3-(phenyl)-5-propyl-1H-pyrazole | 1231309-29-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3-(phenyl)-5-propyl-1H-pyrazole
• 英文别名: 3-phenyl-5-propyl-1H-pyrazole
• CAS: 1231309-29-7
• 化学式: C₁₂H₁₄N₂
• 分子量: 186.257
• InChiKey: MDMHACNYJHVIGD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  28.7
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-(phenyl)-5-propyl-1H-pyrazole 在 溴 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 生成 4-bromo-3-phenyl-5-propyl-1H-pyrazole
  参考文献：
  名称：

  [EN] PYRAZOLYL SUBSTITUTED CARBONIC ACID DERIVATIVES AS MODULATORS OF THE PROSTACYCLIN (PGI2) RECEPTOR USEFUL FOR THE TREATMENT OF DISORDERS RELATED THERETO
  [FR] DÉRIVÉS D'ACIDE CARBONIQUE SUBSTITUÉS PAR PYRAZOLYLE EN TANT QUE MODULATEURS DU RÉCEPTEUR DE LA PROSTACYCLINE PGI2 ADAPTÉS AU TRAITEMENT DE TROUBLES LE FAISANT INTERVENIR

  摘要：

  Formula Ia的吡唑衍生物及其药物组成物，可调节PGI2受体的活性。本发明的化合物和药物组成物用于治疗以下疾病：肺动脉高压（PAH）及相关疾病；血小板聚集；冠状动脉疾病；心肌梗死；短暂性缺血性发作；心绞痛；中风；缺血再灌注损伤；再狭窄；心房颤动；血栓形成在冠状动脉成形术或冠状动脉旁路手术个体中或在患有心房颤动的个体中；动脉粥样硬化；动脉粥样血栓形成；哮喘或其症状；糖尿病相关疾病，如糖尿病周围神经病变、糖尿病肾病或糖尿病视网膜病变；青光眼或其他眼睛异常眼压疾病；高血压；炎症；牛皮癣；银屑病性关节炎；类风湿性关节炎；克罗恩病；移植排斥；多发性硬化症；系统性红斑狼疮（SLE）；溃疡性结肠炎；缺血再灌注损伤；再狭窄；动脉粥样硬化；痤疮；1型糖尿病；2型糖尿病；败血症；慢性阻塞性肺疾病（COPD）。

  公开号：

  WO2010068242A1
• 作为产物：
  描述：

  1-苯基己-1-炔-3-酮 在 乙醇 、 sodium acetate 、 硫酸肼 作用下， 生成 3-(phenyl)-5-propyl-1H-pyrazole
  参考文献：
  名称：

  Moureu; Brachin, Bulletin de la Societe Chimique de France, 1905, vol. <3> 33, p. 144

  摘要：

  DOI：

文献信息

• An Efficient Synthesis of Substituted Pyrazoles from One-Pot Reaction of Ketones, Aldehydes, and Hydrazine Monohydrochloride
  作者：Vit Lellek、Cheng-yi Chen、Wanggui Yang、Jie Liu、Xuebao Ji、Roger Faessler

  DOI：10.1055/s-0036-1591941

  日期：2018.5

  hydrazine monohydrochloride readily formed pyrazoline intermediates under mild conditions. Oxidation of pyrazolines, in situ, employing bromine afforded a wide variety of pyrazoles. The methodology offers a fast, and often chromatography-free protocol for the synthesis of 3,4,5-substituted pyrazoles in good to excellent yields. Alternatively, a more benign oxidation protocol affords 3,5-disubstituted or

  开发了一种高效、单锅且无金属的制备多克规模的 3,5-二取代和 3,4,5-三取代吡唑的方法。在温和条件下，酮、醛和肼单盐酸盐的一锅缩合容易形成吡唑啉中间体。使用溴原位氧化吡唑啉得到多种吡唑。该方法为合成 3,4,5-取代吡唑的 3,4,5-取代吡唑类化合物提供了一种快速且通常无需色谱的方案，收率非常好。或者，通过简单地在 DMSO 中在氧气下加热吡唑啉，更温和的氧化方案提供 3,5-二取代或 3,4,5-三取代的吡唑。
• Synthesis of 3,5-Disubstituted-1H-Pyrazoles from Acid Chlorides, Alkynes, and Hydrazine in the Presence of Silica-Supported-Zinc Bromide
  作者：Ali Keivanloo、Mohammad Bakherad、Shahrzad Samangooei

  DOI：10.3184/174751915x14382642961716

  日期：2015.8

  An efficient one-pot palladium- and copper-free procedure has been developed for a convenient synthesis of 3,5 -disubstituted-1H-pyrazoles from various acid chlorides, terminal alkynes and hydrazine by a coupling reaction and cyclocondensation sequence. Acid chlorides react with terminal alkynes in the presence of silica-supported-zinc bromide to give α,β-unsaturated ynones, and in situ conversion

  已开发出一种高效的一锅式无钯和无铜工艺，可通过偶联反应和环缩合顺序从各种酰氯、末端炔烃和肼方便地合成 3,5-二取代-1H-吡唑。在二氧化硅负载的溴化锌存在下，酰氯与末端炔烃反应生成 α,β-不饱和炔酮，并通过肼环缩合反应原位转化为吡唑。
• PYRAZOLYL SUBSTITUTED CARBONIC ACID DERIVATIVES AS MODULATORS OF THE PROSTACYCLIN (PGI2) RECEPTOR USEFUL FOR THE TREATMENT OF DISORDERS RELATED THERETO
  申请人：Tran Thuy-Anh

