bis{4-[17-trimethylsilyloxy-1,3,5(10)-estratrien-3-yloxy]butyl} disulfide | 823214-56-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: bis{4-[17-trimethylsilyloxy-1,3,5(10)-estratrien-3-yloxy]butyl} disulfide
• CAS: 823214-56-8
• 化学式: C₅₀H₇₈O₄S₂Si₂
• 分子量: 863.47
• InChiKey: OFDTZHDXYQQUTP-UTCHONCBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  14.24
• 重原子数：
  58.0
• 可旋转键数：
  17.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  36.92
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  bis{4-[17-trimethylsilyloxy-1,3,5(10)-estratrien-3-yloxy]butyl} disulfide 在 四(三苯基膦)钯 、 4-苯基脲唑 、 ammonium chloride 、 sodium 4-methylbenzenesulfinate 、 三苯基膦 、 柠檬酸 、 锌 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 25.0h， 生成
  参考文献：
  名称：

  Design and synthesis of an aminobenzo-15-crown-5-labeled estradiol tethered with disulfide linkage

  摘要：

  A novel measuring method (electroimmunoassay) of 17beta-estradiol (E,) in urine or blood was proposed on the basis of a competition between E-2 and a labeled E-2 against an immobilizing antibody. To evaluate the principle, 3-{4-[17beta-hydroxy-1,3,5(10)-estratrien-3-yloxy]butyldisulfanyl}-N-(6,7,9,10,12,13,15,16-octahydro-5,8,11,14,17-pentaoxabenzocyclopentadecen-2-yl) succinamic acid (1) was designed and synthesized as a novel aminobenzo-15-crown-5-containing E-2 tethered with disultide linkage. Two thiol-intermediates 5b and 19c were efficiently synthesized from mercaptosuccinic acid 7 and 4,4-dithiodibutyric acid 12, respectively. Formations of disulfide linkages from less reactive thiols were examined and 4-phenyl-1,2,4-triazoline-3,5-dione (PTAD) could be employed for the formation of an unsymmetrical disulfide 20c from 5b and 19c. Then, removal of TMS- and allyl-protecting groups in 20c successfully afforded the crown ether-containing E-2 1. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.09.109
• 作为产物：
  描述：

  1-Bromo-4-(4-bromo-butyldisulfanyl)-butane 在 potassium carbonate 、 三乙胺 作用下， 以 四氢呋喃 、 丙酮 为溶剂， 反应 40.0h， 生成 bis{4-[17-trimethylsilyloxy-1,3,5(10)-estratrien-3-yloxy]butyl} disulfide
  参考文献：
  名称：

  Design and synthesis of an aminobenzo-15-crown-5-labeled estradiol tethered with disulfide linkage

  摘要：

  A novel measuring method (electroimmunoassay) of 17beta-estradiol (E,) in urine or blood was proposed on the basis of a competition between E-2 and a labeled E-2 against an immobilizing antibody. To evaluate the principle, 3-{4-[17beta-hydroxy-1,3,5(10)-estratrien-3-yloxy]butyldisulfanyl}-N-(6,7,9,10,12,13,15,16-octahydro-5,8,11,14,17-pentaoxabenzocyclopentadecen-2-yl) succinamic acid (1) was designed and synthesized as a novel aminobenzo-15-crown-5-containing E-2 tethered with disultide linkage. Two thiol-intermediates 5b and 19c were efficiently synthesized from mercaptosuccinic acid 7 and 4,4-dithiodibutyric acid 12, respectively. Formations of disulfide linkages from less reactive thiols were examined and 4-phenyl-1,2,4-triazoline-3,5-dione (PTAD) could be employed for the formation of an unsymmetrical disulfide 20c from 5b and 19c. Then, removal of TMS- and allyl-protecting groups in 20c successfully afforded the crown ether-containing E-2 1. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.09.109