(8S,9R,10S,13S,14S,16S,17R)-17-(1-ethoxyethoxy)-9-hydroxy-3-methoxy-10,13,16-trimethyl-2,7,8,11,12,14,15,16-octahydro-1H-cyclopenta[a]phenanthrene-17-carbonitrile | 135299-86-4

• 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: (8S,9R,10S,13S,14S,16S,17R)-17-(1-ethoxyethoxy)-9-hydroxy-3-methoxy-10,13,16-trimethyl-2,7,8,11,12,14,15,16-octahydro-1H-cyclopenta[a]phenanthrene-17-carbonitrile
• CAS: 135299-86-4
• 化学式: C₂₆H₃₉NO₄
• 分子量: 429.6
• InChiKey: AFDHZOPNBJEHEX-CBFJVWFGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  31
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  71.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (8S,9R,10S,13S,14S,16S,17R)-17-(1-ethoxyethoxy)-9-hydroxy-3-methoxy-10,13,16-trimethyl-2,7,8,11,12,14,15,16-octahydro-1H-cyclopenta[a]phenanthrene-17-carbonitrile 在 盐酸 、 异丙苯 、 溴 、 potassium hydrogencarbonate 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 25.0h， 生成 21-Bromo-9α,17α-dihydroxy-16β-methylpregn-4-ene-3,20-dione
  参考文献：
  名称：

  Synthesis of corticoids from 9.alpha.-hydroxyandrost-4-ene-3,17-dione

  摘要：

  The synthesis of 17-alpha,21-bis(acetyloxy)-16-beta-methylpregna-4,9(11)-diene-3,20-dione (24) from the sterol-derived 9-alpha-hydroxyandrost-4-ene-3,17-dione (1) has been completed. The key steps in the synthesis are 16-beta-methylation and conversion of the 17-ketone to 17-beta-cyanohydrin 11. Elaboration of 11 to 9-alpha-hydroxy-16-beta-methylpregn-4-ene-3,20-dione (15) followed by 21-acetoxylation and simultaneous introduction of 9,11-unsaturation and 17-alpha-acetoxylation gave 24.

  DOI：

  10.1021/jo00029a032
• 作为产物：
  描述：

  9α-hydroxy-3-methoxy-3,5-androstenedione-17-one 在 吡啶盐酸盐 、 溶剂黄146 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 18.0h， 生成 (8S,9R,10S,13S,14S,16S,17R)-17-(1-ethoxyethoxy)-9-hydroxy-3-methoxy-10,13,16-trimethyl-2,7,8,11,12,14,15,16-octahydro-1H-cyclopenta[a]phenanthrene-17-carbonitrile
  参考文献：
  名称：

  Synthesis of corticoids from 9.alpha.-hydroxyandrost-4-ene-3,17-dione

  摘要：

  The synthesis of 17-alpha,21-bis(acetyloxy)-16-beta-methylpregna-4,9(11)-diene-3,20-dione (24) from the sterol-derived 9-alpha-hydroxyandrost-4-ene-3,17-dione (1) has been completed. The key steps in the synthesis are 16-beta-methylation and conversion of the 17-ketone to 17-beta-cyanohydrin 11. Elaboration of 11 to 9-alpha-hydroxy-16-beta-methylpregn-4-ene-3,20-dione (15) followed by 21-acetoxylation and simultaneous introduction of 9,11-unsaturation and 17-alpha-acetoxylation gave 24.

  DOI：

  10.1021/jo00029a032

文献信息

• PROCESS FOR DEHYDRATING CORTICOSTEROID INTERMEDIATES
  申请人：SCHERING CORPORATION

  公开号：EP0502112A1

  公开（公告）日：1992-09-09
• [EN] PROCESS FOR DEHYDRATING CORTICOSTEROID INTERMEDIATES
  申请人：——

  公开号：WO1991008218A1

  公开（公告）日：1991-06-13

  [EN] A process for preparing oxazoline corticosteroid intermediates of formula (V) wherein R<1> represents hydrogene (H), loweralkyl, phenyl or phenylalkyl; R<4> represents H or loweralkyl, preferably methyl having either the alpha or beta stereochemistry; and R<9> represents hydrogen, fluoro, chloro or loweralkyl. The process comprises contacting a compound of formula (III) herein, with (A) Vilsmeier reagent, followed by acid hydrolysis to yield the compound of formula (V); or alternatively, (B) an acid having a pKa of less than 5, to yield the compound of formula (V).
  [FR] Procédé de préparation d'intermédiaires de corticostéroïdes d'oxazoline de la formule (V), dans laquelle R1 représente hydrogène (H), alkyle inférieur, phényle ou phénylalkyle; R4 représente H ou alkyl inférieur, de préférence méthyle ayant la stéréochimie soit alpha soit beta; et R9 représente hydrogène, fluoro, chloro ou alkyle inférieur. Le procédé consiste à mettre en contact un composé de la formule (III), avec (A) un réactif de Vilsmeier, suivi par l'hydrolyse d'acide afin de produire le composé de la formule (V); ou alternativement, (B) un acide ayant un pKa inférieur à 5, afin de produire le composé de la formule (V).