(3aR,4S,7aS)-(Z)-1-ethylidene-7a-methyloctahydro-1H-4-indenol | 93489-58-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3aR,4S,7aS)-(Z)-1-ethylidene-7a-methyloctahydro-1H-4-indenol
• 英文别名: (Z,3aR,4S,7aS)-1-ethylidene-octahydro-7a-methyl-1H-indene-4-ol；(1Z,3aR,4S,7aS)-1-ethylidene-7a-methyloctahydro-1H-inden-4-ol；(1Z,3aR,4S,7aS)-1-ethylidene-7a-methyl-3,3a,4,5,6,7-hexahydro-2H-inden-4-ol
• CAS: 93489-58-8
• 化学式: C₁₂H₂₀O
• 分子量: 180.29
• InChiKey: WXRWVZJUUDRYFG-BQUAOGAQSA-N

物化性质

• 沸点：
  262.5±19.0 °C(Predicted)
• 密度：
  1.062±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (3aR,4S,7aS)-(Z)-1-ethylidene-7a-methyloctahydro-1H-4-indenol 在 2,6-二甲基吡啶 、 4-二甲氨基吡啶 、 二甲基氯化铝 作用下， 以 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 32.0h， 生成 (R)-3-((3aR,4S,7aS)-7a-Methyl-4-triethylsilanyloxy-3a,4,5,6,7,7a-hexahydro-3H-inden-1-yl)-butyronitrile
  参考文献：
  名称：

  Noncalcemic, Antiproliferative, Transcriptionally Active, 24-Fluorinated Hybrid Analogues of the Hormone 1α,25-Dihydroxyvitamin D₃. Synthesis and Preliminary Biological Evaluation

  摘要：

  Four new hybrid analogues of 1 alpha,25-dihydroxyvitamin D-3 (1) have been synthesized in a convergent manner by joining A-ring and C,D-ring fragments. Each hybrid analogue, having a noncalcemic 1-hydroxymethyl group and a potentiating 16-ene 24,24-difluorinated C,D-ring side chain, was designed to be lipophilic and inert toward 24-hydroxylase enzyme catabolism. Each hybrid analogue with 1 beta,3 alpha-substituent stereochemistry (i.e., analogues 3b and 4b) showed a pharmacologically desirable combination of in vitro high antiproliferative activity in two different cell lines and high transcriptional activity with also low calcemic activity in vivo.

  DOI：

  10.1021/jm980031t
• 作为产物：
  描述：

  (3aR,4S,7aS)-4-bromo-7a-methyloctahydro-1H-indene-1,5-dione 在 六甲基磷酰三胺 、 lithium aluminium tetrahydride 、 重铬酸吡啶 、 potassium tert-butylate 、 potassium hydride 、 lithium tri-t-butoxyaluminum hydride 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 51.92h， 生成 (3aR,4S,7aS)-(Z)-1-ethylidene-7a-methyloctahydro-1H-4-indenol
  参考文献：
  名称：

  A simple way to (3aR,4S,7aS)-(Z)-ethylideneoctahydro-7a-methyl-1H-4-indenol, a synthon for total synthesis of vitamins D

  摘要：

  DOI：

  10.1021/jo00258a025

文献信息

• Stereoselective total synthesis of 1α,25S,26-trihydroxycholecalciferol
  作者：P.M. Wovkulich、F. Barcelos、A.D. Batcho、J.F. Sereno、E.G. Baggiolini、B.M. Hennessy、M.R. UskokoviĆ

  DOI：10.1016/0040-4020(84)80011-3

  日期：1984.1

  A total synthesis of 1α,25S,26-trihydroxycholecalciferol (2) has been accomplished via an efficient convergent approach. The remote chiral center at C-25 was introduced by a regiospecific and diastereoselective 1,3-dipolar cycloaddition of the C-23 nitrone 27 with methyl methacrylate. Subsequent transformation of the resulting isoxazolidine led to the key synthon 3, which on coupling to the anion 4

  1α，25S，26-trihydroxycholecalciferol（2）的总合成已通过一种有效的收敛方法完成。C-25的远程手性中心是通过C-23硝酮27与甲基丙烯酸甲酯的区域专一性和非对映选择性1,3-偶极环加成反应引入的。所得异恶唑烷的后续转化导致关键合成子3，该合成子与阴离子4偶联并脱保护后生成代谢物2。
• 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。
• Process for producing vitamin D derivative using convergent method
  申请人：Chugai Seiyaku Kabushiki Kaisha

  公开号：US08173824B2

  公开（公告）日：2012-05-08

  There are provided a novel process for producing [(5Z,7E)-(1S,3R,20S)-1,3-dihydroxy-9,10-secopregna-5,7,10(19),16-tetraen-20-yl}oxy]-N-(2,2,3,3,3-pentafluoropropyl)acetamide, which process is shown in the following reaction scheme: an intermediate useful for carrying out the process, and a process for producing the intermediate.

  提供了一种新的生产[(5Z,7E)-(1S,3R,20S)-1,3-二羟基-9,10-去氢孕酮-5,7,10(19),16-四烯-20-基}氧基]-N-(2,2,3,3,3-五氟丙基)乙酰胺的方法，该方法如下反应方案所示：一种用于实施该方法的中间体，以及生产该中间体的方法。
• Antiproliferative vitamin D.sub.3 hybrids
  申请人：The Johns Hopkins University

  公开号：US05830885A1

  公开（公告）日：1998-11-03

  Vitamin D.sub.3 analogues of formula ##STR1## wherein R represents a 1-hydroxyalkyl group or 1-fluoroalkyl group in a trans- configuration with a 3-hydroxyl group on the A ring and R.sup.2 represents the substituents completing a vitamin D.sub.3 analogue. These novel compounds are potent anti-proliferative substances with activities comparable to that of calcitriol but with vitamin D.sub.3 receptor binding ratings of less than 10.sup.-3 compared to that of calcitriol.

  维生素D.sub.3类似物的化学式为##STR1##其中R代表1-羟基烷基或1-氟烷基，以反式构型与A环上的3-羟基基团相连，R.sup.2代表完成维生素D.sub.3类似物的取代基。这些新化合物是具有强效抗增殖作用的物质，其活性可与钙三醇相媲美，但其与维生素D.sub.3受体的结合评级低于10.sup.-3，相比之下，钙三醇的评级要高。
• PROCESS FOR PRODUCING VITAMIN D DERIVATIVE USING CONVERGENT METHOD
  申请人：Ogasawara Kunio

  公开号：US20100217020A1

  公开（公告）日：2010-08-26

  There are provided a novel process for producing [(5Z,7E)-(1S,3R,20S)-1,3-dihydroxy-9,10-secopregna-5,7,10(19),16-tetraen-20-yl}oxy]-N-(2,2,3,3,3-pentafluoropropyl)acetamide, which process is shown in the following reaction scheme: an intermediate useful for carrying out the process, and a process for producing the intermediate.

  提供了一种新的生产过程，用于生产[(5Z,7E)-(1S,3R,20S)-1,3-二羟基-9,10-secopregna-5,7,10(19),16-四烯-20-基}氧基]-N-(2,2,3,3,3-五氟丙基)乙酰胺，该过程如下反应方程所示：生产该中间体的有用方法和生产该中间体的过程。