2-(3-thienyl)allylamine | 99605-74-0

• 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: 2-(3-thienyl)allylamine
• 英文别名: β-methylene-3-thiopheneethanamine；3-amino-2-(3'-thienyl)propene；2-Thiophen-3-yl-allylamine；2-thiophen-3-ylprop-2-en-1-amine
• CAS: 99605-74-0
• 化学式: C₇H₉NS
• mdl: MFCD19205617
• 分子量: 139.221
• InChiKey: MJZFHGILSSSGFK-UHFFFAOYSA-N

物化性质

• 沸点：
  250.8±20.0 °C(Predicted)
• 密度：
  1.084±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  9
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.142
• 拓扑面积：
  54.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(3-thienyl)allylamine 在 4-二甲氨基吡啶 、 N-溴代丁二酰亚胺(NBS) 、 2,2'-bis[di(3,5-di-tert-butyl-4-methoxyphenyl)phosphino]-1,1'-binaphthyl 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 26.0h， 生成 (R)-5-(bromomethyl)-2-(4-bromophenyl)-5-(thiophen-3-yl)-4,5-dihydrooxazole
  参考文献：
  名称：

  Enantioselective Bromocyclization of Allylic Amides Catalyzed by BINAP Derivatives

  摘要：

  A highly enantioselective bromocyclization of allylic amides with N-bromosuccinimide (NBS) was developed with DTBM-BINAP as a catalyst, affording chiral oxazolines with a tetrasubstituted carbon center in high yield with up to 99% ee. By utilizing the bromo substituent as a handle, the obtained compounds were converted to synthetically useful chiral building blocks.

  DOI：

  10.1021/acs.orglett.5b00220
• 作为产物：
  描述：

  3-乙酰基噻吩 在 吡啶 、 potassium hydrogensulfate 、 N-氯代丁二酰亚胺 、 二苯基二硒醚 、 一水合肼 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 2-(3-thienyl)allylamine
  参考文献：
  名称：

  不饱和杂环胺是多巴胺β-羟化酶的有效时间依赖性抑制剂。

  摘要：

  DOI：

  10.1021/jm00153a002

文献信息

• Renal-selective prodrugs for control of renal sympathetic nerve activity in the treatment of hypertension
  申请人：G.D. Searle & Co.

  公开号：US20030220521A1

  公开（公告）日：2003-11-27

  Renal-selective prodrugs are described which are preferentially converted in the kidney to compounds capable of inhibiting synthesis of catecholamine-type neurotransmitters involved in renal sympathetic nerve activity. The prodrugs described herein are derived from inhibitor compounds capable of inhibiting one or more of the enzymes involved in catecholamine synthesis, such compounds being classifiable as tyrosine hydroxylase inhibitors, or as dopa-decarboxylase inhibitors, or as dopamine-&bgr;-hydroxylase inhibitors. These inhibitor compounds are linked to a chemical moiety, such as a glutamic acid derivative, by a cleavable bond which is recognized selectively by enzymes located predominantly in the kidney. The liberated inhibitor compound is then available in the kidney to inhibit one or more of the enzymes involved in catecholamine synthesis. Inhibition of renal catecholamine synthesis can suppress heightened renal nerve activity associated with sodium-retention related disorders such as hypertension. Conjugates of particular interest are glutamyl derivatives of dopamine-&bgr;-hydroxylase inhibitors, of which N-acetyl-&ggr;-glutamyl fusaric acid hydrazide (shown below) is preferred. 1

  本文描述了一种肾选择性的前药，其在肾脏中优先转化为能够抑制参与肾交感神经活动的儿茶酚型神经递质合成的化合物。本文所描述的前药来源于能够抑制儿茶酚合成中的一个或多个酶的抑制剂化合物，这些化合物可分类为酪氨酸羟化酶抑制剂，多巴脱羧酶抑制剂或多巴胺-&bgr;-羟化酶抑制剂。这些抑制剂化合物通过可被肾脏中大量存在的酶选择性识别的可裂解键与化学基团（如谷氨酸衍生物）连接。释放的抑制剂化合物然后可在肾脏中用于抑制儿茶酚合成中的一个或多个酶。抑制肾脏儿茶酚合成可抑制与钠潴留相关的疾病（如高血压）相关的增强肾脏神经活动。特别感兴趣的共轭物是多巴胺-&bgr;-羟化酶抑制剂的谷氨酰衍生物，其中N-乙酰-&ggr;-谷氨酰富萨酸肼（如下图所示）是首选。1
• Renal-selective prodrugs for control of renal smpathetic nerve activity in the treatment of hypertension
  申请人：G.D. Searle & Co.

