Methyl 3-hydroxy-3-thiophen-2-ylhex-5-enedithioate | 1454846-27-5

• 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: Methyl 3-hydroxy-3-thiophen-2-ylhex-5-enedithioate
• CAS: 1454846-27-5
• 化学式: C₁₁H₁₄OS₃
• 分子量: 258.43
• InChiKey: SGDUBLXUIOGFTR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  106
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Methyl 3-hydroxy-3-thiophen-2-ylhex-5-enedithioate 在 yttrium(III) trifluoromethanesulfonate 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 12.0h， 以93%的产率得到3-thiophen-2-ylhexa-3,5-dienedithioic acid methyl ester
  参考文献：
  名称：

  Regioselective dehydrative intramolecular heteroannulation of β-allyl-β-hydroxy dithioesters: facile and straightforward entry to 2H-thiopyrans

  摘要：

  beta-Allyl-beta-hydroxy dithioesters have been employed in the synthesis of hitherto unreported and synthetically demanding 2H-thiopyrans via regioselective intramolecular annulation strategy. Lewis acid BF3 center dot Et2O efficiently mediates the regioselective dehydration followed by intramolecular thioannulation at room temperature. The attractive features of this protocol include mild conditions, high atom-economy and excellent yields with the elimination of water as the only by-product. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.12.020
• 作为产物：
  描述：

  3-oxo-3-thiophen-2-yl-dithiopropionic acid methyl ester 、 烯丙基溴化镁 以 四氢呋喃 、 乙醚 为溶剂， 生成 Methyl 3-hydroxy-3-thiophen-2-ylhex-5-enedithioate
  参考文献：
  名称：

  Regioselective dehydrative intramolecular heteroannulation of β-allyl-β-hydroxy dithioesters: facile and straightforward entry to 2H-thiopyrans

  摘要：

  beta-Allyl-beta-hydroxy dithioesters have been employed in the synthesis of hitherto unreported and synthetically demanding 2H-thiopyrans via regioselective intramolecular annulation strategy. Lewis acid BF3 center dot Et2O efficiently mediates the regioselective dehydration followed by intramolecular thioannulation at room temperature. The attractive features of this protocol include mild conditions, high atom-economy and excellent yields with the elimination of water as the only by-product. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.12.020

文献信息

• Y(OTf)3 catalyzed substitution dependent oxidative C(sp3)–C(sp3) cleavage and regioselective dehydration of β-allyl-β-hydroxydithioesters: alternate route to α,β-unsaturated ketones and functionalized dienes
  作者：Sushobhan Chowdhury、Tanmoy Chanda、Ganesh Chandra Nandi、Suvajit Koley、B. Janaki Ramulu、S.K. Pandey、Maya Shankar Singh

  DOI：10.1016/j.tet.2013.07.092

  日期：2013.10

  beta-Allyl-beta-hydroxydithioesters have been generated by the regioselective Grignard addition to the beta-oxodithioesters. They have been successfully employed in selective C(sp(3))-C(sp(3)) bond cleavage to construct alpha,beta-unsaturated ketone residues by the treatment of an emerging catalyst yttrium(III)triflate for the first time. On the other hand, hetaryl substituted beta-allyl-beta-hydroxydithioesters led to the useful diene precursors through selective dehydration under the similar conditions. (c) 2013 Elsevier Ltd. All rights reserved.