(2Z)-(5R)-2-[5-(t-butyldimethylsilyl)oxy-2-methylenecyclohexylidene]ethanol | 272776-93-9

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: (2Z)-(5R)-2-[5-(t-butyldimethylsilyl)oxy-2-methylenecyclohexylidene]ethanol
• 英文别名: (2Z)-2-[(5R)-5-[tert-butyl(dimethyl)silyl]oxy-2-methylidenecyclohexylidene]ethanol
• CAS: 272776-93-9
• 化学式: C₁₅H₂₈O₂Si
• 分子量: 268.472
• InChiKey: ACGPHRQKCDCZAG-RNQWEJQRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.04
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2Z)-(5R)-2-[5-(t-butyldimethylsilyl)oxy-2-methylenecyclohexylidene]ethanol 在 N-氯代丁二酰亚胺 、 正丁基锂 、 二甲基硫 、 双氧水 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 氯仿 为溶剂， 反应 3.0h， 生成 (5Z,7E)-(3R,24R)-3,24,25-tri(t-butyldimethylsilyl)oxy-9,10-secocholesta-5,7,10⁽¹⁹⁾-triene
  参考文献：
  名称：

  Characterization of new conjugated metabolites in bile of rats administered 24,25-dihydroxyvitamin D3 and 25-hydroxyvitamin D3

  摘要：

  The characterization of new conjugated vitamin D metabolites in rat bile was performed using HPLC, liquid chromatography/tandem mass spectrometry combined derivatization, and GC-MS. After the administration of 24,25-dihydroxyvitamin D-3 to rats, 23,25-dihydroxy-24-oxovitamin D-3 23-glucuronide, 3-epi-24,25-dihydroxyvitamin D-3 24-glucuronide, and 24,25-dihydroxyvitamin D-3 3-sulfate were obtained as new biliary metabolites together with 24,25-dihydroxyvitamin D-3 3- and 24-glucuronides. The above metabolites, except 24,25-dihydroxyvitamin D-3 3-glucuronide, were obtained from rats dosed with 25-hydroxyvitamin D-3. 23,25-Dihydroxyvitamin D-3 23-glucuronide was also obtained from the bile of rats administered 25-hydroxyvitamin D-3 in addition to its 3-glucuronide, 25-glucuronide, and 3-sulfate. Thus, it was found that 24,25-dihydroxyvitamin D-3 and 25-hydroxyvitamin D-3 were directly conjugated as glucuronide and sulfate, whereas at the C-23 position, they were hydroxylated and then conjugated. Furthermore, we found that the C-3 epimerization acts as one of the important pathways in vitamin D metabolism. (C) 2000 Elsevier Science Inc. All rights reserved.

  DOI：

  10.1016/s0039-128x(00)00087-8
• 作为产物：
  描述：

  (5S)-5,6-epoxy-1-(4-methoxybenzyl)oxy-2-hexyne 在 咪唑 、 sodium tetrahydroborate 、 四(三苯基膦)钯 、 三乙胺 、 红铝 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 、 乙腈 为溶剂， 反应 18.51h， 生成 (2Z)-(5R)-2-[5-(t-butyldimethylsilyl)oxy-2-methylenecyclohexylidene]ethanol
  参考文献：
  名称：

  Characterization of new conjugated metabolites in bile of rats administered 24,25-dihydroxyvitamin D3 and 25-hydroxyvitamin D3

  摘要：

  The characterization of new conjugated vitamin D metabolites in rat bile was performed using HPLC, liquid chromatography/tandem mass spectrometry combined derivatization, and GC-MS. After the administration of 24,25-dihydroxyvitamin D-3 to rats, 23,25-dihydroxy-24-oxovitamin D-3 23-glucuronide, 3-epi-24,25-dihydroxyvitamin D-3 24-glucuronide, and 24,25-dihydroxyvitamin D-3 3-sulfate were obtained as new biliary metabolites together with 24,25-dihydroxyvitamin D-3 3- and 24-glucuronides. The above metabolites, except 24,25-dihydroxyvitamin D-3 3-glucuronide, were obtained from rats dosed with 25-hydroxyvitamin D-3. 23,25-Dihydroxyvitamin D-3 23-glucuronide was also obtained from the bile of rats administered 25-hydroxyvitamin D-3 in addition to its 3-glucuronide, 25-glucuronide, and 3-sulfate. Thus, it was found that 24,25-dihydroxyvitamin D-3 and 25-hydroxyvitamin D-3 were directly conjugated as glucuronide and sulfate, whereas at the C-23 position, they were hydroxylated and then conjugated. Furthermore, we found that the C-3 epimerization acts as one of the important pathways in vitamin D metabolism. (C) 2000 Elsevier Science Inc. All rights reserved.

  DOI：

  10.1016/s0039-128x(00)00087-8