(E)-S-phenyl 8-(tetrahydro-2H-pyran-2-yloxy)oct-2-en-6-ynethioate | 911826-91-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯硫酚酯
• 英文名称: (E)-S-phenyl 8-(tetrahydro-2H-pyran-2-yloxy)oct-2-en-6-ynethioate
• 英文别名: S-phenyl (E)-8-(oxan-2-yloxy)oct-2-en-6-ynethioate
• CAS: 911826-91-0
• 化学式: C₁₉H₂₂O₃S
• 分子量: 330.448
• InChiKey: LAZKWXDARPODTF-NTUHNPAUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  60.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (E)-S-phenyl 8-(tetrahydro-2H-pyran-2-yloxy)oct-2-en-6-ynethioate 在 硫化氢 、 二甲基二环氧乙烷 、 三乙胺 、 potassium hexacyanoferrate(III) 作用下， 以 1,4-二氧六环 、 水 、 丙酮 为溶剂， 反应 20.0h， 生成 1-Oxo-5-[5-(tetrahydro-pyran-2-yloxy)-pent-3-ynyl]-1λ⁴-[1,2]dithiolan-3-one
  参考文献：
  名称：

  Synthesis and Cytotoxicity of Leinamycin Antibiotic Analogues

  摘要：

  A simple synthesis of 1,2-dithiolan-3-ones from alpha,beta-unsaturated thiophenyl esters is reported. Introduction of the biologically active 1,2-dithiolan-3-one-1-oxide moiety of leinamycin into aldehydo-D-arabinose 11, the uridine derivative 16, and the deoxythymidine 21 was established. An extended bioactive part of leinamycin carrying a carbon-carbon triple bond was also synthesized. All of these analogues of leinamycin showed cytotoxic activity against HeLa3 tumor cells. Interestingly, the lipophilic, silyl group-containing derivatives proved to be more active than the hydrophilic counterparts.

  DOI：

  10.1021/jm060471h
• 作为产物：
  描述：

  Trimethyl-[(E)-6-(tetrahydro-pyran-2-yloxy)-hex-1-en-4-ynyloxy]-silane 在 碳酸氢钠 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 正己烷 为溶剂， 反应 16.0h， 生成 (E)-S-phenyl 8-(tetrahydro-2H-pyran-2-yloxy)oct-2-en-6-ynethioate
  参考文献：
  名称：

  Synthesis and Cytotoxicity of Leinamycin Antibiotic Analogues

  摘要：

  A simple synthesis of 1,2-dithiolan-3-ones from alpha,beta-unsaturated thiophenyl esters is reported. Introduction of the biologically active 1,2-dithiolan-3-one-1-oxide moiety of leinamycin into aldehydo-D-arabinose 11, the uridine derivative 16, and the deoxythymidine 21 was established. An extended bioactive part of leinamycin carrying a carbon-carbon triple bond was also synthesized. All of these analogues of leinamycin showed cytotoxic activity against HeLa3 tumor cells. Interestingly, the lipophilic, silyl group-containing derivatives proved to be more active than the hydrophilic counterparts.

  DOI：

  10.1021/jm060471h

文献信息

• Synthesis and Cytotoxicity of Leinamycin Antibiotic Analogues
  作者：Ákos Szilágyi、Ferenc Fenyvesi、Orsolya Majercsik、István F. Pelyvás、Ildikó Bácskay、Pálma Fehér、Judit Váradi、Miklós Vecsernyés、Pál Herczegh

  DOI：10.1021/jm060471h

  日期：2006.9.1

  A simple synthesis of 1,2-dithiolan-3-ones from alpha,beta-unsaturated thiophenyl esters is reported. Introduction of the biologically active 1,2-dithiolan-3-one-1-oxide moiety of leinamycin into aldehydo-D-arabinose 11, the uridine derivative 16, and the deoxythymidine 21 was established. An extended bioactive part of leinamycin carrying a carbon-carbon triple bond was also synthesized. All of these analogues of leinamycin showed cytotoxic activity against HeLa3 tumor cells. Interestingly, the lipophilic, silyl group-containing derivatives proved to be more active than the hydrophilic counterparts.