  公开号：US20040101523A1

  公开（公告）日：2004-05-27

  Renal-selective prodrugs are described which are preferentially converted in the kidney to compounds capable of inhibiting synthesis of catecholamine-type neurotransmitters involved in renal sympathetic nerve activity. The prodrugs described herein are derived from inhibitor compounds capable of inhibiting one or more of the enzymes involved in catecholamine synthesis, such compounds being classifiable as tyrosine hydroxylase inhibitors, or as dopa-decarboxylase inhibitors, or as dopamine-&bgr;-hydroxylase inhibitors. These inhibitor compounds are linked to a chemical moiety, such as a glutamic acid derivative, by a cleavable bond which is recognized selectively by enzymes located predominantly in the kidney. The liberated inhibitor compound is then available in the kidney to inhibit one or more of the enzymes involved in catecholamine synthesis. Inhibition of renal catecholamine synthesis can suppress heightened renal nerve activity associated with sodium-retention related disorders such as hypertension. Conjugates of particular interest are glutamyl derivatives of dopamine-&bgr;-hydroxylase inhibitors, of which N-acetyl-&ggr;-glutamyl fusaric acid hydrazide (shown below) is preferred. 1

  本文描述了肾脏选择性前药，这些前药被优先转化为能够抑制与肾脏交感神经活动相关的儿茶酚类神经递质合成的化合物。所述前药源自能够抑制儿茶酚类合成中涉及的一个或多个酶的抑制剂化合物，这些化合物可分类为酪氨酸羟化酶抑制剂，或多巴脱羧酶抑制剂，或是多巴胺-β-羟化酶抑制剂。这些抑制剂化合物与化学基团（例如谷氨酸衍生物）通过可被肾脏内的酶特异性识别的可切断键连接。被释放的抑制剂化合物随后可在肾脏中抑制一个或多个涉及儿茶酚类合成的酶。抑制肾脏儿茶酚类合成可以抑制与钠潴留相关的疾病（如高血压）所伴随的过度肾脏神经活动。特别感兴趣的结合物是多巴胺-β-羟化酶抑制剂的谷氨酰衍生物，其中N-乙酰-γ-谷氨酰菌核酸酸肼（如下图所示）是首选。1
• Novel allylic amines
  申请人：MERRELL DOW PHARMACEUTICALS INC.

  公开号：EP0187390A2

  公开（公告）日：1986-07-16

  57 This invention relates to novel β-methylene- thiophenethanamines which are mechanism-based inhibitors of dopamine beta-hydroxylase useful as antihypertensive agents.

  57 本发明涉及新型β-亚甲基噻吩乙胺，它是多巴胺β-羟化酶的机理抑制剂，可用作降压药。
• US4788301A
  申请人：——

  公开号：US4788301A

  公开（公告）日：1988-11-29
• [EN] RENAL-SELECTIVE PRODRUGS FOR THE TREATMENT OF HYPERTENSION
  申请人：G.D. SEARLE & CO.

  公开号：WO1991001724A1

  公开（公告）日：1991-02-21

  (EN) Renal-selective prodrugs are described which are preferentially converted in the kidney to compounds capable of inhibiting synthesis of catecholamine-type neurotransmitters involved in renal sympathetic nerve activity. The prodrugs described herein are derived from inhibitor compounds capable of inhibiting one or more of the enzymes involved in catecholamine synthesis, such compounds being classifiable as tyrosine hydroxylase inhibitors, or as depa-decarboxylase inhibitors, or as dopamine-$g(b)-hydroxylase inhibitors. These inhibitors compounds are linked to a chemical moiety, such as a glutamic acid derivative, by a cleavable bond which is recognized selectively by enzymes located predominantly in the kidney. The liberated inhibitor compound is then available in the kidney to inhibit one or more of the enzymes involved in catecholamine synthesis. Inhibition of renal catecholamine synthesis can suppress heightened renal nerve activity associated with sodium-retention related disorders such as hypertension. Conjugates of particular interest are glutamyl derivatives of dopamine-$g(b)-hydroxylase inhibitors, of which N-acetyl-Y-glutamyl fusaric acid is preferred.(FR) Sont décrits des promédicaments à sélectivité rénale qui sont préférentiellement transformés dans le rein en des composés capables d'inhiber la synthèse des neurotransmetteurs de type catécholamine impliqués dans l'activité rénale du nerf sympathique. Les promédicaments décrits ici sont dérivés de composés de l'inhibiteur capable d'inhiber un ou plusieurs enzymes impliqués dans la synthèse de la catécholamine, ces composés étant classifiables comme des inhibiteurs de tyrosine hydroxylase, ou comme des inhibiteurs de dépa-décarboxylase, ou comme des inhibiteurs de dopamine-$g(b)-hydroxylase. Ces composés d'inhibiteurs sont liés par une fraction de molécule chimique, comme un dérivé d'acide glutamique, par une liaison divisible qui est reconnue de manière sélective par des enzymes situés surtout sur le rein. Le composé d'inhibiteur libéré est alors disponible dans le rein pour inhiber un ou plusieurs des enzymes impliqués dans la synthèse de la catécholamine. L'inhibition de la synthèse rénale de la catécholamine peut supprimer l'activité rénale élevée du nerf associée aux désordres liés à la rétention de sodium tels que l'hypertension. Des conjugués d'un intérêt tout particulier sont les dérivés de glutamyle des inhibiteurs de dopamine-$g(b)-hydroxylase, et de préférence ceux d'acide fusarique N-acétyle-Y-glutamyle.