11α,15β-dihydroxypregn-4-ene-3,20-dione | 82538-36-1

• 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,15β-dihydroxypregn-4-ene-3,20-dione
• 英文别名: 11α,15β-dihydroxypregn-4-en-3,20-dione；11α,15β-dihydroxyprogesterone；11α,15β-Dihydroxy-pregn-4-en-3,20-dion；(8S,9S,10R,11R,13S,14S,15R,17S)-17-acetyl-11,15-dihydroxy-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one
• CAS: 82538-36-1
• 化学式: C₂₁H₃₀O₄
• 分子量: 346.467
• InChiKey: BXGCPPYCSCLHER-YWFCDVSRSA-N

物化性质

• 沸点：
  528.6±50.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  25
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  74.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  11α,15β-dihydroxypregn-4-ene-3,20-dione 在 palladium on barium sulfate 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 三甲基氯硅烷 、 氯仿 、 氢气 、 sodium hydride 、 二异丁基氢化铝 、 potassium 2-methylbutan-2-olate 、 对甲苯磺酸 、 sodium thiosulfate 、 溶剂黄146 、 三乙胺 、 sodium iodide 作用下， 以 四氢呋喃 、 吡啶 、 乙醇 、 二氯甲烷 、 乙酸酐 、 乙酸乙酯 、 甲苯 、 乙腈 、 苯 为溶剂， 反应 93.5h， 生成 (24E)-3β,11α,15β,29-tetrahydroxystigmasta-5,24(28)-diene
  参考文献：
  名称：

  脱氢oogoniol，Achlya的女性激活激素的合成：黄体酮途径。

  摘要：

  脱氢-oogoniol（3 beta，11 alpha，15 beta，29-tetrahydroxystigmasta-5,24（28）（E）-dien-7-one）的结构是水模Achlya的一种女性激活激素。综合确认。起始原料是孕酮，它通过用巨大的曲霉（ATCC 10059）进行微生物羟基化反应而转化为11α，15β-二羟基衍生物。通过维蒂希和霍纳-埃蒙斯反应以逐步的方式构建侧链，然后通过烯丙基氧化引入C-7酮。合成化合物的生物活性与天然激素相同。

  DOI：

  10.1016/0039-128x(89)90019-6
• 作为产物：
  描述：

  progesterone 生成 11α,15β-dihydroxypregn-4-ene-3,20-dione
  参考文献：
  名称：

  11, 15-dioxygenated progesterones

  摘要：

  公开号：

  US02881189A1

文献信息

• Microbial Hydroxylation of Pregnenolone Derivatives
  作者：Muhammad Iqbal Choudhary、Iffat Batool、Syed Adnan Ali Shah、Sarfraz Ahmad Nawaz、Atta-ur-Rahman

  DOI：10.1248/cpb.53.1455

  日期：——

  Pregnenolone and pregnenolone acetate were incubated with the fungi Cunninghamella elegans, Rhizopus stolonifer and Gibberella fujikuroi. Incubation of with C. elegans yielded metabolites, 3beta,7beta,11alpha-trihydroxypreg-5-en-20-one, 3beta,6alpha,11alpha,12beta,15beta-pentahydroxypreg-4-en-20-one and 3beta,6beta,11alpha-trihydroxypreg-4-en-20-one, while incubation with G. fujikuroi yielded two known

  将孕烯醇酮和醋酸孕烯醇酮与秀丽线虫Cunninghamella elegans，根霉Rhizopus stolonifer和藤本赤霉菌Gibberella fujikuroi一起孵育。与秀丽隐杆线虫共孵育产生代谢物，3beta，7beta，11alpha-三羟基preg-5-en-20-one，3beta，6alpha，11alpha，12beta，15beta-五羟基preg-4-en-20-one和3beta，6beta，11alpha -trihydroxypreg-4-en-20-one，与藤蔓假丝酵母（G. fujikuroi）孵育时，会产生两种已知的代谢产物：3beta，7beta-dihydroxypregn-5-en-20-one和6beta，15beta-dihydroxypreg-4-ene-3,20- dione。代谢物和被发现是新的。秀丽隐杆线虫的发酵产生了四种已知的氧化代谢产物，雄甾烯-1
• Garai, Subhadra; Banerjee, Sukdeb; Mahato, Shashi B., Journal of Chemical Research - Part S, 1995, # 10, p. 408 - 409
  作者：Garai, Subhadra、Banerjee, Sukdeb、Mahato, Shashi B.

