11beta-Hydroxyestrone | 6803-21-0

• 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: 11beta-Hydroxyestrone
• 英文别名: 3,11β-dihydroxyestra-1,3,5(10)-trien-17-one；11β-hydroxyestrone；3,11β-dihydroxy-estra-1,3,5(10)-trien-17-one；3,11β-Dihydroxy-oestra-1,3,5(10)-trien-17-on；1,3,5(10)-ESTRATRIEN-3,11-beta-DIOL-17-ONE；(8S,9S,11S,13S,14S)-3,11-dihydroxy-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-one
• CAS: 6803-21-0
• 化学式: C₁₈H₂₂O₃
• 分子量: 286.371
• InChiKey: IGSYRIQHXYIOHU-YDRHNJASSA-N

物化性质

• 熔点：
  255-258 °C
• 沸点：
  493.2±45.0 °C(Predicted)
• 密度：
  1.249±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  21
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  11beta-Hydroxyestrone 在 potassium hydride 、 potassium carbonate 、 对甲苯磺酸 作用下， 以 甲醇 、 氯仿 、 甲苯 、 苯 为溶剂， 反应 31.5h， 生成 3-benxyloxy-11β-butoxy-17,17-ethylenedioxyestra-1,3,5(10)-triene
  参考文献：
  名称：

  Nonpolar and Short Side Chain Groups at C-11β of Estradiol Result in Antiestrogens

  摘要：

  We have previously found that esters of 11beta-estradiol carboxylates are transformed from an estrogen into an antiestrogen when the 11beta-side chain is increased in length from four to five non-hydrogen atoms (n greater than or equal to 5). To understand the structural requirements for this transformation and obtain metabolically stable analogues that are not susceptible to esterase cleavage, we have synthesized other compounds having an 11beta-side chain composed of other functional groups: ketones, amides, ethers, and thiono esters. With the exception of amides, which bind poorly to the estrogen receptor (ER), all of these compounds exhibit antiestrogenic action when the side chain length is n greater than or equal to 5. Ethers (n greater than or equal to 5), studied in more detail, inhibit the action of estradiol with either ERalpha or ERbeta. In rat uteri they are estrogen antagonists/weak agonists and decrease the concentration of cholesterol in blood (an hepatic estrogenic action). Thus, these short chain and nonpolar 11beta-analogues of estradiol have tissue specific antiestrogenic/estrogenic actions, characteristics of selective estrogen receptor modulators.

  DOI：

  10.1021/jm049352x
• 作为产物：
  描述：

  1,4-雄二烯-11-beta-醇-3,17-二酮 在 mineral oil 作用下， 生成 11beta-Hydroxyestrone
  参考文献：
  名称：

  Preparation and Reactions of 11-Substituted 1,3,5(10)-Estratrienes.¹ I. 11-Oxygenated Estrones and Estradiols

  摘要：

  DOI：

  10.1021/ja01542a045

文献信息

• Efficient oxidative ipso-fluorination of para-substituted phenols using pyridinium polyhydrogen fluoride in combination with hypervalent iodine(III) reagents
  作者：Omar Karam、Agnès Martin-Mingot、Marie-Paule Jouannetaud、Jean-Claude Jacquesy、Alain Cousson

  DOI：10.1016/j.tet.2004.05.083

  日期：2004.7

  4-fluorocyclohexa-2,5-dienones in a good yield. (R,S)-1,1′-Bi-5,6,7,8-tetrahydro-2-naphthol (and its monoacetate) yields atropoisomeric fluorocyclohexadienones. The 4-substituted carbamate open-chain phenols were readily converted to fluorohydroindolenone and fluorohydroquinolenone derivatives by intramolecular conjugate addition.

  二乙酰氧基碘苯（PIDA）和双（三氟乙酰氧基）碘苯（PIFA）在吡啶鎓多氟化氢（PPHF）的存在下可有效地氟化对位取代的苯酚，从而以良好的方式生成各种4-氟环己-2,5-二烯酮屈服。（R，S）-1，1′-Bi-5，6，7，8-四氢-2-萘酚（及其单乙酸酯）产生阻转异构的氟代环己二酮。通过分子内共轭物加成，将4-取代的氨基甲酸酯开链酚容易地转化为氟代氢吲哚酮和氟代氢醌烯酮衍生物。
• Synthesis of estrogen sulfamates: Compounds with a novel endocrinological profile
  作者：Sigfrid Schwarz、Ina Thieme、Margit Richter、Bernd Undeutsch、Harry Henkel、Walter Elger

