(2-Methyl-4-sulfanylidenepyran-3-yl) 2-chloroacetate | 1043933-19-2

• 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-Methyl-4-sulfanylidenepyran-3-yl) 2-chloroacetate
• CAS: 1043933-19-2
• 化学式: C₈H₇ClO₃S
• 分子量: 218.661
• InChiKey: JMCADXWKCZQCDY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  67.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2-Methyl-4-sulfanylidenepyran-3-yl) 2-chloroacetate 在 sodium acetate 、 乙酸酐 、 三苯基膦 作用下， 反应 0.5h， 以1.3 mg的产率得到7-methyl-2H-furo[2,3-c]pyran-2-one
  参考文献：
  名称：

  Preparation of 2H-Furo[2,3-c]pyran-2-one Derivatives and Evaluation of Their Germination-Promoting Activity

  摘要：

  The butenolide, 3-methyl-2H-furo[2,3-c]pyran-2-one (1), has recently been identified as the germination stimulant present in smoke that promotes the germination of seeds from a wide range of plant species. In this paper, we describe the preparation of a number of analogues of 2 and compare their efficacy in promoting seed germination of three highly smoke-responsive plant species, Lactuca sativa L. cv. Grand Rapids (Asteraceae), Emmenanthe penduliflora Benth. (Hydrophyllaceae), and Solanum orbiculatum Poir. (Solanaceae). The results show that the methyl substituent at C-3 in 1 is important for germination-promoting activity while substitution at C-7 reduces activity. In contrast, bioactivity is mostly retained with analogues substituted at C-4 or C-5.

  DOI：

  10.1021/jf0633241
• 作为产物：
  描述：

  麦芽醇 在 tetraphosphorus decasulfide 、 碳酸氢钠 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 3.17h， 生成 (2-Methyl-4-sulfanylidenepyran-3-yl) 2-chloroacetate
  参考文献：
  名称：

  Preparation of 2H-Furo[2,3-c]pyran-2-one Derivatives and Evaluation of Their Germination-Promoting Activity

  摘要：

  The butenolide, 3-methyl-2H-furo[2,3-c]pyran-2-one (1), has recently been identified as the germination stimulant present in smoke that promotes the germination of seeds from a wide range of plant species. In this paper, we describe the preparation of a number of analogues of 2 and compare their efficacy in promoting seed germination of three highly smoke-responsive plant species, Lactuca sativa L. cv. Grand Rapids (Asteraceae), Emmenanthe penduliflora Benth. (Hydrophyllaceae), and Solanum orbiculatum Poir. (Solanaceae). The results show that the methyl substituent at C-3 in 1 is important for germination-promoting activity while substitution at C-7 reduces activity. In contrast, bioactivity is mostly retained with analogues substituted at C-4 or C-5.

  DOI：

  10.1021/jf0633241