11α-hydroxypregna-1,4-diene-3,20-dione | 2417-44-9

• 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: 11α-hydroxypregna-1,4-diene-3,20-dione
• 英文别名: 11α-hydroxy-pregna-1,4-diene-3,20-dione；11α-Hydroxy-pregna-1,4-dien-3,20-dion；11α-Hydroxy-Δ^1,4-pregnadien-dion-(3,20)；11α-Hydroxy-Δ^1,4-pregnadiendion-(3,20)；11α-Hydroxy-3,20-dioxo-Δ^1,4-pregnadien；11alpha-Hydroxypregna-1,4-diene-3,20-dione；(8S,9S,10R,11R,13S,14S,17S)-17-acetyl-11-hydroxy-10,13-dimethyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-3-one
• CAS: 2417-44-9
• 化学式: C₂₁H₂₈O₃
• 分子量: 328.452
• InChiKey: XYVVSFGOAQGVRE-QJSKAATBSA-N

物化性质

• 熔点：
  228-230 °C(Solv: ethanol, 95% (64-17-5))
• 沸点：
  490.2±45.0 °C(Predicted)
• 密度：
  1.17±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  24
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  11α-hydroxypregna-1,4-diene-3,20-dione 以 1,4-二氧六环 为溶剂， 反应 1.0h， 以62%的产率得到2,11α-dihydroxy-4-methyl-19-norpregna-1,3,5(10)-trien-20-one
  参考文献：
  名称：

  Photochemistry of 11.alpha.- and 11.beta.-hydroxy steroidal 1,4-dien-3-ones and 11.alpha.- and 11.beta.-hydroxy steroidal bicyclo[3.1.0]hex-3-en-2-ones in neutral and acidic media

  摘要：

  DOI：

  10.1021/jo01300a012
• 作为产物：
  描述：

  (8S,9S,10S,13S,14S,17S)-17-acetyl-10,13-dimethyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-3-one 生成 11α-hydroxypregna-1,4-diene-3,20-dione
  参考文献：
  名称：

  PETZOLDT, K.;KIESLICH, K.;WEBER, A.;KRIEGER, B.

  摘要：

  DOI：

文献信息

• Microbial Hydroxylation of Hydroxyprogesterones and α-Glucosidase Inhibition Activity of Their Metabolites
  作者：Muhammad Iqbal Choudhary、Muhammad Nasir、Shamsun N. Khan、Muhammad Atif、Rahat A. Ali、Syed M. Khalil、Atta-ur Rahman

  DOI：10.1515/znb-2007-0419

  日期：2007.4.1

  elegans and Fusarium lini yielded 11α,17α- dihydroxypregn-4-ene-3,20-dione (9), and 17α-hydroxypregna-1,4-diene-3,20-dione (10). The structures of the metabolites 3 - 10 were deduced on the basis of spectroscopic methods. Compound 3 was identified as a new metabolite, which exhibited a promising inhibitory activity against the α-glucosidase enzyme.

  11α-羟基孕酮 (1) 与 Cunninghamella elegans、Gibberella fujikuroi、Fusarium lini 和白色念珠菌的微生物转化产生 11α,15α,16α-trihydroxypregn-4-ene-3,20-dione (3), 11α-hydroxy pregnane-3,20-dione (4), 6β,11α-dihydroxypregn-4-ene-3,20-dione (5), 11α-hydroxypregna-1,4-diene-3,20-dione (6), 11α ,17β-dihydroxyandrost-4-en-3-one (7) 和 11α,15α-dihydroxypregn-4-ene-3,20-dione (8)。另一方面，17α-羟基孕酮 (2) 与 Cunninghamella elegans 和 Fusarium
• Studies on a-norsteroids—VI
  作者：Tokuo Kubota、Fumiko Hayashi

  DOI：10.1016/0040-4020(67)85047-6

  日期：1967.1

  The effects of C11-substituents on the hydroxylation of Δ1,4-3-oxosteroids with osmium tetroxide, have been examined. The 11α-substituents, such as 11α-hydroxy, 1α-acetoxy or 11α-methyl-11β-hydroxy groups, result in the selective addition of osmium tetroxide at the Δ4 double bond, giving 4β,5β-dihydroxy-Δ1-3-oxosteroids. On the other hand, the 11-oxo yields exclusively 1α,2α-dihydroxy-Δ4-3-oxosteroids

  C的影响11 -取代基上Δ的羟基化1,4- -3- oxosteroids用四氧化锇，已经被检查。在11α-取代基，如11α羟基，1α乙酰氧基或11α甲基11β-羟基，导致在Δ选择性加成的四氧化锇4双键，给人4β，5β二羟基Δ 1 -3 -氧类固醇。在另一方面中，11-氧代产量只1α，2α二羟基Δ 4 -3- oxosteroids。
• Über Digitanolglykoside, XI: Partialsynthese von Holadyson
  作者：Rudolf Tschesche、Volker Knittel、Günther Snatzke

  DOI：10.1002/cber.19650980636

  日期：1965.6

  Holadyson, C21H28O4, wurde aus 11α-Hydroxy-progesteron synthetisiert und seine Identität mit dem Naturprodukt bewiesen.

  Holadyson，C 21 H 28 O 4，合成11α-羟基-黄体酮和天然产物的围网结构。
• Amino-9,10-secosteroids useful for treating head injury, spinal cord
  申请人：The Upjohn Company

  公开号：US04996318A1

  公开（公告）日：1991-02-26

  The amino-9,10-secosteroids ##STR1## of the present invention contain an amino group attached to the terminal carbon atom of the C.sub.17 -side chain and are useful as pharmaceutical agents for treating a number of conditions including spinal trauma, mild and/or moderate to severe head injury, etc.

  本发明的氨基-9,10-脱氢胆甾类化合物（##STR1##）在C.sub.17-侧链的末端碳原子上附有氨基基团，并可用作治疗多种疾病的药物，包括脊髓损伤、轻度和/或中度至重度头部损伤等。
• Synthesis of C(1)–C(11) oxygen-bridged pregnanes
  作者：Adriana S. Veleiro、Paula J. Taich、Lautaro D. Alvarez、Pablo H. Di Chenna、Gerardo Burton

  DOI：10.1016/j.tetlet.2005.04.052

  日期：2005.6

  A general procedure for the synthesis of 1 alpha,11 alpha- and 1 beta,11 alpha-epoxysteroids is described, using an intramolecular remote functionalization reaction involving the photolysis of 11 alpha-hydroxysteroids in the presence of diacetoxyiodobenzene and iodine. Three 1,11-epoxypregnanes were prepared, two of them (compounds 10 and 14) are conformationally constrained analogues of steroidal hormones, compound 13 is a synthetic precursor of neurosteroids. (c) 2005 Elsevier Ltd. All rights reserved.