pregnenolone | 210692-25-4

• 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: pregnenolone
• 英文别名: 1-[(3R,8R,9R,10S,13R,14R,17R)-3-hydroxy-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]ethanone
• CAS: 210692-25-4
• 化学式: C₂₁H₃₂O₂
• 分子量: 316.484
• InChiKey: ORNBQBCIOKFOEO-UOZQCWKMSA-N

物化性质

• 沸点：
  443.3±45.0 °C(Predicted)
• 密度：
  1.09±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  23
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  pregnenolone 在 三乙基硅烷 、 4-二甲氨基吡啶 、 2,4,5,6-四(9H-咔唑-9-基)异酞腈 、 caesium carbonate 、 N,N'-二环己基碳二亚胺 作用下， 以 乙醚 、 二甲基亚砜 为溶剂， 30.0 ℃ 、101.33 kPa 条件下， 反应 36.0h， 生成 3-(((3R,8R,9R,10S,13R,14R,17R)-17-acetyl-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl)oxy)-2-fluoro-2-methyl-3-oxopropanoic acid
  参考文献：
  名称：

  可见光光氧化还原催化的 C(sp3)-F 键与 CO2 的选择性羧化

  摘要：

  在有价值的化合物的合成中，利用二氧化碳 (CO 2 ) 作为一种无毒且可持续的 C1 来源，因其惰性而极具吸引力和挑战性。在这里，我们报告了 C(sp 3 )-F 键与 CO 2通过可见光光氧化还原催化的新型选择性羧化。各种单、二和三氟烷基芳烃以及 α,α-二氟羧酸酯和酰胺在温和条件下进行此类反应，生成重要的芳基乙酸和 α-氟羧酸，包括几种药物和类似物。值得注意的是，机械研究和 DFT 计算证明了 CO 2的双重作用在这种转变过程中作为电子载体和亲电子试剂。氟化底物将通过富电子的 CO 2自由基阴离子进行单电子还原，这些阴离子是通过连续的氢化物转移还原和氢原子转移过程从 CO 2原位生成的。我们预计我们的发现将成为使用惰性底物（包括木质素和其他生物质）进行更具挑战性的 CO 2利用率的起点。

  DOI：

  10.1016/j.chempr.2021.08.004
• 作为产物：
  描述：

  (R)-1-[(3R,8R,9R,10S,13R,14R,17R)-3-(tert-Butyl-dimethyl-silanyloxy)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]-ethanol 在 Celite 、 四丁基氟化铵 、 sodium acetate 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 24.0h， 生成 pregnenolone
  参考文献：
  名称：

  Neurosteroid Analogues. 6. The Synthesis and GABA_A Receptor Pharmacology of Enantiomers of Dehydroepiandrosterone Sulfate, Pregnenolone Sulfate, and (3α,5β)-3-Hydroxypregnan-20-one Sulfate

  摘要：

  The unnatural enantiomers of dehydroepiandrosterone sulfate (1), pregnenolone sulfate (2), and (3 alpha,5 beta)-3-hydroxypregnan-20-one sulfate (3), compounds 4-6, respectively, were prepared by total steroid synthesis. The enantioselectivity of the compounds as negative modulators of the GABA(A) receptors present in cultured rat hippocampal neurons was examined using electrophysiological methods. Enantioselectivity was found for the inhibitory actions of the dehydroepiandrosterone enantiomers, The IC(50)s for compounds 1 and 4 were 11 +/- 1 and 80 +/- 14 mu M, respectively. Little, if any, enantioselectivity was found for the other two pairs of steroid sulfate inhibitors. The IC(50)s for compounds 2 and 5 were 82 +/- 12 and 76 +/- 27 mu M, respectively. The IC(50)s for compounds 3 and 6 were 39 +/- 7 and 46 +/- 2 mu M, respectively. The results suggest that the sites of action for the androstane and pregnane series of steroid sulfate blockers of GABA-mediated current are different. The observed enantioselectivity for the actions of dehydroepiandrosterone sulfate indicates that its inhibitory actions are mediated via a chiral recognition site and provides new evidence in support of the earlier hypothesis that there is a binding site for this compound on GABA(A) receptors. Conversely, the failure to observe enantioselectivity for the actions of pregnenolone sulfate and steroid sulfate 3 indicates that a chiral recognition site far these steroids does not exist on GABA(A) receptors and suggests that the effects of these compounds on this receptor's function may arise indirectly as a consequence of steroid-induced membrane perturbation.

  DOI：

  10.1021/jm980148h

文献信息

• Carbonylation of α-Aminoalkyl radicals to the direct synthesis of α-Amino acid derivatives
  作者：Le-Cheng Wang、Xiao-Feng Wu

  DOI：10.1016/j.jcat.2023.115193

  日期：2023.12

  α-Amino acid derivatives are indispensable motifs in various areas. Herein, we developed an unprecedented and general α-aminoalkyl carbonylation protocol that activates a variety of inert C–H bonds as native functional handles toward the direct synthesis of various α-amino acid derivatives. The key to the success of this mode is the installation of an appropriate electron-withdrawing group which can

  α-氨基酸衍生物是各个领域不可或缺的基序。在此，我们开发了一种前所未有的通用α-氨基烷基羰基化方案，该方案激活各种惰性C-H键作为直接合成各种α-氨基酸衍生物的天然功能手柄。该模式成功的关键是安装合适的吸电子基团，该基团可以调节α-氨基烷基的亲核性，并为后续的羰基化过程提供匹配的极性。该催化策略具有非常广泛的底物范围和对敏感官能团的优异耐受性，为α-氨基酸衍生物提供了普遍且实用的途径。