5.6-Dihydro-5,5-dimethyl-7H-thieno[3,2-b]pyran-7-one | 129969-30-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩并吡喃类
• 英文名称: 5.6-Dihydro-5,5-dimethyl-7H-thieno[3,2-b]pyran-7-one
• 英文别名: 5,6-dihydro-5,5-dimethyl-7H-thieno<3,2-b>pyran-7-one；6,7-Dihydro-5,5-dimethyl-5H-thieno[3,2-b]pyran-7-one；5,6-dihydro-5,5-dimethylthieno[3,2-b]pyran-7-one；5,6-dihydro-5,5-dimethyl-7H-thieno [3,2-b]pyran-7-one；5,6-Dihydro-5,5-dimethyl-7H-thieno[3,2-b]pyran-7-one；5,5-dimethyl-5H,6H,7H-thieno[3,2-b]pyran-7-one；5,5-dimethyl-6H-thieno[3,2-b]pyran-7-one
• CAS: 129969-30-8
• 化学式: C₉H₁₀O₂S
• mdl: MFCD22064387
• 分子量: 182.243
• InChiKey: NGCQGLVSMGNFAB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.444
• 拓扑面积：
  54.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5.6-Dihydro-5,5-dimethyl-7H-thieno[3,2-b]pyran-7-one 在 sodium tetrahydroborate 、 N-溴代丁二酰亚胺(NBS) 、 lithium aluminium tetrahydride 、 N,N-二甲基乙醇胺 、 sodium azide 、 molecular sieve 、 水 、 sodium hydride 、 对甲苯磺酸 、 三乙胺 作用下， 以 乙醚 、 乙醇 、 二氯甲烷 、 二甲基亚砜 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 98.0h， 生成 ((S)-1-Phenyl-ethyl)-carbamic acid (6S,7S)-5,5-dimethyl-7-(2-oxo-piperidin-1-yl)-6,7-dihydro-5H-thieno[3,2-b]pyran-6-yl ester
  参考文献：
  名称：

  Thiophene systems. 14. Synthesis and antihypertensive activity of novel 7-(cyclic amido)-6-hydroxythieno[3,2-b]pyrans and related compounds as new potassium channel activators

  摘要：

  The synthesis and antihypertensive activity of novel 7-(cyclic amido)-6-hydroxy-5,5-di-methylthieno[3,2-b]pyrans and related compounds are described. The compounds were tested for oral antihypertensive activity in spontaneously hypertensive rats (SHR) and selected compounds were evaluated in vitro for increases in Rb-86 efflux in rabbit isolated mesenteric arteries. The effects on activity in SHR of lactam ring size, the presence of heteroatoms in the lactam ring, the relative stereochemistry at C-6 and C-7, and the substituents on the thiophene ring are examined. The best racemic compound in this series is 32, trans-5,6-dihydro-6-hydroxy-5,5-di-methyl-2-nitro-7-(2-oxopiperidin-1-yl)-5H-thieno[3,2-b]pyran, which is 10-fold more potent than cromakalim with an ED30 = 0.015 mg/kg in SHR. Compound 32 could be resolved and the antihypertensive activity determined to reside primarily in the (6S,7S)-(-)-enantiomer 41. Surprisingly, the elimination of water to give the enamides 50-52, thiophene isosteres of bimakalim, diminishes activity significantly.

  DOI：

  10.1021/jm00101a020
• 作为产物：
  描述：

  3-methoxy-2-(3-methyl-1-oxo-2-buten-1-yl)-thiophene 在 三氯化硼 、 对甲苯磺酸 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 19.5h， 生成 5.6-Dihydro-5,5-dimethyl-7H-thieno[3,2-b]pyran-7-one
  参考文献：
  名称：

  McNally, James J.; Sanfilippo, Pauline J.; Fitzpatrick, Louis, Journal of Heterocyclic Chemistry, 1992, vol. 29, # 1, p. 247 - 250

  摘要：

  DOI：

文献信息

• Substituted thienopyrans as antihypertensive agents
  申请人：Ortho Pharmaceutical Corporation

  公开号：US04992435A1

  公开（公告）日：1991-02-12

  Substituted thienopyrans and processes for preparing the thienopyrans are disclosed. The thienopyrans are useful as antihypertensive agents; antianginals are peripheral antivasoconstrictive agents.

  本发明涉及替代噻吩并制备噻吩并的方法。这些噻吩并可用作降压药物；抗心绞痛药物和外周抗血管收缩药物。
• Process for the preparation of enantiomerically pure thienopyran
  申请人：Ortho Pharmaceutical Corporation

  公开号：US05457212A1

  公开（公告）日：1995-10-10

  A process for the preparation of enantiomerically pure thienopyran derivatives of the formula ##STR1## is described. The thienopyran derivatives are relaxants of smooth muscle tone and as such are useful in vascular tissue for the treatment of hypertension disease, angina and other vascular disorders characterized by poor regional perfusion.

  描述了一种制备配体纯度噻吩吡喃衍生物的过程，其化学式为##STR1##。这些噻吩吡喃衍生物是平滑肌张力松弛剂，因此在血管组织中对治疗高血压疾病、心绞痛和其他因局部灌注不良而表现出的血管疾病中很有用。
• Potassium channel activators and their use
  申请人：Cambridge Bioclinical Limited

  公开号：US06342517B1

  公开（公告）日：2002-01-29

  Novel thienopyran compounds are disclosed, useful as anti-hypertensive agents and for asthma treatment. One group of the compounds has a heterocyclic ring spiro-connected at the 7-position of the thienopyran ring structure. Use of thienopyran compounds in hair growth modulation is described.

  揭示了一种新型噻吩并环化合物，可用作降压药物和治疗哮喘。其中一组化合物在噻吩并环结构的7位处与杂环环螺联接。描述了噻吩并环化合物在调节头发生长中的应用。
• Substituted thienopyrans
  申请人：Ortho Pharmaceutical Corporation

  公开号：US05030736A1

  公开（公告）日：1991-07-09

  Substituted thienopyrans and processes for preparing the thienopyrans are disclosed. The thienopyrans are useful as antihypertensive agents; antianginals are peripheral antivasoconstrictive agents.

  本发明揭示了替代噻吩并制备噻吩的过程。这些噻吩可用作降压剂；抗心绞痛和外周抗血管收缩剂。
• The process for the preparation of enantiomerically pure thienopyran derivative
  申请人：ORTHO PHARMACEUTICAL CORPORATION

  公开号：EP0493048A1

  公开（公告）日：1992-07-01

  A process for the preparation of enantiomerically pure thienopyran derivatives of the formula is described. The thienopyran derivatives are relaxants of smooth muscle tone and as such are useful in vascular tissue for the treatment of hypertension disease, angina and other vascular disorders characterized by poor regional perfusion.

  一种制备对映体纯的式噻吩并吡喃衍生物的工艺 的对映体纯噻喃衍生物的制备方法。噻喃衍生物是平滑肌张力的松弛剂，因此可用于血管组织，治疗高血压病、心绞痛和其他以区域灌注不良为特征的血管疾病。