Dithiocarbonic acid S-[2-(acetyl-phenyl-amino)-1-(1-oxo-1λ⁴-[1,3]dithian-2-ylmethyl)-ethyl] ester O-ethyl ester | 762243-71-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: Dithiocarbonic acid S-[2-(acetyl-phenyl-amino)-1-(1-oxo-1λ⁴-[1,3]dithian-2-ylmethyl)-ethyl] ester O-ethyl ester
• 英文别名: O-ethyl [1-(N-acetylanilino)-3-(1-oxo-1,3-dithian-2-yl)propan-2-yl]sulfanylmethanethioate
• CAS: 762243-71-0
• 化学式: C₁₈H₂₅NO₃S₄
• 分子量: 431.665
• InChiKey: FHIUBZGSXSCVIO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  26
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  149
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  Dithiocarbonic acid S-[2-(acetyl-phenyl-amino)-1-(1-oxo-1λ⁴-[1,3]dithian-2-ylmethyl)-ethyl] ester O-ethyl ester 在 过氧化双月桂酰 、 三氟乙酸酐 、 sodium iodide 、 碘甲烷 作用下， 以 二氯甲烷 、 水 、 1,2-二氯乙烷 、 丙酮 为溶剂， 反应 26.0h， 生成 (1-acetyl-2,3-dihydro-1H-indol-3-yl)acetaldehyde
  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-[2-(acetyl-phenyl-amino)-1-(1-oxo-1λ⁴-[1,3]dithian-2-ylmethyl)-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

文献信息

• Inexpensive Radical Methylation and Related Alkylations of Heteroarenes
  作者：Qi Huang、Samir Z. Zard

  DOI：10.1021/acs.orglett.8b00190

  日期：2018.3.2

  A simple method for the introduction of a methyl and higher aliphatic group to various heteroarenes using very inexpensive reagents is described. It is based on the radical addition of a carboxylic xanthate followed by decarboxylation. Depending on the heteroarene structure, the decarboxylation can be spontaneous or induced by heating in N,N-dimethylacetamide or N-methyl pyrrolidone in a microwave

  描述了一种使用非常便宜的试剂将甲基和高级脂肪族基团引入各种杂芳烃的简单方法。它基于羧酸黄原酸酯的自由基加成，然后进行脱羧。取决于杂芳烃结构，脱羧可以是自发的，或者可以通过在微波炉中的N，N-二甲基乙酰胺或N-甲基吡咯烷酮中加热来引发。