4-pregnene-3β,20β-diol | 7217-07-4

• 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: 4-pregnene-3β,20β-diol
• 英文别名: 4-pregnene-3β,20(R)-diol；4-pregnene-3S,20R-diol；pregn-4-ene-3β,20β_F-diol；Pregn-4-en-3β,20β_F-diol；20β,3β-Dihydroxy-Δ⁴-pregnen；Pregn-4-en-3β,(20R)-diol；4-Pregnene-3beta,20beta-diol；(3S,8S,9S,10R,13S,14S,17S)-17-[(1R)-1-hydroxyethyl]-10,13-dimethyl-2,3,6,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol
• CAS: 7217-07-4
• 化学式: C₂₁H₃₄O₂
• 分子量: 318.5
• InChiKey: IBMZAHKIAAJREF-NFJVIFTASA-N

物化性质

• 熔点：
  163-172 °C
• 沸点：
  449.5±18.0 °C(Predicted)
• 密度：
  1.09±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  23
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-pregnene-3β,20β-diol 在 盐酸 作用下， 生成 20β-hydroxy-pregna-3,5-diene
  参考文献：
  名称：

  Camerino; Alberti, Gazzetta Chimica Italiana, 1955, vol. 85, p. 51,54

  摘要：

  DOI：
• 作为产物：
  描述：

  4-孕烯-3beta-ol-20-酮 在 sodium tetrahydroborate 、 sodium hydroxide 作用下， 以 水 、 乙酸乙酯 为溶剂， 反应 1.5h， 以98%的产率得到4-pregnene-3β,20β-diol
  参考文献：
  名称：

  NaBH4在PANF固定化季铵盐催化下的水中NaBH4高效还原羰基，叠氮化物和苄基卤化物

  摘要：

  制备了一系列聚丙烯腈纤维负载的季铵盐（PANF-QAS），并将其用于以NaBH4作为还原剂催化还原水中的醛，酮，叠氮化物和苄基卤化物。

  DOI：

  10.1039/c5gc02621k

文献信息

• Synthesis of 17β-[(1S)-1-hydroxy-2-propynyl]- and 17β-[(1R)-1-hydroxy-2-propynyl]androst-4--en-3-one. Potential suicide substrates of 20α- and 20β- hydroxysteroid dehydrogenases
  作者：Douglas F. Covey

  DOI：10.1016/0039-128x(79)90048-5

  日期：1979.8

  The title compounds have been synthesized for evaluation as potential suicide substrates of 20 alpha- and 20 beta-hydroxysteroid dehydrogenases. Synthesis was achieved by the following route. Acetylenedimagnesium bromide was reacted with 3 beta-hydroxyandrost-4-ene-17 beta-carboxaldehyde to give 17 beta-[(1R,S)-1-hydroxy-2-propynyl] androst-4-en-3 beta-ol. Separation of the R and S diols was achieved

  已合成标题化合物，以评估其为20种α-和20种β-羟类固醇脱氢酶的潜在自杀底物。通过以下途径完成合成。乙炔二溴化镁与3个β-羟基雄烯-4-烯-17β-甲醛反应生成17个β-[（（R，S）-1-羟基-2-丙炔基] androst-4-en-3β-醇。R和S二醇的分离通过HPLC（高压液相色谱）实现。用琼斯试剂在0度选择性氧化3β-羟基，得到标题化合物。用Jones试剂进一步氧化将每种炔醇转化为共轭炔酮17β-（1-氧代-2-丙炔基）和rost-4-en-3-one。
• Camerino; Patelli, Farmaco, Edizione Scientifica, 1956, vol. 11, p. 579,584
  作者：Camerino、Patelli

  DOI：——

  日期：——
• Partial reduction of steroid hormones and related substances
  作者：J. K. Norymberski、Gilbert F. Woods

  DOI：10.1039/jr9550003426

  日期：——
• Neurosteroid Analogues. 4. The Effect of Methyl Substitution at the C-5 and C-10 Positions of Neurosteroids on Electrophysiological Activity at GABA_A Receptors
  作者：Mingcheng Han、Charles F. Zorumski、Douglas F. Covey

  DOI：10.1021/jm960304p

  日期：1996.1.1

  A series of analogues of the neuroactive steroids 3 alpha-hydroxy-5 alpha-pregnan-20-one and 3 alpha-hydroxy-5 beta-pregnan-20-one were studied to elucidate the mode of binding of 5 alpha- and 5 beta-reduced steroids to steroid binding sites on GABA(A) receptors. Analogues which were either 3 alpha-hydroxy-20-ketosteroids or 3 alpha-hydroxysteroid-17 beta-carbonitriles and which contained various methyl group substitution patterns at C-5 and C-10 were prepared. Evaluations utilized whole-cell patch clamp electrophysiological methods carried out on cultured rat hippocampal neurons, and the results obtained with the rigid 17 beta-carbonitrile analogs were analyzed using molecular modeling methods. The molecular modeling results provide a rationale for the observation that the configuration of the hydroxyl group at C-3 is a greater determinant of anesthetic potency than the configuration of the A,B ring fusion at C-5. The electrophysiological results identify steric restrictions for the space that can be occupied in 5 alpha- and 5 beta-reduced steriod modulators of GABA(A) receptors in the regions of space proximate to the steroid C-5, C-10, and possibly C-4 positions. This information is useful for the development of nonsteroidal analogues that can modulate GABA(A) receptors via interactions at steroid binding sites.
• Synthesis and characteristics of allylic 4-pregnene-3,20-diols found in gonadal and breast tissues
  作者：J.P Wiebe、Vinod Dave、J.B Stothers

  DOI：10.1016/0039-128x(86)90095-4

  日期：1986.4

  Recently several allylic steroids have been found in gonadal and breast tissues. In order to establish their presence and identity in tissues and determine the possible biological properties, a method for the synthesis of 4-pregnene-3 alpha,20 alpha-diol, 4-pregnene-3 alpha, 20 beta-diol, 4-pregnene-3 beta,20 alpha-diol, and 4-pregnene-3 beta,20 beta-diol was developed using 4-pregnene-3,20-dione (progesterone) as substrate and freshly-prepared aluminum isopropoxide in isopropyl alcohol as reducing agent. The yields were about 19%, 30%, 13%, and 38% for the 3 alpha,20 alpha-, 3 alpha,20 beta-, 3 beta,20 alpha-, and 3 beta,20 beta-diols, respectively. The structures and stereochemistry of these diols were established using proton and carbon NMR spectroscopy and infrared and mass spectrometry.