3b-羟基-5a-孕甾烷-16-烯-20-酮 | 566-61-0

• 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
• 中文名称: 3b-羟基-5a-孕甾烷-16-烯-20-酮
• 英文名称: allopregnenolone
• 英文别名: 3β-hydroxy-5α-pregn-16-en-20-one；5α-pregn-3β-ol-16-en-20-one；3β-Hydroxy-5α-pregn-16-en-20-on；1-[(3S,5S,8R,9S,10S,13S,14S)-3-hydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]ethanone
• CAS: 566-61-0
• 化学式: C₂₁H₃₂O₂
• mdl: MFCD06738065
• 分子量: 316.484
• InChiKey: SFXPZLCQRZASKK-CKBUFISISA-N

物化性质

• 熔点：
  202-204 °C
• 沸点：
  443.7±45.0 °C(Predicted)
• 密度：
  1.077±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于氯仿（少许）、甲醇（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 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：

  3b-羟基-5a-孕甾烷-16-烯-20-酮 在 2,2,6,6-四甲基哌啶氧化物 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以78%的产率得到3,20-Diketo-5α-pregn-16-en
  参考文献：
  名称：

  Effective and mild method for converting 3β-hydroxysteroids to 3-keto steroids via DDQ/TEMPO

  摘要：

  A mild and efficient oxidation of 3 beta-hydroxysteroids to the corresponding 3-keto steroids can be carried out at room temperature, using DDQ in the presence of catalytic TEMPO. Oxidation of saturated 3 beta-hydroxysteroids gave the corresponding ketones in excellent yield. The 5-unsaturated 3 beta-hydroxysteroids are oxidized selectively to 4-en-3-one or 4,6-diene-3-one derivatives according to the amount of DDQ in reaction. This is a good method for the synthesis of 4,6-diene-3-one from the corresponding 3 beta-hydroxy-5-ene steroids. Meanwhile, configurations of the oxidation compounds 2a, 2b, 3h, 2c, 2f and 2g were identified by X-ray diffraction. A possible mechanism is presented and discussed. (C) 2015 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2015.01.010
• 作为产物：
  描述：

  (R)-5-acetoxy-4-methyl-valeric acid-(3β-acetoxy-20-oxo-5α-pregnan-16β-yl ester) 在 氢氧化钾 作用下， 生成 3b-羟基-5a-孕甾烷-16-烯-20-酮
  参考文献：
  名称：

  Sterols. CXVII. Sapogenins. XLVI. The Structure of Pseudosapogenins

  摘要：

  DOI：

  10.1021/ja01848a039

文献信息

• SYSTEM FOR DELIVERING THERAPEUTIC AGENTS INTO LIVING CELLS AND CELLS NUCLEI
  申请人：DELIVERSIR LTD.

  公开号：US20160039850A1

  公开（公告）日：2016-02-11

  The present invention relates to a novel delivery system for delivering therapeutic agents into living cells, and more particularly, to novel chemical moieties that are designed capable of targeting and/or penetrating cells or other targets of interest and further capable of binding therapeutic agents to be delivered to these cells, and to delivery systems containing same.

  本发明涉及一种新型递送系统，用于将治疗剂递送到活细胞中，更具体地说，涉及设计用于靶向和/或穿透细胞或其他感兴趣目标的新型化学基团，进一步能够将治疗剂结合到这些细胞中以进行递送，并涉及含有相同化学基团的递送系统。
• Multi-triggered self-immolative dendritic compounds
  申请人：Amir Jacob Roey

  公开号：US20060269480A1

  公开（公告）日：2006-11-30

  Novel self-immolative dendritic compounds which have a plurality of cleavable trigger units and hence can release a chemical moiety at their focal point upon a multi-triggering mechanism are disclosed. The novel self-immolative dendritic compounds are gated by a molecular logic gate, being either an AND or OR logic gate and hence can be beneficially used in a variety of biological, chemical and physical applications. Processes of preparing, compositions containing and methods utilizing the novel dendritic compounds are further disclosed.

