5α-pregn-20-en-3β-ol | 33300-02-6

• 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-pregn-20-en-3β-ol
• 英文别名: 5alpha-Pregnene-3beta-ol；(3S,5S,8R,9S,10S,13R,14S,17R)-17-ethenyl-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-ol
• CAS: 33300-02-6
• 化学式: C₂₁H₃₄O
• 分子量: 302.5
• InChiKey: JKTCVURCUCFDGC-DDYSHWNRSA-N

物化性质

• 沸点：
  394.7±11.0 °C(predicted)
• 密度：
  1.035±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  5α-pregn-20-en-3β-ol 在 chromium(VI) oxide 、 硫酸 作用下， 以 丙酮 为溶剂， 生成 17α-pregna-4,20-dien-3-one
  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
• 作为产物：
  描述：

  3β-acetyloxy-20(S)-hydroxy-5αH-pregnane 在 氢氧化钾 、 五氯化磷 作用下， 以 甲醇 为溶剂， 生成 5α-pregn-20-en-3β-ol
  参考文献：
  名称：

  Synthesis of the isomeric 3β-acetoxy-20-chloro-5α-pregnanes

  摘要：

  DOI：

  10.1016/0039-128x(69)90055-5

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。
• Formolysis of 3β-acetoxy-5α-pregnan-20α-yl p-toluenesulfonate
  作者：F.B. Hirschmann、D.M. Kautz、S.S. Deshmane、H. Hirschmann

  DOI：10.1016/s0040-4020(01)91602-3

  日期：1971.1

  In contrast to its 20-epimer, the formolysis of 3β-acetoxy-5α-pregnan-20α-yl tosylate proceeds predominantly without enlargement of the D ring. The products were identified as 17β-methyl-18-nor-5α, 17α-pregn-13-en-3β-yl acetate (2b), 3β-acetoxy-5α-pregnan-20α-yl formate (13), 3β-acetoxy-17-α-methyl-D-homo-5α-androstan-17αβ-yl formate (14). 5α-pregn-20-en-3β-yl acetate (12b) and 3β-acetoxy-5α-pregnan-20β-yl

  与它的20个末端相反，甲苯磺酸3β-乙酰氧基-5α-pregnan-20α-甲苯磺酸酯的形成主要在不扩大D环的情况下进行。产物鉴定为17β-甲基-18-nor-5α，17α-pregn-13-en-3β-乙酸乙烯酯（2b），3β-乙酰氧基-5α-pregnan-20α-甲酸甲酸酯（13），3β-乙酰氧基-17-α-甲基-D-homo-5α-雄烷-17αβ-甲酸甲酸酯（14）。5α-pregn-20-en-3β-乙酸乙烯酯（12b）和3β-乙酰氧基-5α-pregnan-20β-甲酸甲酸酯（15）。在2b降解过程中，制备了两种顺式-13,14二醇，其中一种对具有和不参与氢键合的氢的OH拉伸带具有异常大的Δv。这个大值（99厘米-1）归因于13α，14α-二醇的分子变形。该二醇的这种构型和相对产率将表明2b中13,14双键的β面更易于加入OsO 4和其他试剂。据报道该双键的催化氢化。建议了可
• 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。
• [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 the isomeric 3β-acetoxy-20-chloro-5α-pregnanes
  作者：R Li

  DOI：10.1016/0039-128x(69)90055-5

  日期：1969.4