  DOI：10.1016/s0039-128x(96)00200-0

  日期：1996.12

  generally applicable and convenient methods for the multigram synthesis of these derivatives are desirable. Numerous estra-1,3,5(10)-trienes derived from estrone, estradiol. 14 alpha,15 alpha-methylenestradiol, ethinylestradiol, and estriol have been esterified with sulfamoyl chloride and N-methylsulfamoyl chloride by a novel approach involving the use of 2,6-di-tert-butylpyridines as bases and chemoselective

  口服硫酸雌激素是有希望的激素。因此，期望用于这些衍生物的多谱图合成的普遍适用且方便的方法。衍生自雌酮，雌二醇的大量estra-1,3,5（10）-三烯。已通过一种新颖的方法将氨磺酰氯和N-甲基氨磺酰氯与14α，15α-亚甲基雌二醇，乙炔雌二醇和雌三醇酯化，该新颖方法涉及使用2,6-二叔丁基吡啶作为碱和化学选择性羟基保护基。这些途径通过原位产生的氮杂亚砜来避免酯的非选择性形成和副反应。为了进行毒理学和临床研究，使用二甲基甲酰胺作为溶剂和碱，开发了一种100 g规模的氨基磺酸雌酮的新合成方法。
• Stereochemistry of Steroids containing Aromatic A-Ring. II. Reaction of 9α, 11α-Epoxyestrone.
  作者：Hiroko Hasegawa、Shigeo Nozoe、Kyosuke Tsuda

  DOI：10.1248/cpb.11.1037

  日期：——

  The reduction of 3-hydroxy-9α, 11α-epoxyestra-1, 3, 5 (10)-trien-17-one (III) with lithium aluminum hydride gave estra-1, 3, 5 (10)-triene-3, 11α, 17β-triol. The reaction of III with hydrogen chloride in methanol yielded 3-hydroxy-9β-estra-1, 3, 5 (10)-triene-11, 17-dione (IXa). On the other hand, the reaction in chloroform afforded 9ξ-chloro-3, 11α-dihydroxyestra-1, 3, 5 (10)-trien-17-one (VIIIa). With alkali 3-hydroxyestra-1, 3, 5 (10)-triene-11, 17-dione (Va) is converted into 9β-isomer (IXa).

  3-羟基-9α,11α-环氧雌甾-1,3,5(10)-三烯-17-酮（III）与氢化铝锂反应生成雌甾-1,3,5(10)-三烯-3,11α,17β-三醇。III与甲醇中的氯化氢反应生成3-羟基-9β-雌甾-1,3,5(10)-三烯-11,17-二酮（IXa）。另一方面，在氯仿中的反应生成9ξ-氯-3,11α-二羟基雌甾-1,3,5(10)-三烯-17-酮（VIIIa）。在碱的作用下，3-羟基雌甾-1,3,5(10)-三烯-11,17-二酮（Va）转化为9β-异构体（IXa）。
• Effect of 11β-substituents on the regioselective chlorination of estrogens with 2,3,4,5,6,6-hexachloro-2,4-cyclohexadienone
  作者：Hasrat Ali、Johan E. van Lier

  DOI：10.1016/0039-128x(94)90065-5

  日期：1994.8

  The reaction of 11 beta-substituted estrogens with 2,3,4,5,6,6-hexachloro-2,4-cyclohexadienone affords exclusively ortho-substituted monochlorinated products including a major 4-chloro and a minor 2-chloro derivative. In the absence of an 11 beta-substituent, regioselectivity is lost, resulting in a mixture of 10 beta- and ortho-chlorinated products.
• Structure-activity relationships of four 11-hydroxyestrones isomeric at the C-9 and C-11 positions
  作者：R. Bruce Gabbard、Leslie F. Hamer、Albert Segaloff

  DOI：10.1016/s0039-128x(81)90234-8

  日期：1981.3

  The synthesis of 11 alpha-hydroxyestrone, 11 alpha-hydroxy-9 beta-estrone, and 11 beta-hydroxy-9 beta-estrone are presented. The reduction of 11-keto-9 beta-estrone 17-ethyleneketal by sodium in ethanol or sodium borohydride resulted in 11-hydroxy-9 beta-estrones. The 11-hydroxyl group configurations were opposite to expectations: sodium in boiling ethanol afforded the axial 11 beta-hydroxy-9 beta-estrone, while sodium borohydride in boiling tetrahydrofuran gave the equatorial 11 alpha-hydroxy-9 beta-estrone. In immature rat uterotropic bioassays using subcutaneous injections, 11 alpha-hydroxyestrone was 2 times as active as 11 alpha-hydroxy-9 beta-estrone, and 11 beta-hydroxyestrone was 10 times as active as 11 beta-hydroxy-9 beta-estrone.