3-Mercapto-N-(6,7,9,10,12,13,15,16-octahydro-5,8,11,14,17-pentaoxa-benzocyclopentadecen-2-yl)-succinamic acid allyl ester | 823214-52-4

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 3-Mercapto-N-(6,7,9,10,12,13,15,16-octahydro-5,8,11,14,17-pentaoxa-benzocyclopentadecen-2-yl)-succinamic acid allyl ester
• 英文别名: Prop-2-enyl 4-oxo-4-(2,5,8,11,14-pentaoxabicyclo[13.4.0]nonadeca-1(15),16,18-trien-17-ylamino)-3-sulfanylbutanoate；prop-2-enyl 4-oxo-4-(2,5,8,11,14-pentaoxabicyclo[13.4.0]nonadeca-1(15),16,18-trien-17-ylamino)-3-sulfanylbutanoate
• CAS: 823214-52-4
• 化学式: C₂₁H₂₉NO₈S
• 分子量: 455.529
• InChiKey: SYAZNUCBEMFZMW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  31
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  103
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  3-Mercapto-N-(6,7,9,10,12,13,15,16-octahydro-5,8,11,14,17-pentaoxa-benzocyclopentadecen-2-yl)-succinamic acid allyl ester 在 四(三苯基膦)钯 、 4-苯基脲唑 、 sodium 4-methylbenzenesulfinate 、 三苯基膦 、 柠檬酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 21.0h， 生成 3-[4-[[(8R,9S,13S,14S,17S)-17-hydroxy-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-3-yl]oxy]butyldisulfanyl]-4-oxo-4-(2,5,8,11,14-pentaoxabicyclo[13.4.0]nonadeca-1(15),16,18-trien-17-ylamino)butanoic acid
  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：

  3-[2-Carboxy-1-(6,7,9,10,12,13,15,16-octahydro-5,8,11,14,17-pentaoxa-benzocyclopentadecen-2-ylcarbamoyl)-ethyldisulfanyl]-N-(6,7,9,10,12,13,15,16-octahydro-5,8,11,14,17-pentaoxa-benzocyclopentadecen-2-yl)-succinamic acid 在 ammonium chloride 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 锌 作用下， 以 四氢呋喃 为溶剂， 反应 27.0h， 生成 3-Mercapto-N-(6,7,9,10,12,13,15,16-octahydro-5,8,11,14,17-pentaoxa-benzocyclopentadecen-2-yl)-succinamic acid allyl ester
  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

文献信息

• Design and synthesis of an aminobenzo-15-crown-5-labeled estradiol tethered with disulfide linkage
  作者：Shinya Harusawa、Kazufumi Yoshida、Chihiro Kojima、Lisa Araki、Takushi Kurihara

  DOI：10.1016/j.tet.2004.09.109

  日期：2004.12

  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.