4,5-dimethyl-2,3-dihydrothiophene S-oxide | 113380-05-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氢噻吩类
• 英文名称: 4,5-dimethyl-2,3-dihydrothiophene S-oxide
• 英文别名: 4,5-Dimethyl-2,3-dihydrothiophene 1-oxide
• CAS: 113380-05-5
• 化学式: C₆H₁₀OS
• 分子量: 130.211
• InChiKey: XOTBGIGSJAPRBP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  8
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  36.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1-溴-3-甲基戊烷-4-酮 在 sodium hydroxide 、 双氧水 作用下， 以 水 、 丙酮 为溶剂， 反应 80.0h， 生成 4,5-dimethyl-2,3-dihydrothiophene S-oxide
  参考文献：
  名称：

  Dye-sensitized photooxygenation of 2,3-dihydrothiophenes: formation of stable 1,2-dioxetanes from 4,5-dialkyl-substituted derivatives

  摘要：

  Singlet oxygen reacts with 4,5-dimethyl- (1a), 4-ethyl-5-methyl- (1b), and 4-isopropyl-5-methyl-2,3-dihydrothiophene (1c) to give 1,2-dioxetanes 2a-c in high yields (> 90%). 2a-c represent the first examples of sulfur-substituted dioxetanes that could be isolated. Less than 5% of allylic hydroperoxides 3a, 4a, and 3b, identified by their H-1 NMR spectra, and less than 5% of S-oxides 5a-c were formed in competing ene reactions and sulfoxide-producing steps, respectively. Due to its decreased rigidity, dioxetane 2a is less stable than its oxygen counterpart. Increased flexibility of dioxetanes derived from dihydrothiophenes and dihydrothiopyrans, as compared to those derived from dihydrofurans and dihydropyrans, causes dioxetanes 9 and 16, obtained from 4-carbomethoxy-5-methyl-2,3-dihydrothiophene (8) and 5,6-dimethyl-3,4-dihydro-2H-thiopyran (14), to cleave into dicarbonyl compounds readily at low temperatures. Sulfur-substituted allylic hydroperoxides are also less stable than their oxygen counterparts. Formation of the expected endocyclic allylic hydroperoxides 3a, 3b, and 10 is inferred from the appearance of their H2O2 elimination products, thiophenes 7a, 7b and 13, respectively.

  DOI：

  10.1021/jo00012a041

文献信息

• Pyrimidine Derivative Condensed with a Non-Aromatic Ring
  申请人：Yonetoku Yasuhiro

  公开号：US20080070896A1

  公开（公告）日：2008-03-20

  There are provided new pyrimidine derivatives condensed with a non-aromatic ring selected from dihydrothiophene, dihydrofuran, cycloalkane moiety, and the like or pharmaceutically acceptable salts thereof; and a pharmaceutical composition comprising said compound as an active ingredient. These compounds exhibit excellent promoting activity on insulin secretion and activity against hyperglycemia. Hence, the pharmaceutical compositions comprising such compounds as active ingredients, based on these actions, are useful for treating and/or preventing insulin-dependent diabetes (type 1 diabetes), non-insulin-dependent diabetes (type 2 diabetes), insulin-resistant diseases, obesity, and the like.

  提供了一些新的嘧啶衍生物，其与二氢噻吩、二氢呋喃、环烷基等非芳香环结构缩合，或其药学上可接受的盐缩合；以及一种含有该化合物作为活性成分的制药组合物。这些化合物表现出对胰岛素分泌的促进活性和对高血糖的活性。因此，基于这些作用，包含这些化合物作为活性成分的制药组合物可用于治疗和/或预防胰岛素依赖性糖尿病（1型糖尿病）、非胰岛素依赖性糖尿病（2型糖尿病）、胰岛素抵抗性疾病、肥胖症等。
• PYRIMIDINE DERIVATIVE CONDENSED WITH NON-AROMATIC RING
  申请人：Astellas Pharma Inc.

  公开号：EP1803710A1

  公开（公告）日：2007-07-04

  There are provided new pyrimidine derivatives condensed with a non-aromatic ring selected from dihydrothiophene, dihydrofuran, cycloalkane moiety, and the like or pharmaceutically acceptable salts thereof; and a pharmaceutical composition comprising said compound as an active ingredient. These compounds exhibit excellent promoting activity on insulin secretion and activity against hyperglycemia. Hence, the pharmaceutical compositions comprising such compounds as active ingredients, based on these actions, are useful for treating and/or preventing insulin-dependent diabetes (type 1 diabetes), non-insulin-dependent diabetes (type 2 diabetes), insulin-resistant diseases, obesity, and the like.

  提供了与选自二氢噻吩、二氢呋喃、环烷基等的非芳香环缩合的新嘧啶衍生物或其药学上可接受的盐；以及包含上述化合物作为活性成分的药物组合物。这些化合物对胰岛素分泌和高血糖具有良好的促进作用。因此，基于这些作用，包含此类化合物作为活性成分的药物组合物可用于治疗和/或预防胰岛素依赖型糖尿病（1 型糖尿病）、非胰岛素依赖型糖尿病（2 型糖尿病）、胰岛素抵抗性疾病、肥胖症等。
• 1,2-Dioxetanes derived from 4,5-dimethyl-2,3-dihydrofuran and 4,5-dimethyl-2,3-dihydrothiophene. Synthesis via photooxygenation, activation parameters, and excitation properties
  作者：Waldemar Adam、Axel G. Griesbeck、Klaus Gollnick、Karen Knutzen-Mies

  DOI：10.1021/jo00242a028

  日期：1988.4
• ADAM, WALDEMAR;GRIESBECK, AXEL G.;GOLLNICK, KLAUS;KNUTZEN-MIES, KAREN, J. ORG. CHEM., 53,(1988) N 7, 1492-1495
  作者：ADAM, WALDEMAR、GRIESBECK, AXEL G.、GOLLNICK, KLAUS、KNUTZEN-MIES, KAREN

  DOI：——

  日期：——
• SUBSTITUIERTE PIPERIDINO-DIHYDROTHIENOPYRIMIDINE
  申请人：Boehringer Ingelheim International GmbH

  公开号：EP2215092B1

  公开（公告）日：2012-01-25