1-丁基-4-碘-1H-吡唑 | 918487-10-2

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 芳基卤化物
• 中文名称: 1-丁基-4-碘-1H-吡唑
• 英文名称: 1-butyl-4-iodo-1H-pyrazole
• 英文别名: 4-iodo-1-butylpyrazole；1-butyl-4-iodopyrazole
• CAS: 918487-10-2
• 化学式: C₇H₁₁IN₂
• 分子量: 250.082
• InChiKey: QPURVXUEGIIVDN-UHFFFAOYSA-N

物化性质

• 沸点：
  271.5±13.0 °C(Predicted)
• 密度：
  1.68±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  10
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  17.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-丁基-4-碘-1H-吡唑 在 bis-triphenylphosphine-palladium(II) chloride 、 potassium permanganate 、 copper(l) iodide 、 水 、 碳酸氢钠 、 magnesium sulfate 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 生成
  参考文献：
  名称：

  New pyrazolyl and thienyl aminohydantoins as potent BACE1 inhibitors: Exploring the S2′ region

  摘要：

  The proteolytic enzyme beta-secretase (BACE1) plays a central role in the synthesis of the pathogenic beta-amyloid in Alzheimer's disease. SAR studies of the S2' region of the BACE1 ligand binding pocket with pyrazolyl and thienyl P2' side chains are reported. These analogs exhibit low nanomolar potency for BACE1, and demonstrate >50-to 100-fold selectivity for the structurally related aspartyl proteases BACE2 and cathepsin D. Small groups attached at the nitrogen of the P2' pyrazolyl moiety, together with the P3 pyrimidine nucleus projecting into the S3 region of the binding pocket, are critical components to ligand's potency and selectivity. P2' thiophene side chain analogs are highly potent BACE1 inhibitors with excellent selectivity against cathepsin D, but only modest selectivity against BACE2. The cell-based activity of these new analogs tracked well with their increased molecular binding with EC50 values of 0.07-0.2 mu M in the ELISA assay for the most potent analogs. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.07.057
• 作为产物：
  描述：

  4-碘吡唑 、 正溴丁烷 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 以100%的产率得到1-丁基-4-碘-1H-吡唑
  参考文献：
  名称：

  [EN] ORGANIC COMPOUNDS
  [FR] COMPOSÉS ORGANIQUES

  摘要：

  揭示了新型苯并呋喃衍生物。这些衍生物具有S1P1受体活性和/或疾病修饰活性，并可用于治疗与动物和/或人类的免疫、血管和神经系统相关的疾病或症状。

  公开号：

  WO2014063199A1

文献信息

• [EN] S1P RECEPTORS MODULATORS AND THEIR USE THEREOF<br/>[FR] MODULATEURS DES RÉCEPTEURS S1P ET LEUR UTILISATION
  申请人：AKAAL PHARMA PTY LTD

  公开号：WO2010043000A1

  公开（公告）日：2010-04-22

  The invention relates to novel compounds that have S1P receptor modulating activity. Further, the invention relates to a pharmaceutical comprising at least one compound of the invention for the treatment of diseases and/or conditions caused by or associated with inappropriate S1P receptor modulating activity or expression, for example, autoimmune response. A further aspect of the invention relates to the use of a pharmaceutical comprising at least one compound of the invention for the manufacture of a medicament for the treatment of diseases and/or conditions caused by or associated with inappropriate S1P receptor modulating activity or expression such as autoimmune response.

  这项发明涉及具有S1P受体调节活性的新化合物。此外，该发明涉及包括本发明中至少一种化合物的药物，用于治疗由不当的S1P受体调节活性或表达引起或相关的疾病和/或病况，例如自身免疫反应。该发明的另一个方面涉及使用包括本发明中至少一种化合物的药物制造药物，用于治疗由不当的S1P受体调节活性或表达引起或相关的疾病和/或病况，如自身免疫反应。
• Pd-Catalyzed C–H Annulation of Five-Membered Heteroaryl Halides with Norbornene Derivatives
  作者：Birakishore Padhi、Geunhee Kang、Eunmin Kim、Jeongmin Ha、Hyun Tae Kim、Jeewoo Lim、Jung Min Joo

  DOI：10.1021/acscatal.9b05177

  日期：2020.2.7

  Complementary to Catellani-type reactions and 1:1 coupling of six-membered halo(hetero)arenes and norbornene (NBE) derivatives, Pd-catalyzed 1:2 coupling of five-membered haloheteroarenes with NBEs was achieved to afford rigid nonplanar heterocycles. Pyrazole, thiophene, furan, and indole underwent exo- and trans-selective annulation. Two strained alkene groups of the resulting products were further

