(E)-α-methyl-3-thiophenepropenal | 139608-66-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: (E)-α-methyl-3-thiophenepropenal
• 英文别名: 3-(3-Thienyl)-methacrolein；(E)-2-methyl-3-thiophen-3-ylprop-2-enal
• CAS: 139608-66-5
• 化学式: C₈H₈OS
• 分子量: 152.217
• InChiKey: NTMIBBKZXWBQEQ-QPJJXVBHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  45.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-α-methyl-3-thiophenepropenal 在 sodium hydride 、 二异丁基氢化铝 作用下， 以 四氢呋喃 、 二氯甲烷 、 mineral oil 为溶剂， 反应 3.5h， 生成
  参考文献：
  名称：

  SN2″-用不饱和有机硼化合物选择性和对映选择性取代并由含磺酸盐的 NHC-Cu 配合物催化

  摘要：

  公开了第一个广泛适用的 SN2" 选择性和对映选择性催化取代策略。转化由 5.0 mol% 的含磺酸盐的 NHC-Cu 复合物（NHC = N-杂环卡宾）促进，并在市售的烯基-B（pin）（pin = pinacolato）或易于获得的甲硅烷基保护的炔丙基-B(pin)。发现无环、或芳基-、杂芳基-和烷基取代的五-2,4-二烯基磷酸酯，以及仅带有1,2-二取代烯烃或1,2-二取代和三取代烯烃的那些是合适的起始材料。环状磷酸二烯酯也可用作底物。以 51-82% 的收率获得了除 1,3-二烯基外还含有易于官能化的炔丙基部分（来自与丙二烯基-B(pin) 的反应）的产物，84-97% SN2" 选择性，89:11-97:3 E: Z 比和 86:14-98:2 对映体比 (er)。与甲硅烷基保护的炔丙基-B(pin) 化合物反应导致形成相应的甲硅烷基-烯丙基产物，产率 53-89%，SN2" 选择性

  DOI：

  10.1021/jacs.8b10885
• 作为产物：
  描述：

  3-噻吩甲醛 、 丙醛 在 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 以74%的产率得到(E)-α-methyl-3-thiophenepropenal
  参考文献：
  名称：

  Bakers' yeast reduction of thiophenepropaenals. Enantioselective synthesis of (S)-2-methyl-1-alkanols via bakers' yeast mediated reduction of 2-methyl-3-(2-thiophene)propenals

  摘要：

  DOI：

  10.1021/jo00033a028

文献信息

• [EN] ISOXAZOLINE DERIVATIVES AS ANTI-DEPRESSANTS<br/>[FR] DERIVES D'ISOXAZOLINES COMME ANTIDEPRESSEURS
  申请人：JANSSEN PHARMACEUTICA NV

  公开号：WO2002066484A1

  公开（公告）日：2002-08-29

  The invention concerns substituted isoxazolines derivatives according to Formula (I): wherein X = CH?2#191, N-R7, S or O, R1, R2 and R3 are certain specific substituents, Pir is an optionally substituted piperidyl or piperazyl radical and R3 represents an optionally substituted aromatic homocyclic or heterocyclic ring system including a partially or completely hydrogenated hydrocarbon chain of maximum 6 atoms long with which the ring system is attached to the Pir radical and which may contain one or more heteroatoms selected from the group of O, N and S ; a process for their preparation, pharmaceutical compositions comprising them and their use as a medicine, in particular for the treatment of depression and/of anxiety and disorders of body weight. The compounds according to the invention have surprisingly been shown to have a serotonine (5-HT) reuptake inhibitor activity in combination with additional α2-adrenoceptor antagonist activity and show a strong anti-depressant activity without being sedative. Compounds according to the invention are also suitable for treating patients with anxiety disorders and disorders of body weight. The invention also relates to novel combination of substituted isoxazolines derivatives having anti-depressant activity and/or anxiolytic activity and/or body weight control activity with antidepressants, anxiolytics and/or antipsychotics to improve efficacy and/or onset of action.

  该发明涉及按照公式(I)的取代异噁唑啉衍生物：其中X = CH?2#191，N-R7，S或O，R1，R2和R3是特定的取代基，Pir是可选取代的哌啶基或哌嗪基，R3表示可选取代的芳香族同环或杂环环系统，包括最多6个原子长的部分或完全氢化的碳氢链，该环系统与Pir基团连接，并且可能包含从O，N和S组中选择的一个或多个杂原子；一种制备它们的方法，包括它们的制药组合物和它们作为药物的用途，特别是用于治疗抑郁症和/或焦虑症和体重障碍。根据该发明的化合物已经被证明具有血清素（5-HT）重摄取抑制剂活性，结合额外的α2-肾上腺素受体拮抗剂活性，并且表现出强烈的抗抑郁活性，而不会产生镇静作用。根据该发明的化合物也适用于治疗焦虑症和体重障碍的患者。该发明还涉及具有抗抑郁活性和/或抗焦虑活性和/或体重控制活性的取代异噁唑啉衍生物的新组合，与抗抑郁剂，抗焦虑剂和/或抗精神病药物结合以提高疗效和/或作用起始时间。
• TAMARU Y.; YAMADA Y.; YOSHIDA Z., TETRAHEDRON, 1979, 35, NO 3, 329-340
  作者：TAMARU Y.、 YAMADA Y.、 YOSHIDA Z.

  DOI：——

  日期：——
• ISOXAZOLINE DERIVATIVES AS ANTI-DEPRESSANTS
  申请人：JANSSEN PHARMACEUTICA N.V.

  公开号：EP1368358A1

  公开（公告）日：2003-12-10
• Isoxazoline derivatives as anti-depressants
  申请人：——

  公开号：US20040122037A1

  公开（公告）日：2004-06-24

  The invention concerns substituted isoxazolines derivatives according to Formula (I): wherein X=CH?2#191, N—R 7 , S or O, R 1 , R 2 and R 3 are certain specific substituents, Pir is an optionally substituted piperidyl or piperazyl radical and R3 represents an optionally substituted aromatic homocyclic or heterocyclic ring system including a partially or completely hydrogenated hydrocarbon chain of maximum 6 atoms long with which the ring system is attached to the Pir radical and which may contain one or more heteroatoms selected from the group of O, N and S ; a process for their preparation, pharmaceutical compositions comprising them and their use as a medicine, in particular for the treatment of depression and/of anxiety and disorders of body weight. The compounds according to the invention have surprisingly been shown to have a serotonine (5-HT) reuptake inhibitor activity in combination with additional &agr;2-adrenoceptor antagonist activity and show a strong anti-depressant activity without being sedative. Compounds according to the invention arc also suitable for treating patients with anxiety disorders and disorders of body weight. The invention also relates to novel combination of substituted isoxazolines derivatives having anti-depressant activity and/or anxiolytic activity and/or body weight control activity with antidepressants, anxiolytics and/or antipsychotics to improve efficacy and/or onset of action. 1
• US7169786B2
  申请人：——

  公开号：US7169786B2

  公开（公告）日：2007-01-30