methyl 4-((5'R,8'S,11'S,13'S,14'S)-5'-hydroxy-13'-methyl-1',4',5',6',7',8',11',12',13',14',15',16'-dodecahydro-2'H-dispiro[[1,3]dioxolane-2,3'-cyclopenta[a]phenanthrene-17',2''-[1,3]dioxolan]-11'-yl)butanoate | 141304-45-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: methyl 4-((5'R,8'S,11'S,13'S,14'S)-5'-hydroxy-13'-methyl-1',4',5',6',7',8',11',12',13',14',15',16'-dodecahydro-2'H-dispiro[[1,3]dioxolane-2,3'-cyclopenta[a]phenanthrene-17',2''-[1,3]dioxolan]-11'-yl)butanoate
• CAS: 141304-45-2
• 化学式: C₂₇H₄₀O₇
• 分子量: 476.61
• InChiKey: BIFKEGVYBHAJSB-FKAWQAEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.87
• 重原子数：
  34.0
• 可旋转键数：
  4.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  83.45
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  methyl 4-((5'R,8'S,11'S,13'S,14'S)-5'-hydroxy-13'-methyl-1',4',5',6',7',8',11',12',13',14',15',16'-dodecahydro-2'H-dispiro[[1,3]dioxolane-2,3'-cyclopenta[a]phenanthrene-17',2''-[1,3]dioxolan]-11'-yl)butanoate 在 盐酸 、 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 3.5h， 生成 4-((8S,11S,13S,14S,17S)-17-Hydroxy-13-methyl-3-oxo-2,3,6,7,8,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-11-yl)-butyric acid methyl ester
  参考文献：
  名称：

  A sensitive enzyme-linked immunosorbent assay (ELISA) for testosterone: use of a novel heterologous hapten conjugated to penicillinase

  摘要：

  A microplate enzyme-linked immunosorbent assay (ELISA) has been developed for the measurement of testosterone in plasma. The assay uses a heterologous system consisting of a novel hapten 4-(17-beta-hydroxy-3-oxoestra-4,9-dien-11-beta-yl)butanoic acid (1) conjugated to penicillinase (beta-lactamase). The key reaction in the synthesis of the hapten was the cuprate-mediated 1,4-conjugate addition on 3,3,17,17-bis-ethylenedioxy-5-alpha,10-alpha-oxido-estr-9(11)-ene by the Grignard reagent derived from trimethyl 4-bro-moorthobutyrate; this regiospecifically introduces the 11-beta-butanoate function. The hapten-penicillinase conjugate was used in the assay in conjunction with the immunoglobulin G (IgG) fraction derived from a previously characterized, highly specific, antitestosterone serum raised against a testosterone-19-O-carboxymethyl ether-bovine serum albumin (T-19-O-CME-BSA) conjugate. This unique system represents one incorporating three elements of structural heterology: bridge, site, and ring heterology between the antigen hapten and enzyme-linked hapten. The limit of detection was 10 pg of testosterone with a sensitivity range between 15 and 1,000 pg. A low level of cross-reactivity with 5-alpha-dihydrotestosterone (6.17%) and 11-beta-hydroxytestosterone (1.03%) was noted. No interference was noted with other common androgens, estradiol, or progesterone. The sensitivity and selectivity observed in the assay may be attributable to the selection of penicillinase as the enzyme marker and the elements of conformational heterology between the antigen-linked and enzyme-conjugated steroid haptens.

  DOI：

  10.1016/0039-128x(92)90001-p
• 作为产物：
  描述：

  4-溴原丁酸三甲酯 、 Bed-epoxyestrene 在 magnesium 、 1,2-二溴乙烷 、 copper(l) chloride 作用下， 生成 辛二酸二甲酯 、 methyl 4-((5'R,8'S,11'S,13'S,14'S)-5'-hydroxy-13'-methyl-1',4',5',6',7',8',11',12',13',14',15',16'-dodecahydro-2'H-dispiro[[1,3]dioxolane-2,3'-cyclopenta[a]phenanthrene-17',2''-[1,3]dioxolan]-11'-yl)butanoate
  参考文献：
  名称：

  A sensitive enzyme-linked immunosorbent assay (ELISA) for testosterone: use of a novel heterologous hapten conjugated to penicillinase

  摘要：

  A microplate enzyme-linked immunosorbent assay (ELISA) has been developed for the measurement of testosterone in plasma. The assay uses a heterologous system consisting of a novel hapten 4-(17-beta-hydroxy-3-oxoestra-4,9-dien-11-beta-yl)butanoic acid (1) conjugated to penicillinase (beta-lactamase). The key reaction in the synthesis of the hapten was the cuprate-mediated 1,4-conjugate addition on 3,3,17,17-bis-ethylenedioxy-5-alpha,10-alpha-oxido-estr-9(11)-ene by the Grignard reagent derived from trimethyl 4-bro-moorthobutyrate; this regiospecifically introduces the 11-beta-butanoate function. The hapten-penicillinase conjugate was used in the assay in conjunction with the immunoglobulin G (IgG) fraction derived from a previously characterized, highly specific, antitestosterone serum raised against a testosterone-19-O-carboxymethyl ether-bovine serum albumin (T-19-O-CME-BSA) conjugate. This unique system represents one incorporating three elements of structural heterology: bridge, site, and ring heterology between the antigen hapten and enzyme-linked hapten. The limit of detection was 10 pg of testosterone with a sensitivity range between 15 and 1,000 pg. A low level of cross-reactivity with 5-alpha-dihydrotestosterone (6.17%) and 11-beta-hydroxytestosterone (1.03%) was noted. No interference was noted with other common androgens, estradiol, or progesterone. The sensitivity and selectivity observed in the assay may be attributable to the selection of penicillinase as the enzyme marker and the elements of conformational heterology between the antigen-linked and enzyme-conjugated steroid haptens.

  DOI：

  10.1016/0039-128x(92)90001-p