3,11β,17α,21-tetraacetoxy-3,5-pregnadiene-20-one | 991-08-2

• 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: 3,11β,17α,21-tetraacetoxy-3,5-pregnadiene-20-one
• 英文别名: hydrocortisone enol tetraacetate；3,11β,17,21-Tetraacetoxy-pregna-3,5-dien-20-on；3,11β,17α,21-tetraacetoxypregna-3,5-dien-20-one；[2-oxo-2-[(8S,9S,10R,11S,13S,14S,17R)-3,11,17-triacetyloxy-10,13-dimethyl-1,2,7,8,9,11,12,14,15,16-decahydrocyclopenta[a]phenanthren-17-yl]ethyl] acetate
• CAS: 991-08-2
• 化学式: C₂₉H₃₈O₉
• 分子量: 530.615
• InChiKey: BWUFXFKKGSUGOE-NXQLAQFUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  38
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  122
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  3,11β,17α,21-tetraacetoxy-3,5-pregnadiene-20-one 生成 [2-[(6R,8S,9S,10R,11S,13S,14S,17R)-11,17-diacetyloxy-6-fluoro-10,13-dimethyl-3-oxo-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-yl]-2-oxoethyl] acetate
  参考文献：
  名称：

  TAKAXARA, TAKAO;SIMOKAVA, KADZUXIRO

  摘要：

  DOI：
• 作为产物：
  描述：

  醋酸氢化可的松 、 乙酰氯 生成 3,11β,17α,21-tetraacetoxy-3,5-pregnadiene-20-one
  参考文献：
  名称：

  Schmitt,J. et al., Bulletin de la Societe Chimique de France, 1964, p. 2768 - 2778

  摘要：

  DOI：

文献信息

• Microwave induced selective enolization of steroidal ketones and efficient acetylation of sterols in semisolid state
  作者：Padma Marwah、Ashok Marwah、Henry A. Lardy

  DOI：10.1016/s0040-4020(03)00207-2

  日期：2003.3

  Under microwave irradiation steroidal enones, more specifically, position three carbonyls were efficiently and selectively converted to the corresponding enol acetates in the presence of additional enolizable carbonyl functions at other positions, using acetic anhydride and a catalytic amount of toluene-p-sulfonic acid. Acetylation of hydroxyl groups of the sterols, including those at the hindered

  在微波辐射下，更具体地，使用乙酸酐和催化量的甲苯-对磺酸，在其他位置存在另外的可烯丙基的羰基官能团的情况下，在其他位置上，将三个位置的羰基化合物有效且选择性地转化为相应的烯醇乙酸酯。固醇的羟基的乙酰化，包括在受阻位置的羟基，几乎是定量的。严格的无水条件不是乙酰化的前提条件，反应系统很容易耐受高达10％（v / v）的水分。
• Kinetics of Electrophilic Fluorination of Steroids and Epimerisation of Fluorosteroids
  作者：Neshat Rozatian、Antal Harsanyi、Ben J. Murray、Alexander S. Hampton、Emily J. Chin、Alexander S. Cook、David R. W. Hodgson、Graham Sandford

  DOI：10.1002/chem.202001120

  日期：2020.9.16

  synthesised by electrophilic fluorination, form a significant proportion of marketed pharmaceuticals. To gain quantitative information on fluorination at the 6‐position of steroids, kinetics studies were conducted on enol ester derivatives of progesterone, testosterone, cholestenone and hydrocortisone with a series of electrophilic N−F reagents. The stereoselectivities of fluorination reactions of progesterone

  通过亲电氟化合成的氟化类固醇在市售药物中占有很大比例。为了获得类固醇6位氟化的定量信息，使用一系列亲电子NF试剂对孕酮、睾酮、胆固醇和氢化可的松的烯醇酯衍生物进行了动力学研究。研究了孕酮烯醇乙酸酯氟化反应的立体选择性以及甲醇和水等添加剂的动力学效应。详细介绍了 6β-氟孕酮在 HCl/乙酸溶液中差向异构化为药理活性更强的 6α-氟孕酮异构体的动力学。
• Site-selective fluorination of organic compounds using 1-alkyl-4-fluoro-1,4-diazabicyclo[2.2.2]octane salts (selectfluor reagents)
  作者：G. Sankar Lal

  DOI：10.1021/jo00062a023

  日期：1993.5

  The new ''N-F''-type electrophilic reagent family of 1-alkyl-4-fluoro-1,4-diazabicyclo[2.2.2]octane salts8d (derived from elemental fluorine (F2) and 1-alkyl-1,4-diazabicyclo[2.2.2]octane salts) has been found to be very effective for the fluorination of a wide variety of organic substrates. These include steroidal enol acetates and silyl enol ethers, phenyl-substituted olefins, sulfides bearing alpha-H atoms, certain carbanions, and mildly activated aromatic compounds. The products were obtained with good yields and regioselectivity under very mild reaction conditions.
• Lipase-catalyzed regioselective preparation of fatty acid esters of hydrocortisone
  作者：Paula G. Quintana、Alicia Baldessari

  DOI：10.1016/j.steroids.2009.07.010

  日期：2009.11

  A series of fatty acid derivatives of hydrocortisone has been prepared by an enzymatic methodology. Nine 21-monoacyl products and one 3,11,17-triacetyl derivative, nine of them novel compounds, were obtained in a highly regioselective way through lipase-catalyzed esterification, transesterification and alcoholysis reactions. The influence of various reaction parameters Such as acylating agent: substrate ratio, enzyme: substrate ratio. solvent, temperature and nature of acylating agent and alcohol was evaluated. Among the tested lipases. Candida antarctica lipase appeared to be the most appropriate and showed a high efficient behavior especially in a one-pot transesterification. The advantages presented by this methodology, such as mild reaction conditions and low environmental impact, make the biocatalysis a convenient way to prepare acyl derivatives of hydrocortisone. These lipophilic compounds are potential products in the pharmaceutical industry. (C) 2009 Elsevier Inc. All rights reserved.