5,5-dimethyl-5H-thieno<3,2-b>pyran | 129969-32-0

• 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: 5,5-dimethyl-5H-thieno<3,2-b>pyran
• 英文别名: 5,5-dimethyl-5H-thieno[3,2-b]pyran；5,5-dimethylthieno[3,2-b]pyran
• CAS: 129969-32-0
• 化学式: C₉H₁₀OS
• mdl: MFCD28362790
• 分子量: 166.244
• InChiKey: JIVGFTRLLYSYQT-UHFFFAOYSA-N

物化性质

• 沸点：
  236.8±29.0 °C(Predicted)
• 密度：
  1.119±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.333
• 拓扑面积：
  37.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5,5-dimethyl-5H-thieno<3,2-b>pyran 在 N-溴代丁二酰亚胺(NBS) 、 N,N-二甲基乙醇胺 、 水 、 sodium hydride 作用下， 以 二甲基亚砜 、 甲苯 为溶剂， 反应 60.0h， 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：

  5H-Thieno[3,2-b]pyran-5-one 以 四氢呋喃 、 甲基溴化镁 为溶剂， 生成 5,5-dimethyl-5H-thieno<3,2-b>pyran
  参考文献：
  名称：

  Thienopyran derivatives, their use for treating hypertension and asthma

  摘要：

  通式为##STR1## 的噻吩并吡喃衍生物，其中径向##STR2## 表示公式##STR3## 中的一个，R表示氢或基团--CN，--CHO，--CH.dbd.NOH，--CONH.sub.2或--COOR.sub.1，R.sub.1表示基团（C.sub.1-C.sub.4）-烷基，n表示整数3、4或5，并提供了它们的制备方法、药物制剂以及它们用于治疗可以通过激活膜K.sup.+通道治愈的疾病，如高血压和哮喘。

  公开号：

  US05077307A1

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。
• 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。
• Thiophene systems. 16. Interesting contrasts in electrocyclic reactions for thieno[3,2-b]- and -[2,3-b]pyrans with chromenes
  作者：Ignatius J. Turchi、Jeffery B. Press、James J. McNally、Mary Pat Bonner、Kirk L. Sorgi

  DOI：10.1021/jo00069a026

  日期：1993.8

  Thienopyrans 3, 4, and 5 were synthesized and found to have remarkable differences in stability. Systems 3 and 5 undergo electrocyclic ring-opening to 8 and 18, respectively. In acid milieu at room temperature, system 5 exists in an equilibrium with ring-opened thienopyranone 18. Ground state and activation parameters for the open and closed forms of thienopyrans 3 and 5 as well as the isosteric chromene 2 were calculated using the AM1 Hamiltonian. The Gibbs' free energy differences between the open and closed isomers in each system were found to be predictive of the observed equilibria. The mechanism for ring-opening in both thienopyran systems is proposed to be acid-catalyzed based on the calculated temperatures required for ring-opening as well as experimentally determined results.