5α-Pregna-1,20-dien-3-on | 65754-62-3

• 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: 5α-Pregna-1,20-dien-3-on
• 英文别名: 5alpha-Pregna-1,20-dien-3-one；(5S,8S,9S,10R,13R,14S,17R)-17-ethenyl-10,13-dimethyl-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one
• CAS: 65754-62-3
• 化学式: C₂₁H₃₀O
• 分子量: 298.469
• InChiKey: JIFKGXKDITUDPD-PMJYHDSJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  5α-Pregna-1,20-dien-3-on 在 palladium on activated charcoal 氢气 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 苯 为溶剂， 生成 (5α)-pregnan-3-one
  参考文献：
  名称：

  5α-pregna-1, 20-dien-3-one and related compounds from a soft coral

  摘要：

  Four unusual pregnane derivatives, 5alpha-pregna-1,20-dien-3-one (1), 1,4,20-pregnatrien-3-one (3), 5alpha-pregn-20-en-3alpha-o1 o-acetate (4), and 5alpha-pregn-20-en-1alpha,3alpha-diol 3-acetate (6) have been isolated from an unidentified soft coral from Canton Island.

  DOI：

  10.1016/0039-128x(77)90028-9
• 作为产物：
  描述：

  pregna-20-en-3-one 生成 5α-Pregna-1,20-dien-3-on
  参考文献：
  名称：

  Synthesis of 5α-pregna-1, 20-dien-3-one

  摘要：

  5ALPHA-Pregna-1,20-dien-3-one has been synthesized from 3beta-hydroxy-5alpha-pregnan-20-one by reaction of the tosylhydrazone with butyllithium to introduce the vinyl moiety. Oxidation of the alcohol and treatment of the anion of the resulting ketone with benzeneselenenyl chloride gave the 2-phenylseleno derivative. This afforded the conjugated enone on oxidative elimination.

  DOI：

  10.1016/0039-128x(77)90029-0

文献信息

• FRAGRANCE COMPOSITIONS AND OTHER COMPOSITIONS WHICH CONTAIN NATURALLY OCCURRING SUBSTANCES FOUND IN CORALS
  申请人：JENNINGS-WHITE Chloe

  公开号：US20090075964A1

  公开（公告）日：2009-03-19

  This invention is generally related to the fields of fragrance compositions, personal care products, and home consumer products. This invention also relates to 20-pregnenes, in particular those found naturally occurring in corals and which affect mood in humans, to the incorporation of these 20-pregnene compounds into various compositions, and to methods of affecting the mood of individuals using such compounds.

  这项发明通常与香精配方、个人护理产品和家用消费品领域相关。该发明还涉及20-孕烯类化合物，特别是那些在珊瑚中自然存在且对人类情绪产生影响的化合物，将这些20-孕烯类化合物纳入各种配方中，以及利用这些化合物影响个体情绪的方法。
• Fragrance Compositions and Other Compositions Which Contain Naturally Occurring Substances Found in Corals
  申请人：Human Pheromone Sciences, Inc.

  公开号：US20140045805A1

  公开（公告）日：2014-02-13

  This invention is generally related to the fields of fragrance compositions, personal care products, and home consumer products. This invention also relates to 20-pregnenes, in particular those found naturally occurring in corals and which affect mood in humans, to the incorporation of these 20-pregnene compounds into various compositions, and to methods of affecting the mood of individuals using such compounds.

  本发明通常涉及香料组合物、个人护理产品和家庭消费品领域。本发明还涉及20-孕烷类化合物，特别是自然存在于珊瑚中并影响人类情绪的化合物，将这些20-孕烷类化合物纳入各种组合物中，以及利用这些化合物影响个体情绪的方法。
• An unusual spinaceamine-bearing pregnane from a soft coral Scleronephthya sp. inhibits the migration of tumor cells
  作者：Wei Cheng、Zhen Liu、Yang Yu、Leen van Ofwegen、Peter Proksch、Siwang Yu、Wenhan Lin

  DOI：10.1016/j.bmcl.2017.04.058

  日期：2017.6

  An unprecedented spinaceamine-bearing pregnane namely scleronine (1) was isolated from a Chinese soft coral Scleronephthya sp. Its structure was determined on the basis of 1D and 2D NMR spectroscopic analyses in association with the HRESIMS data, while the absolute configurations were deduced by the single-crystal X-ray diffraction analysis. In addition, a dehydrogenated analogue (3) was synthesized through six steps with pregna-1,20-dien-3-one (2) as a precursor. The significantly inhibitory effects of 1 and 3 against the migration of tumor cells A549 and B16 accompanying the down-regulation of key genes (TGF beta, TNF alpha, IL-1 beta, and IL-6) were observed. These findings suggested that both 1 and 3 are potential for therapeutic usage aiming at cancer metastasis inhibition. (C) 2017 Elsevier Ltd. All rights reserved.
• [EN] FRAGRANCE COMPOSITIONS AND OTHER COMPOSITIONS WHICH CONTAIN NATURALLY OCCURRING SUBSTANCES FOUND IN CORALS<br/>[FR] COMPOSITIONS DE PARFUMS ET AUTRES COMPOSITIONS QUI CONTIENNENT DES SUBSTANCES D'ORIGINE NATURELLE SE TROUVANT DANS LES CORAUX
  申请人：HUMAN PHEROMONE SCIENCES INC

  公开号：WO2009039103A2

  公开（公告）日：2009-03-26

  This invention is generally related to the fields of fragrance compositions, personal care products, and home consumer products. This invention also relates to 20-pregnenes, in particular those found naturally occurring in corals and which affect mood in humans, to the incorporation of these 20-pregnene compounds into various compositions, and to methods of affecting the mood of individuals using such compounds.
• Synthesis of 5α-pregna-1, 20-dien-3-one
  作者：Steven R. Schow、Trevor C. McMorris

  DOI：10.1016/0039-128x(77)90029-0

  日期：1977.9

  5ALPHA-Pregna-1,20-dien-3-one has been synthesized from 3beta-hydroxy-5alpha-pregnan-20-one by reaction of the tosylhydrazone with butyllithium to introduce the vinyl moiety. Oxidation of the alcohol and treatment of the anion of the resulting ketone with benzeneselenenyl chloride gave the 2-phenylseleno derivative. This afforded the conjugated enone on oxidative elimination.