2beta,3beta,14alpha-三羟基-5beta-胆甾-7-烯-6-酮 | 7698-69-3

• 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
• 中文名称: 2beta,3beta,14alpha-三羟基-5beta-胆甾-7-烯-6-酮
• 英文名称: 22,25-Dideoxyecdysone
• 英文别名: 2β.3β.14α-Trihydroxy-5β-cholesten-(7)-on-(6)；2β,3β,14-Trihydroxy-5β,14α-cholesten-7-on-6；2β,3β,14α-Trihydroxy-5β-cholest-7-en-6-on；Cholest-7-en-6-one, 2,3,14-trihydroxy-, (2beta,3beta,5beta)-；(2S,3R,5R,9R,10R,13R,14S,17R)-2,3,14-trihydroxy-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-6-one
• CAS: 7698-69-3
• 化学式: C₂₇H₄₄O₄
• 分子量: 432.644
• InChiKey: QPGHAYOKHPQLQO-DXCOFLLLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  31
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  77.8
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2beta,3beta,14alpha-三羟基-5beta-胆甾-7-烯-6-酮 在 吡啶 、 三氟乙酸酐 作用下， 生成
  参考文献：
  名称：

  Synthesis of analogs of α-ecdysone. A simplified synthesis of 2β,3β,14α-trihydroxy-7-en-6-one-5β-steroids

  摘要：

  DOI：

  10.1016/s0039-128x(70)80099-x
• 作为产物：
  描述：

  5α-cholest-2,7-dien-6-one 在 盐酸 、 selenium(IV) oxide 、 碘 、 silver(I) acetate 作用下， 以 1,4-二氧六环 、 乙醇 为溶剂， 生成 2beta,3beta,14alpha-三羟基-5beta-胆甾-7-烯-6-酮
  参考文献：
  名称：

  Zur Synthese des Ecdysons. III. Mitteilung über Insektenhormone. Synthesen von 2β, 3β, 14α-Trihydroxy-6-keto-Δ⁷-A|B-cis-Steroiden

  摘要：

  AbstractThe synthesis of the tetracyclic skeleton of ecdysone with correct stereochemistry and substitution is described. 22,25‐Didehydroxy‐ecdysone and methyl (20S)‐2β,3β‐dihydroxy‐6‐oxo‐5β‐pregn‐7‐ene‐20‐carboxylate have been prepared. The latter is a key intermediate in the synthesis of ecdysone.

  DOI：

  10.1002/hlca.19660490518

文献信息

• Synthesis of Ecdysone. III. A Novel Synthesis of 14α-Hydroxy-7-en-6-oxo Steroids
  作者：HIROMU MORI、KENYU SHIBATA、KIYOSHI TSUNEDA、MASANOBU SAWAI

  DOI：10.1248/cpb.16.1593

  日期：——

  A novel synthetic method of 14α-hydroxy-6-oxo-7-ene steroid from 6-oxo-7-ene steroid was developed. The enol acetylation of 7-en-6-one with acetic anhydride in the presence of perchloric acid afforded 6-acetoxy-6, 8 (14)-diene, which on treatment with monoperphthalic acid gave 14α-hydroxy-7-en-6-one. 2β, 3β, 14α-Trihydroxy-5β-cholest-7-en-6-one (XXVIII), the nuclear structure of which is the same as that of ecdysone, was prepared by this method, and the stereochemistry of XXVIII and related compounds was studied.

  开发了一种从6-氧代-7-烯类固醇合成14α-羟基-6-氧代-7-烯类固醇的新方法。在高氯酸存在下，7-en-6-酮与乙酸酐的烯醇乙酰化得到 6-乙酰氧基-6, 8(14)-二烯，用单过苯二甲酸处理后得到 14α-羟基-7-en-6 -一。利用该方法制备了核结构与蜕皮激素相同的2β,3β,14α-三羟基-5β-cholest-7-en-6-one(XXVIII),并对其进行了立体化学分析被研究了。
• ——
  作者：N. V. Kovganko、V. L. Survilo

  DOI：10.1023/a:1021673924353

  日期：——

  22,25-Dideoxyecdysome (1) and 5alpha-22.25-dideoxyecdysone (1a) were prepared from cholesterol via a new scheme using the key intermediates 3beta-chloro-5alpha-bromo-6-ketone 3. 3beta-chloro-7alpha-bromo-6-ketone 4, and 2,7-dien-6-one 7.