  披露了新型的自消融树枝状化合物，它们具有多个可裂解的触发单元，因此可以在多点触发机制下在其焦点处释放化学基团。这些新型的自消融树枝状化合物由分子逻辑门控制，该逻辑门为AND或OR逻辑门，因此可以有益地用于各种生物学、化学和物理应用中。进一步披露了制备、含有新型树枝状化合物的组合物以及使用这些树枝状化合物的方法。
• Synthesis of hydroxylated steroid hormones via conjugate addition of a silyl-cuprate reagent
  作者：Diana Garside、David N. Kirk、Norman M. Waldron

  DOI：10.1016/0039-128x(94)90102-3

  日期：1994.12

  several hydroxylated steroids via conjugate addition of Fleming's silyl-cuprate reagent, (PhMe2Si)2CuLi, a masked hydroxyl group, to the appropriate enone was studied. By this means 7 alpha-hydroxytestosterone (7) was obtained in good yield from 17 beta-hydroxyandrosta-4,6-dien-3-one (1a), though similar reactions on 17 beta-hydroxyandrosta-1,4-dien-3-one (8) gave a low yield of 1 alpha-hydroxytestosterone

  研究了通过将Fleming的甲硅烷基-杯酸酯试剂（PhMe2Si）2CuLi，一种被掩蔽的羟基缀合到适当的烯酮中来合成几种羟基化的类固醇。通过这种方法，从17个β-羟基雄甾烯-4,6-dien-3-one（1a）以良好的收率获得了7个α-羟基睾丸激素（7），尽管对17个β-羟基雄甾烯-1,4-dien-3的反应相似-一（8）产生低产率的1α-羟基睾丸酮（13）的主要原因是苯基甲硅烷基中间体向卤代硅烷的转化率低。以类似的方式从3 beta-hydroxy-5 alpha-pregn-16-en-20-one和5 alpha-cholestane-1获得3 beta，16 alpha-Dihydroxy-5 alpha-pregnan-20-one（18b）。通过共轭加成甲硅烷基，还原羰基官能团，由1-en-3-one（14）生成alpha，3 alpha-diol（17），
• Geminal dimetallic compounds
  作者：F. Bertini、P. Grasselli、G. Zubiani、G. Cainelli

  DOI：10.1016/s0040-4020(01)92998-9

  日期：1970.1

  The reaction of 1,1-dihalo-alkanes with magnesium and magnesium amalgam has been studied. Methylene bromide and iodide yield, under suitable conditions, a stable solution of methylene magnesium halide which easily olefinates aldehydes and ketones affording the corresponding methylenic olefins in good yields. Other alkylidene halides, under the conditions studied, do not give any stable geminal dimagnesium

  已经研究了1，1-二卤代烷烃与镁和镁汞齐的反应。在合适的条件下，溴甲烷和碘化物的亚甲基卤化物的稳定溶液可以很容易地使醛和酮烯化，从而以高收率得到相应的亚甲基烯烃。尽管在亚烷基卤化物，羰基化合物和镁汞齐之间的原位反应过程中可能存在双晶种，但在研究的条件下，其他亚烷基卤化物不会产生任何稳定的双结晶二铵化合物。提出了考虑到大多数这种已知反应的一般羰基烯烃化方案。
• Grignard reagent induced tandem semipinacol rearrangement/ketone addition reaction of 20S-hydroxy-5α-pregnane-16(17)-epoxide
  作者：Chun-Xi Huang、Yong Shi、Jing-Rong Lin、Rong-Hua Jin、Wei-Sheng Tian

  DOI：10.1016/j.tetlet.2011.05.122

  日期：2011.8

  A Grignard reagent induced tandem semipinacol rearrangement/chelation-controlled ketone addition process, which converts 20S-hydroxy-5α-pregnane-16(17)-epoxide into an unusual C20-substituted 17S-pregnane-3S,16R,20S-triol, is described.

  Grignard试剂诱导串联半松果醇重排/螯合控制的酮添加过程，该过程将20 S-羟基-5α-孕烷-16（17）-环氧转化为不寻常的C20取代的17 S-孕烷3 S，16 R，20描述了S-三醇。