<1R<1β(R^*,E,R^*),3aα,4β,7aβ>>-6-(Octahydro-4-hydroxy-7a-methyl-1H-inden-1-yl)-2,3-dimethyl-4-hepten-2-ol | 139238-88-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: <1R<1β(R^*,E,R^*),3aα,4β,7aβ>>-6-(Octahydro-4-hydroxy-7a-methyl-1H-inden-1-yl)-2,3-dimethyl-4-hepten-2-ol
• 英文别名: (1R,3aR,4S,7aR)-1-[(1R,2E,4R)-5-hydroxy-1,4,5-trimethylhex-2-enyl]-7a-methyloctahydro-1H-inden-4-ol；(1R,3aR,4S,7aR)-1-[(E,2R,5R)-6-hydroxy-5,6-dimethylhept-3-en-2-yl]-7a-methyl-1,2,3,3a,4,5,6,7-octahydroinden-4-ol
• CAS: 139238-88-3
• 化学式: C₁₉H₃₄O₂
• 分子量: 294.478
• InChiKey: QRAPIRXKHMRHBR-OHDCZZMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  <1R<1β(R^*,E,R^*),3aα,4β,7aβ>>-6-(Octahydro-4-hydroxy-7a-methyl-1H-inden-1-yl)-2,3-dimethyl-4-hepten-2-ol 在 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 以91%的产率得到<1R<1β(R^*,E,R),3aα,7aβ>>-6-(Octahydro-7a-methyl-1H-4-oxoinden-1-yl)-2,3-dimethyl-4-hepten-2-ol
  参考文献：
  名称：

  Two new approaches to the 25-hydroxy-vitamin D2 side chain

  摘要：

  Two approaches to the 25-hydroxy-vitamin D2 side chain have been developed based on the solvolysis of cyclopropylcarbinyl precursors. The first involves addition of trimethylcyclopropyllithium reagent 4 to a suitably protected C/D system 9. This reaction leads directly to cyclopropylcarbinols 10a,b which can be solvolyzed to the vitamin D2 side chain directly. The second approach uses an intermediate C/D system with a side chain allylic alcohol. Cyclopropanation of the allylic alcohol using Et2Zn/CH3CHI2 produces the same type of cyclopropylcarbinols 10a,b but in differing isomer ratios. Model studies and stereochemical differences in the two approaches are discussed.

  DOI：

  10.1021/jo00033a021
• 作为产物：
  描述：

  <1R-<1β,<αS*,βS*>,3aα,4aβ,7aβ>>-Octahydro-β,7a-dimethyl-4-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-α-(2',2'-dimethyl-1-ethenyl)-1H-indene-1-ethanol 在 氢氟酸 、 水 、 diethylzinc 、 对甲苯磺酸 作用下， 以 1,4-二氧六环 、 乙腈 为溶剂， 反应 2.5h， 生成 <1R<1β(R^*,E,R^*),3aα,4β,7aβ>>-6-(Octahydro-4-hydroxy-7a-methyl-1H-inden-1-yl)-2,3-dimethyl-4-hepten-2-ol
  参考文献：
  名称：

  Two new approaches to the 25-hydroxy-vitamin D2 side chain

  摘要：

  Two approaches to the 25-hydroxy-vitamin D2 side chain have been developed based on the solvolysis of cyclopropylcarbinyl precursors. The first involves addition of trimethylcyclopropyllithium reagent 4 to a suitably protected C/D system 9. This reaction leads directly to cyclopropylcarbinols 10a,b which can be solvolyzed to the vitamin D2 side chain directly. The second approach uses an intermediate C/D system with a side chain allylic alcohol. Cyclopropanation of the allylic alcohol using Et2Zn/CH3CHI2 produces the same type of cyclopropylcarbinols 10a,b but in differing isomer ratios. Model studies and stereochemical differences in the two approaches are discussed.

  DOI：

  10.1021/jo00033a021

文献信息

• VITAMIN D RECEPTOR ACTIVATORS AND METHODS OF MAKING
  申请人：Von Geldern Thomas W.

  公开号：US20090131379A1

  公开（公告）日：2009-05-21

  The invention relates to compounds that are vitamin D receptor activators, compositions comprising such compounds, methods of using such compounds and compositions, processes for preparing such compounds, and intermediates obtained during such processes.

  该发明涉及一种维生素D受体激活剂化合物，包括这种化合物的组合物，使用这种化合物和组合物的方法，制备这种化合物的过程，以及在这些过程中获得的中间体。
• Vitamin D receptor activators and methods of making
  申请人：Von Geldern Thomas W.

  公开号：US08377913B2

  公开（公告）日：2013-02-19

  The invention relates to compounds that are vitamin D receptor activators, compositions comprising such compounds, methods of using such compounds and compositions, processes for preparing such compounds, and intermediates obtained during such processes.

  本发明涉及一种维生素D受体激活剂化合物，包括该化合物的组合物、使用该化合物和组合物的方法、制备该化合物的方法以及在这些过程中获得的中间体。
• NEW VITAMIN D RECEPTOR ACTIVATORS AND METHODS OF MAKING
  申请人：Abbott Laboratories

  公开号：EP2222635A2

  公开（公告）日：2010-09-01
• US8377913B2
  申请人：——

  公开号：US8377913B2

  公开（公告）日：2013-02-19
• [EN] NEW VITAMIN D RECEPTOR ACTIVATORS AND METHODS OF MAKING<br/>[FR] NOUVEAUX ACTIVATEURS DU RÉCEPTEUR DE LA VITAMINE D ET PROCÉDÉS DE FABRICATION
  申请人：ABBOTT LAB

  公开号：WO2009067578A2

  公开（公告）日：2009-05-28

  The invention relates to compounds that are vitamin D receptor activators, compositions comprising such compounds, methods of using such compounds and compositions, processes for preparing such compounds, and intermediates obtained during such processes.