dithiocarbonic acid S-[1-cyclopentyl-2-(1-oxo-1λ4-[1,3]dithian-2-yl)ethyl] ester O-ethyl ester | 762243-65-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 硫杂环戊烷
• 英文名称: dithiocarbonic acid S-[1-cyclopentyl-2-(1-oxo-1λ4-[1,3]dithian-2-yl)ethyl] ester O-ethyl ester
• 英文别名: dithiocarbonic acid S-[1-cyclopentyl-2-(1-oxo-1λ⁴-[1,3]dithian-2-yl)ethyl] ester O-ethyl ester
• CAS: 762243-65-2
• 化学式: C₁₄H₂₄O₂S₄
• 分子量: 352.607
• InChiKey: ONEZXITZHAMSKO-UHFFFAOYSA-N

物化性质

• 沸点：
  552.3±43.0 °C(predicted)
• 密度：
  1.28±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  20.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  dithiocarbonic acid S-[1-cyclopentyl-2-(1-oxo-1λ4-[1,3]dithian-2-yl)ethyl] ester O-ethyl ester 在 三氟乙酸酐 、 sodium iodide 作用下， 以 丙酮 为溶剂， 以67%的产率得到dithiocarbonic acid S-(1-cyclopentyl-2-[1,3]dithian-2-ylethyl) ester O-ethyl ester
  参考文献：
  名称：

  Xanthates derived from 1,3-dithiane and its monosulfoxide; one-carbon radical equivalents

  摘要：

  The behaviour and synthetic scope of the C-2 centred radicals derived from 1,3-dithiane and 1,3-dithiane 1-oxide have been studied. Both radicals are available from the corresponding xanthates and have proved suitable substrates for the xanthate transfer reaction. However, the synthetic scope of the former is severely limited by the fact that it does not add to unactivated olefins. The latter on the other hand is a more promising radical precursor and undergoes smooth radical addition to a wide range of alkenes. Furthermore, subsequent transformations of some of the radical adducts confirm its utility as a synthetic equivalent of both the methyl and the formyl radical. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.06.061
• 作为产物：
  描述：

  dithiocarbonic acid S-[1,3]dithian-2-yl ester O-ethyl ester 在 过氧化双月桂酰 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 生成 dithiocarbonic acid S-[1-cyclopentyl-2-(1-oxo-1λ4-[1,3]dithian-2-yl)ethyl] ester O-ethyl ester
  参考文献：
  名称：

  Xanthates derived from 1,3-dithiane and its monosulfoxide; one-carbon radical equivalents

  摘要：

  The behaviour and synthetic scope of the C-2 centred radicals derived from 1,3-dithiane and 1,3-dithiane 1-oxide have been studied. Both radicals are available from the corresponding xanthates and have proved suitable substrates for the xanthate transfer reaction. However, the synthetic scope of the former is severely limited by the fact that it does not add to unactivated olefins. The latter on the other hand is a more promising radical precursor and undergoes smooth radical addition to a wide range of alkenes. Furthermore, subsequent transformations of some of the radical adducts confirm its utility as a synthetic equivalent of both the methyl and the formyl radical. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.06.061