N-allyl-3-butenethioamide | 827320-17-2

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫代酰胺
• 英文名称: N-allyl-3-butenethioamide
• 英文别名: 3-Butenethioamide, N-2-propenyl-；N-prop-2-enylbut-3-enethioamide
• CAS: 827320-17-2
• 化学式: C₇H₁₁NS
• mdl: MFCD19225831
• 分子量: 141.237
• InChiKey: KTFLNWSKCFPHAF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  9
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.285
• 拓扑面积：
  44.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  天然芥菜籽油 、 烯丙基溴化镁 以 四氢呋喃 、 乙醚 为溶剂， 反应 1.5h， 以88%的产率得到N-allyl-3-butenethioamide
  参考文献：
  名称：

  Reactions of Heterocumulenes with Organometallic Reagents: IX. Synthesis and Rearrangements of N-Allyl-and N-[2-(Vinyloxy)ethyl]-3-butenethioamides and -1-(methylsulfanyl)-3-buten-1-imines

  摘要：

  Reactions of allyl and 2-(vinyloxy)ethyl isothiocyanates with alyylmagnesium bromide (THF-Et2O, 20-30degreesC, 1-3 h) after hydrolysis or alkylation of adducts afforded respectively N-allyl- and N-[2-(vinyloxy)ethyl]3-butenethioamides or N-allyl- and N-[2-(vinyloxy)ethyl]-1-(methylmercapto)-3-buten-1-imines The reaction carried out in ethyl ether yielded instead of N-allyl-3-butenethioamide its isomer N-allyl-2-butenethioamide that cleanly isomerized in the system KOH-DMSO-H2O into N-(I-propenyl)-2-butenethioamide. N-[2-(vinyloxy)ethyl]-3-butenethioamide suffers a prototropic rearrangement into N-[2-(vinyloxy)ethyl]-2-butenethioamide only in the system t-BuOK-DMSO.

  DOI：

  10.1023/b:rujo.0000034938.57063.55

文献信息

• ETHERS, SECONDARY AMINES AND DERIVATIVES THEREOF AS MODULATORS OF THE 5-HT2A SEROTONIN RECEPTOR USEFUL FOR THE TREATMENT OF DISORDERS RELATED THERETO
  申请人：TEEGARDEN BRADLEY

  公开号：US20120295938A1

  公开（公告）日：2012-11-22

  The present invention pertains to certain compounds of Formula (Ia) and pharmaceutical compositions thereof that modulate the activity of the 5-HT2A serotonin receptor. Compounds and pharmaceutical compositions thereof are directed to methods useful in the treatment of platelet aggregation, coronary artery disease, myocardial infarction, transient ischemic attack, angina, stroke, atrial fibrillation, blood clot formation, asthma or symptoms thereof, agitation or a symptom thereof, behavioral disorders, drug induced psychosis, excitative psychosis, Gilles de la Tourette's syndrome, manic disorder, organic or NOS psychosis, psychotic disorder, psychosis, acute schizophrenia, chronic schizophrenia, NOS schizophrenia and related disorders, and sleep disorders, sleep disorders, diabetic-related disorders, progressive multifocal leukoencephalopathy and the like. The present invention also relates to the methods for the treatment of 5-HT2A serotonin receptor associated disorders in combination with other pharmaceutical agents administered separately or together.

  本发明涉及公式（Ia）的某些化合物及其制药组合物，其调节5-HT2A血清素受体的活性。该化合物和制药组合物针对的方法有助于治疗血小板聚集、冠状动脉疾病、心肌梗死、暂时性脑缺血发作、心绞痛、中风、心房颤动、血栓形成、哮喘或其症状、激动或其症状、行为障碍、药物诱发的精神病、兴奋性精神病、Gilles de la Tourette综合症、躁狂障碍、器质性或NOS精神病、精神病、急性精神分裂症、慢性精神分裂症、NOS精神分裂症及相关疾病、睡眠障碍、糖尿病相关疾病、进行性多灶性白质脑病等。本发明还涉及与其他药物分别或联合使用治疗5-HT2A血清素受体相关疾病的方法。
• US8680119B2
  申请人：——

  公开号：US8680119B2

  公开（公告）日：2014-03-25
• Reactions of Heterocumulenes with Organometallic Reagents: IX. Synthesis and Rearrangements of N-Allyl-and N-[2-(Vinyloxy)ethyl]-3-butenethioamides and -1-(methylsulfanyl)-3-buten-1-imines
  作者：L. L. Dmitrieva、L. P. Nikitina、A. I. Albanov、G. I. Sarapulova、N. A. Nedolya、L. Brandsma

  DOI：10.1023/b:rujo.0000034938.57063.55

  日期：2004.2

  Reactions of allyl and 2-(vinyloxy)ethyl isothiocyanates with alyylmagnesium bromide (THF-Et2O, 20-30degreesC, 1-3 h) after hydrolysis or alkylation of adducts afforded respectively N-allyl- and N-[2-(vinyloxy)ethyl]3-butenethioamides or N-allyl- and N-[2-(vinyloxy)ethyl]-1-(methylmercapto)-3-buten-1-imines The reaction carried out in ethyl ether yielded instead of N-allyl-3-butenethioamide its isomer N-allyl-2-butenethioamide that cleanly isomerized in the system KOH-DMSO-H2O into N-(I-propenyl)-2-butenethioamide. N-[2-(vinyloxy)ethyl]-3-butenethioamide suffers a prototropic rearrangement into N-[2-(vinyloxy)ethyl]-2-butenethioamide only in the system t-BuOK-DMSO.