种治疗糖尿病和相关疾病，特别是II型糖尿病，以及本文所述的其他疾病的方法，该方法采用了这种DP 4抑制剂或这种DP 4抑制剂与另一种或多种抗糖尿病剂如二甲双胍、甘氟脲、曲格列酮、吡格列酮、罗格列酮和/或胰岛素和/或一种或多种降血脂剂和/或抗肥胖和/或其他治疗剂的组合。
• N-Protected amino hydroxy adamantane carboxylic acid and process for its preparation
  申请人：Bristol-Myers Squibb Company

  公开号：EP2272825A2

  公开（公告）日：2011-01-12

  Dipeptidyl peptidase IV (DP 4) inhibiting compounds are provided having the formula (I) where x is 0 or 1 and y is 0 or 1 (provided that x = 1 when y = 0 and x = 0 when y = 1); n is 0 or 1; X is H; and wherein R1, R2, R3 and R4 are as described herein. A method is also provided for treating diabetes and related diseases, especially Type II diabetes, and other diseases as set out herein, employing such DP 4 inhibitor or a combination of such DP 4 inhibitor and one or more of another antidiabetic agent such as metformin, glyburide, troglitazone, pioglitazone, rosiglitazone and/or insulin and/or one or more of a hypolipidemic agent and/or anti-obesity and/or other therapeutic agent.

  提供了具有式（I）的二肽基肽酶 IV（DP 4）抑制化合物 其中 x 为 0 或 1，y 为 0 或 1（条件是当 y = 0 时 x = 1，当 y = 1 时 x = 0）；n 为 0 或 1；X 为 H；其中 R1、R2、R3 和 R4 如本文所述。还提供了一种治疗糖尿病和相关疾病，特别是II型糖尿病，以及本文所述的其他疾病的方法，该方法采用了这种DP 4抑制剂或这种DP 4抑制剂与另一种或多种抗糖尿病剂如二甲双胍、甘氟脲、曲格列酮、吡格列酮、罗格列酮和/或胰岛素和/或一种或多种降血脂剂和/或抗肥胖和/或其他治疗剂的组合。