(3aS,5aR,9aR)-3a,4,5,5a,8,9-hexahydro-3-(4-hydroxy-4-methylpent-1-ynyl)-1H-cyclopenta[c]inden-6(7H)-one | 488124-19-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (3aS,5aR,9aR)-3a,4,5,5a,8,9-hexahydro-3-(4-hydroxy-4-methylpent-1-ynyl)-1H-cyclopenta[c]inden-6(7H)-one
• 英文别名: (3aS,5aR,9aS)-3-(4-hydroxy-4-methylpent-1-ynyl)-1,3a,4,5,5a,7,8,9-octahydrocyclopenta[i]inden-6-one
• CAS: 488124-19-2
• 化学式: C₁₈H₂₄O₂
• 分子量: 272.387
• InChiKey: ALMYSHSTQHISKX-VKJFTORMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (3aS,5aR,9aR)-3a,4,5,5a,8,9-hexahydro-3-(4-hydroxy-4-methylpent-1-ynyl)-1H-cyclopenta[c]inden-6(7H)-one 在 正丁基锂 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 9.0h， 生成 (1S,3R,5Z,7E)-20,21,22,22,23,23-hexahydro-18,21-cyclo-19,10-secocholesta-5,7,10(19)-triene-1,3,25-triol
  参考文献：
  名称：

  在 C(20) 处具有侧链锁定空间方向的骨化三醇 (1,25-二羟基维生素 D3) 的四环类似物的合成

  摘要：

  We present our first results on the synthesis of a new class of conformationally restricted vitamin D analogues bearing an extra five-membered ring formed by linking C(18) and C(2 1). Two analogues of calcitriol (1) with unsaturations at the extra ring and the lateral chain were prepared. The triene system was introduced by the convergent Wittig-Horner approach developed by Lythgoe [8] and F. Hoffmann-La Roche [9]. The key steps in the preparation of the requisite fragments were: i) the long-distance functionalization of ketal 11 at C(18) ii) the ring closure on 15 through an intramolecular aldol condensation to give the alpha,beta-unsaturated ketone 10, and iii) the Pd-catalyzed installation of the side chains.

  DOI：

  10.1002/1522-2675(200210)85:10<3251::aid-hlca3251>3.0.co;2-z
• 作为产物：
  描述：

  (3aS,5aR,6S,9aR)-6-{[(tert-butyl)(dimethyl)silyl]oxy}-3a,4,5,5a,6,7,8,9-octahydro-1H-cyclopenta[c]inden-3-yl trifluoromethanesulfonate 在 四氢吡咯 、 重铬酸吡啶 、 四(三苯基膦)钯 、 氢氟酸 、 4-甲基苯磺酸吡啶 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 7.5h， 生成 (3aS,5aR,9aR)-3a,4,5,5a,8,9-hexahydro-3-(4-hydroxy-4-methylpent-1-ynyl)-1H-cyclopenta[c]inden-6(7H)-one
  参考文献：
  名称：

  在 C(20) 处具有侧链锁定空间方向的骨化三醇 (1,25-二羟基维生素 D3) 的四环类似物的合成

  摘要：

  We present our first results on the synthesis of a new class of conformationally restricted vitamin D analogues bearing an extra five-membered ring formed by linking C(18) and C(2 1). Two analogues of calcitriol (1) with unsaturations at the extra ring and the lateral chain were prepared. The triene system was introduced by the convergent Wittig-Horner approach developed by Lythgoe [8] and F. Hoffmann-La Roche [9]. The key steps in the preparation of the requisite fragments were: i) the long-distance functionalization of ketal 11 at C(18) ii) the ring closure on 15 through an intramolecular aldol condensation to give the alpha,beta-unsaturated ketone 10, and iii) the Pd-catalyzed installation of the side chains.

  DOI：

  10.1002/1522-2675(200210)85:10<3251::aid-hlca3251>3.0.co;2-z

文献信息

• Synthesis of Tetracyclic Analogues of Calcitriol (1,25-Dihydroxyvitamin D3) with Side-Chain-Locked Spatial Orientations at C(20)
  作者：Carmen Varela、Kristina Nilsson、Mercedes Torneiro、Antonio Mouriño

  DOI：10.1002/1522-2675(200210)85:10<3251::aid-hlca3251>3.0.co;2-z

  日期：2002.10

  We present our first results on the synthesis of a new class of conformationally restricted vitamin D analogues bearing an extra five-membered ring formed by linking C(18) and C(2 1). Two analogues of calcitriol (1) with unsaturations at the extra ring and the lateral chain were prepared. The triene system was introduced by the convergent Wittig-Horner approach developed by Lythgoe [8] and F. Hoffmann-La Roche [9]. The key steps in the preparation of the requisite fragments were: i) the long-distance functionalization of ketal 11 at C(18) ii) the ring closure on 15 through an intramolecular aldol condensation to give the alpha,beta-unsaturated ketone 10, and iii) the Pd-catalyzed installation of the side chains.