  互补于Catellani型反应和六元卤代（杂）芳烃与降冰片烯（NBE）衍生物的1：1偶联，Pd催化五元卤代芳烃与NBE的1：2偶联以提供刚性的非平面杂环。吡唑，噻吩，呋喃和吲哚进行了exo-和反选择环空。进一步处理所得产物的两个应变烯基，得到1-烷基吲唑和梯形聚合物。杂芳烃的类型和卤化物的位置以及配体和碱的选择对于在C–H环化反应和Catellani反应之间设置偏好至关重要，这对于开发Pd催化，NBE介导的杂芳烃反应非常有用。
• Ligand-controlled Regiodivergent C−H Alkenylation of Pyrazoles and its Application to the Synthesis of Indazoles
  作者：Hyun Tae Kim、Hyeri Ha、Geunhee Kang、Og Soon Kim、Ho Ryu、Abul Kalam Biswas、Sang Min Lim、Mu-Hyun Baik、Jung Min Joo

  DOI：10.1002/anie.201709162

  日期：2017.12.18

  Regioselective C4‐, C5‐, and di‐alkenylations of pyrazoles were achieved. An electrophilic Pd catalyst generated by trifluoroacetic acid (TFA) and 4,5‐diazafluoren‐9‐one (DAF) leads to C4‐alkenylation, whereas KOAc and mono‐protected amino acid (MPAA) ligand Ac‐Val‐OH give C5‐alkenylation. A combination of palladium acetate, silver carbonate, and pivalic acid affords dialkenylation products. Annulation

  实现了吡唑的区域选择性C4-，C5-和二烯基化。由三氟乙酸（TFA）和4,5-二氮杂芴-9-one（DAF）生成的亲电Pd催化剂导致C4-烯基化，而KOAc和单保护氨基酸（MPAA）配体Ac-Val-OH则使C5-烯基化。乙酸钯，碳酸银和新戊酸的组合提供二烯基化产物。通过顺序的烯基化，热6π-电环化和氧化进行环化，得到官能化的吲唑。这种全面的策略极大地扩展了易于获得的吡唑和吲唑衍生物的范围，从而使吡唑和其他杂芳族体系的有用的区域发散性CH功能化。
• S1P Receptors Modulators and Their Use Thereof
  申请人：Gill Gurmit S.

  公开号：US20110318388A1

  公开（公告）日：2011-12-29

  The invention relates to novel compounds that have S1P receptor modulating activity. Further, the invention relates to a pharmaceutical comprising at least one compound of the invention for the treatment of diseases and/or conditions caused by or associated with inappropriate S1P receptor modulating activity or expression, for example, autoimmune response. A further aspect of the invention relates to the use of a pharmaceutical comprising at least one compound of the invention for the manufacture of a medicament for the treatment of diseases and/or conditions caused by or associated with inappropriate S1P receptor modulating activity or expression such as autoimmune response.

  本发明涉及具有S1P受体调节活性的新化合物。此外，本发明涉及包括本发明中至少一种化合物的药物，用于治疗由不适当的S1P受体调节活性或表达引起或相关的疾病和/或病情，例如自身免疫反应。本发明的另一个方面涉及使用包括本发明中至少一种化合物的药物制造药物，用于治疗由不适当的S1P受体调节活性或表达引起或相关的疾病和/或病情，例如自身免疫反应。
• S1P receptors modulators and their use thereof
  申请人：Gill Gurmit S.

  公开号：US08592399B2

  公开（公告）日：2013-11-26

  The invention relates to novel compounds that have S1P receptor modulating activity. Further, the invention relates to a pharmaceutical comprising at least one compound of the invention for the treatment of diseases and/or conditions caused by or associated with inappropriate S1P receptor modulating activity or expression, for example, autoimmune response. A further aspect of the invention relates to the use of a pharmaceutical comprising at least one compound of the invention for the manufacture of a medicament for the treatment of diseases and/or conditions caused by or associated with inappropriate S1P receptor modulating activity or expression such as autoimmune response.

  这项发明涉及具有S1P受体调节活性的新化合物。此外，该发明涉及一种制药组合物，该组合物包括本发明中的至少一种化合物，用于治疗由或与不适当的S1P受体调节活性或表达有关的疾病和/或病情，例如自身免疫反应。该发明的另一个方面涉及使用包括本发明中的至少一种化合物的制药组合物制造药物，用于治疗由或与不适当的S1P受体调节活性或表达有关的疾病和/或病情，例如自身免疫反应。