  公开号：US20110224262A1

  公开（公告）日：2011-09-15

  Pyrazole derivatives of Formula Ia and pharmaceutical compositions thereof that modulate the activity of the PGI2 receptor. Compounds of the present invention and pharmaceutical compositions thereof are directed to methods useful in the treatment of: pulmonary arterial hypertension (PAH) and related disorders; platelet aggregation; coronary artery disease; myocardial infarction; transient ischemic attack; angina; stroke; ischemia-reperfusion injury; restenosis; atrial fibrillation; blood clot formation in an angioplasty or coronary bypass surgery individual or in an individual suffering from atrial fibrillation; atherosclerosis; atherothrombosis; asthma or a symptom thereof; a diabetic-related disorder such as diabetic peripheral neuropathy, diabetic nephropathy or diabetic retinopathy; glaucoma or other disease of the eye with abnormal intraocular pressure; hypertension; inflammation; psoriasis; psoriatic arthritis; rheumatoid arthritis; Crohn's disease; transplant rejection; multiple sclerosis; systemic lupus erythematosus (SLE); ulcerative colitis; ischemia-reperfusion injury; restenosis; atherosclerosis; acne; type 1 diabetes; type 2 diabetes; sepsis; and chronic obstructive pulmonary disorder (COPD).

  公式Ia的吡唑衍生物及其制药组合物，用于调节PGI2受体的活性。本发明的化合物和制药组合物用于治疗以下疾病的有用方法：肺动脉高压（PAH）及相关疾病；血小板聚集；冠状动脉疾病；心肌梗死；短暂性脑缺血发作；心绞痛；中风；缺血再灌注损伤；再狭窄；房颤的血栓形成或在患有房颤的个体中的冠状动脉成形术或冠状动脉旁路手术；动脉粥样硬化；动脉粥样血栓形成；哮喘或其症状；与糖尿病相关的疾病，如糖尿病周围神经病、糖尿病肾病或糖尿病视网膜病变；青光眼或其他眼部异常眼压的疾病；高血压；炎症；牛皮癣；银屑病性关节炎；类风湿性关节炎；克罗恩病；移植排斥；多发性硬化症；系统性红斑狼疮（SLE）；溃疡性结肠炎；再灌注损伤；再狭窄；动脉粥样硬化；痤疮；1型糖尿病；2型糖尿病；败血症；慢性阻塞性肺疾病（COPD）。
• Pyrazolyl substituted carbonic acid derivatives as modulators of the prostacyclin (PGI2) receptor useful for the treatment of disorders related thereto
  申请人：Arena Pharmaceuticals, Inc.

  公开号：US09012478B2

  公开（公告）日：2015-04-21

  Pyrazole derivatives of Formula Ia and pharmaceutical compositions thereof that modulate the activity of the PGI2 receptor. Compounds of the present invention and pharmaceutical compositions thereof are directed to methods useful in the treatment of: pulmonary arterial hypertension (PAH) and related disorders; platelet aggregation; coronary artery disease; myocardial infarction; transient ischemic attack; angina; stroke; ischemia-reperfusion injury; restenosis; atrial fibrillation; blood clot formation in an angioplasty or coronary bypass surgery individual or in an individual suffering from atrial fibrillation; atherosclerosis; atherothrombosis; asthma or a symptom thereof; a diabetic-related disorder such as diabetic peripheral neuropathy, diabetic nephropathy or diabetic retinopathy; glaucoma or other disease of the eye with abnormal intraocular pressure; hypertension; inflammation; psoriasis; psoriatic arthritis; rheumatoid arthritis; Crohn's disease; transplant rejection; multiple sclerosis; systemic lupus erythematosus (SLE); ulcerative colitis; ischemia-reperfusion injury; restenosis; atherosclerosis; acne; type 1 diabetes; type 2 diabetes; sepsis; and chronic obstructive pulmonary disorder (COPD).

  公式Ia的吡唑衍生物及其药物组成物可以调节PGI2受体的活性。本发明的化合物和药物组成物适用于以下治疗方法：肺动脉高压（PAH）及相关疾病；血小板聚集；冠状动脉疾病；心肌梗塞；短暂性脑缺血发作；心绞痛；中风；缺血再灌注损伤；再狭窄；房颤；血栓形成在血管成形术或冠状动脉旁路手术患者或患有房颤的个体中；动脉粥样硬化；动脉粥样硬化性血栓形成；哮喘或其症状；糖尿病相关疾病，如糖尿病周围神经病、糖尿病肾病或糖尿病视网膜病变；青光眼或其他眼部异常眼压疾病；高血压；炎症；银屑病；银屑病性关节炎；类风湿性关节炎；克罗恩病；移植排斥反应；多发性硬化症；系统性红斑狼疮（SLE）；溃疡性结肠炎；缺血再灌注损伤；再狭窄；动脉粥样硬化；痤疮；1型糖尿病；2型糖尿病；败血症；慢性阻塞性肺疾病（COPD）。
• Andre, Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1912, vol. 155, p. 53
  作者：Andre

  DOI：——

  日期：——