  DOI：——

  日期：——
• Novel metabolites of dehydroepiandrosterone and progesterone obtained in Didymosphearia igniaria KCH 6670 culture
  作者：Tomasz Janeczko、Alina Świzdor、Jadwiga Dmochowska-Gładysz、Agata Białońska、Zbigniew Ciunik、Edyta Kostrzewa-Susłow

  DOI：10.1016/j.molcatb.2012.05.009

  日期：2012.10

  Dehydroepiandrosterone (DHEA) (10) and its five derivatives: testosterone (1), androstenedione (2), 17 alpha-methyltestosterone (6), progesterone (13) and pregnenolone (14) were subjected to microbial transformation by the filamentous fungus Didymosphaeria igniaria KCH 6670. The predominant metabolism of the incubated 5-ene steroids (10 and 14) occurred through 3 beta-hydroxy-steroid dehydrogenase/5.4-en isomerase pathways resulting in the generation of a 4-en-3-oxo system on ring-A. The transformations of C-19 steroids (1, 2, and 10) included a hydroxylation at 7 alpha position, ketone-alcohol interconversion at C-17 and reduction of the double bond at C-4 and 3-keto group to the 3 beta-alcohol with 5 alpha-stereochemistry at A/B ring. D. igniaria also carried out 6(7)-dehydrogenation and 6,7 beta-epoxidation during transformation of DHEA. Under these conditions transformation of DHEA (10) gave four products: 7 alpha-hydroxyandrost-4-en-3,17-dione (4), 17 beta-hydroxyandrost-4,6-dien-3-one (11), 17 beta-hydroxyandrost-6 beta-epoxy-4-en-3-one (12) and 3 beta,17 beta-dihydroxy-5 alpha-androstane (5). The compounds 11 and 12 are identified as DHEA metabolites for the first time. The transformation of C-21 steroids (13 and 14) led to the mixture of mono-(mainly 11 alpha- and 15 beta-) and dihydroxy- (7 alpha,15 beta-: 14 alpha,15 beta-; 11 alpha,15 beta-; 11 alpha,14 alpha-) products. 7 alpha,15 beta-Dihydroxypregnan-4-en-3,20-dione (18) and 14 alpha,15 beta-dihydroxypregnan-4-en-320-dione (19) were found to be new compounds. The main product of transformation of 17 alpha-methyltestosterone (6) was 12 beta-hydroxy-17 alpha-methyltestosterone (7). The results of these transformations demonstrate the dependence of hydroxylation position on the structure of steroid nucleus. (c) 2012 Elsevier B.V. All rights reserved.
• Chick oviduct progesterone receptor binding of 15β,17-dihydroxyprogesterone and its analogues
  作者：Michael E. Baker、Trevor C. McMorris、Linda S. Terry、Susan E. Barrow、Diana L. Villanueva

  DOI：10.1016/0039-128x(84)90034-5

  日期：1984.2

  We have tested derivatives of progesterone obtained by fermentation with Aspergillus giganteus for relative binding affinity for the progesterone receptor of chick oviduct. Our studies show that hydroxyl and oxo substitutents at C-11 and C-15 of progesterone significantly decrease the hormone's affinity for the progesterone receptor. The loss in affinity on introduction of a C-15 hydroxyl in 17-hydroxyprogesterone is restored by acetylation to 15 beta-acetoxy-17 hydroxyprogesterone. The latter compound may have some potential as an in vivo agent.
• Synthesis of dehydrooogoniol, a female-activating hormone of Achlya
  作者：Trevor C. McMorris、Phu Huu Le、Martin W. Preus、Steven R. Schow、Gary R. Weihe

  DOI：10.1021/jo00167a059

  日期：1983.9