(R,4E,6E)-8-((1R,3aS,7aR,E)-4-(2-((3R,5R)-3,5-bis((tert-butyldimethylsilyl)oxy)cyclohexylidene)ethylidene)-7a-methyloctahydro-1H-inden-1-yl)-3-ethyl-5-methylnona-4,6-dien-3-ol | 1451188-50-3

• 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: (R,4E,6E)-8-((1R,3aS,7aR,E)-4-(2-((3R,5R)-3,5-bis((tert-butyldimethylsilyl)oxy)cyclohexylidene)ethylidene)-7a-methyloctahydro-1H-inden-1-yl)-3-ethyl-5-methylnona-4,6-dien-3-ol
• CAS: 1451188-50-3
• 化学式: C₄₂H₇₆O₃Si₂
• 分子量: 685.235
• InChiKey: VPVSYZLUCDPMMC-UIHGNEDXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.71
• 重原子数：
  47.0
• 可旋转键数：
  11.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  38.69
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (R,4E,6E)-8-((1R,3aS,7aR,E)-4-(2-((3R,5R)-3,5-bis((tert-butyldimethylsilyl)oxy)cyclohexylidene)ethylidene)-7a-methyloctahydro-1H-inden-1-yl)-3-ethyl-5-methylnona-4,6-dien-3-ol 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以0.64 g的产率得到(1R,3R,7E,22E,24E)-24a-homo-19-nor-9,10-secoergosta-5,7,22,24-tetraen-1,3,25-triol
  参考文献：
  名称：

  Synthesis and crystallographic study of 1,25-dihydroxyergocalciferol analogs

  摘要：

  The hybrid analogs of 1,25-dihydroxyergocalciferol (PRI-5201 and PRI-5202) were synthesized as potential anticancer agents using a convergent strategy. The analogs were designed by combining a 19-nor modification of the A-ring with the homologated and rigidified ergocalciferol-like side-chain of the previously obtained analogs PRI-1906 and PRI-1907. The strategy also allowed the novel efficient synthesis of 19-nor-1,25-dihydroxyergocalciferol (paricalcitol, PRI-5100) and its (24R)-diastereomer (PRI-5101). The single crystal X-ray structures of the 19-nor analogs (PRI-5100 and PRI-5101) were solved and refined. The A-ring of both analogs adopts exclusively chair beta-conformation in the solid state. The side-chain of these analogs is coplanar with the CD-ring plane, while it is perpendicular in 1,25-dihydroxycholecalciferol. Crown Copyright (C) 2013 Published by Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2013.06.001
• 作为产物：
  描述：

  (((1R,3R)-5-(2-iodoethylidene)cyclohexane-1,3-diyl)bis(oxy))bis(tert-butyldimethylsilane) 在 disodium hydrogenphosphate 、 sodium amalgam 、 正丁基锂 、 二异丙胺 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 正己烷 为溶剂， 反应 7.75h， 生成 (R,4E,6E)-8-((1R,3aS,7aR,E)-4-(2-((3R,5R)-3,5-bis((tert-butyldimethylsilyl)oxy)cyclohexylidene)ethylidene)-7a-methyloctahydro-1H-inden-1-yl)-3-ethyl-5-methylnona-4,6-dien-3-ol
  参考文献：
  名称：

  Synthesis and crystallographic study of 1,25-dihydroxyergocalciferol analogs

  摘要：

  The hybrid analogs of 1,25-dihydroxyergocalciferol (PRI-5201 and PRI-5202) were synthesized as potential anticancer agents using a convergent strategy. The analogs were designed by combining a 19-nor modification of the A-ring with the homologated and rigidified ergocalciferol-like side-chain of the previously obtained analogs PRI-1906 and PRI-1907. The strategy also allowed the novel efficient synthesis of 19-nor-1,25-dihydroxyergocalciferol (paricalcitol, PRI-5100) and its (24R)-diastereomer (PRI-5101). The single crystal X-ray structures of the 19-nor analogs (PRI-5100 and PRI-5101) were solved and refined. The A-ring of both analogs adopts exclusively chair beta-conformation in the solid state. The side-chain of these analogs is coplanar with the CD-ring plane, while it is perpendicular in 1,25-dihydroxycholecalciferol. Crown Copyright (C) 2013 Published by Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2013.06.001