1,3-dithiolan-2-ylideneacetic acid | 72629-81-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 乙烯基硫酯
• 英文名称: 1,3-dithiolan-2-ylideneacetic acid
• 英文别名: 2-(1,3-dithiolan-2-ylidene)acetic acid；[1,3]dithiolan-2-yliden-acetic acid；[1,3]Dithiolan-2-yliden-essigsaeure；2-(1,3-Dithiolan-2-ylidene)acetic acid
• CAS: 72629-81-3
• 化学式: C₅H₆O₂S₂
• 分子量: 162.233
• InChiKey: ZCAWPDWFEZGXJW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  87.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,3-dithiolan-2-ylideneacetic acid 、 1,3-diphenylpent-1-yn-3-ol 在 三氟化硼乙醚 作用下， 以 甲苯 为溶剂， 反应 0.5h， 以45%的产率得到3-(1,3-dithiolan-2-ylidene)-6-ethyl-4,6-diphenyl-3,6-dihydro-2H-pyran-2-one
  参考文献：
  名称：

  Regiospecific 6-Endo-Annulation of in Situ Generated 3,4-Dienamides/Acids: Synthesis of δ-Lactams and δ-Lactones

  摘要：

  A novel and efficient method for the construction of alpha-(1,3-dithiolan-2-ylidene) delta-lactam and delta-lactone rings has been developed. It involves the reglospecific 6-endo-annulation of in situ generated 2-(1,3-dithiolan-2-ylidene)-3,4-dienamides/acids from the dehydrative coupling of alpha-oxo ketene dithioacetals with tertiary propargyl alcohols promoted by BF3 center dot Et2O. A range of alpha-(1,3-dithiolan-2-ylidene) delta-lactams and delta-lactones are obtained in good to high yields. In addition, indenes are prepared by using alpha-acetyl ketene dithioacetal as the precursor.

  DOI：

  10.1021/ol4007772
• 作为产物：
  描述：

  [1,3]dithiolan-2-ylidene-malonic acid diethyl ester 在 氢氧化钾 作用下， 生成 1,3-dithiolan-2-ylideneacetic acid
  参考文献：
  名称：

  Sulfur-containing carboxylic acid esters

  摘要：

  公开号：

  US02493071A1

文献信息

• Chou, Shin-Shou; Taniguchi, Eiji; Eto, Morifusa, Agricultural and Biological Chemistry, 1980, vol. 44, # 9, p. 2169 - 2178
  作者：Chou, Shin-Shou、Taniguchi, Eiji、Eto, Morifusa

  DOI：——

  日期：——
• Regiospecific 6-<i>Endo</i>-Annulation of <i>in Situ </i>Generated 3,4-Dienamides/Acids: Synthesis of δ-Lactams and δ-Lactones
  作者：Ying Liu、Badru-Deen Barry、Haifeng Yu、Jianquan Liu、Peiqiu Liao、Xihe Bi

  DOI：10.1021/ol4007772

  日期：2013.6.7

  A novel and efficient method for the construction of alpha-(1,3-dithiolan-2-ylidene) delta-lactam and delta-lactone rings has been developed. It involves the reglospecific 6-endo-annulation of in situ generated 2-(1,3-dithiolan-2-ylidene)-3,4-dienamides/acids from the dehydrative coupling of alpha-oxo ketene dithioacetals with tertiary propargyl alcohols promoted by BF3 center dot Et2O. A range of alpha-(1,3-dithiolan-2-ylidene) delta-lactams and delta-lactones are obtained in good to high yields. In addition, indenes are prepared by using alpha-acetyl ketene dithioacetal as the precursor.
• Sulfur-containing carboxylic acid esters
  申请人：ILFORD LTD

  公开号：US02493071A1

  公开（公告）日：1950-01-03