3β-acetoxy-17β-pivaloylandrost-5-ene-19-ol | 67192-85-2

• 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: 3β-acetoxy-17β-pivaloylandrost-5-ene-19-ol
• 英文别名: [(3S,8R,9S,10S,13S,14S,17S)-3-acetyloxy-10-(hydroxymethyl)-13-methyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl] 2,2-dimethylpropanoate
• CAS: 67192-85-2
• 化学式: C₂₆H₄₀O₅
• 分子量: 432.601
• InChiKey: NCQPRLGHTOPUDO-JZRTWBLVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  31
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3β-acetoxy-17β-pivaloylandrost-5-ene-19-ol 在 sodium iodide 作用下， 以 异丙醇 为溶剂， 生成 2,2-Dimethyl-propionic acid (3S,8S,9S,10S,13S,14S,17S)-3-acetoxy-10-iodomethyl-13-methyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl ester
  参考文献：
  名称：

  19-碘-5-雄烯衍生物的过酸氧化中的烯丙基重排

  摘要：

  在醚中甾体均烯丙基碘的1-3-氯过苯甲酸氧化后，生成的产物2a，2b和4由高度不稳定的高价碘中间体产生。

  DOI：

  10.1016/s0040-4039(00)96826-6
• 作为产物：
  描述：

  2,2-Dimethyl-propionic acid (3S,8S,9S,10S,13S,14S,17S)-3-acetoxy-10-formyl-13-methyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl ester 在 lithium tri-t-butoxyaluminum hydride 作用下， 生成 3β-acetoxy-17β-pivaloylandrost-5-ene-19-ol
  参考文献：
  名称：

  Rodewald,W.J. et al., Polish Journal of Chemistry, 1978, vol. 52, p. 715 - 719

  摘要：

  DOI：

文献信息

• Synthesis and Photochemical Trasformations of 19-Phenylsulfonyl Provitamin D Analogue
  作者：Piotr Grzegorzewski、Izabela Koladkiewicz、Jacek W. Morzycki、Rafal R. Sicinski

  DOI：10.1135/cccc19981597

  日期：——

  The synthesis of provitamin D analogue 19-(phenylsulfonyl)androsta-5,7-diene-3β,17β-diyl 3-acetate 17-pivalate (20) has been accomplished from 19-hydroxyandrost-5-ene-3β,17β-diyl 3-acetate 17-pivalate. 19-(Phenylsulfonyl)androst-5-ene-3β,17β-diyl 3-acetate 17-pivalate (10), a precursor of 20, was first obtained in low yield in the nucleophilic displacement reactions of 19-halogenated-5-ene steroids with sodium benzenesulfinate. Then a more efficient method has been used, which involves protection of the double bond as an epoxide. Introduction of the C(7)-C(8) double bond into olefin 10 has been also achieved in two ways. The first involved bromination-dehydrobromination and the other consisted of an allylic oxidation of olefin 10 leading to enone and the Bamford-Stevens reaction of its tosylhydrazone. UV irradiation of 5,7-diene 20 resulted in formation of a complex mixture of products. The structures of five isolated compounds were established on the basis of their ¹H NMR spectra and mechanistic rationale.

  已完成合成前维生素D类似物19-(苯磺酰基)雄烯-5,7-二烯-3β,17β-二醇 3-乙酸酯 17-季戊酸酯（20）从19-羟基雄烷-5-烯-3β,17β-二醇 3-乙酸酯 17-季戊酸酯。19-(苯磺酰基)雄烷-5-烯-3β,17β-二醇 3-乙酸酯 17-季戊酸酯（10），作为20的前体，首先在19-卤代-5-烯类固醇与苯磺酸钠亲核取代反应中低收率获得。然后采用了更有效的方法，涉及将双键保护为环氧化物。将C(7)-C(8)双键引入烯烃10也有两种方法。第一种涉及溴化-脱溴化反应，另一种包括烯烃10的烯丙基氧化，导致烯酮和其对甲苯磺酰肼酮的Bamford-Stevens反应。对5,7-二烯20进行紫外辐射导致形成复杂的产物混合物。基于它们的1H核磁共振谱和机理合理性，已确定了五种分离化合物的结构。
• Synthesis and photoisomerization of provitamin D analog with 11β,19-oxide bridge
  作者：Rafal R. Siciński

  DOI：10.1139/v95-108

  日期：1995.6.1

  Triol diester 1 was converted into the B-ring 5,7-diene 6 representing the first example of the provitamin D analog where the 10β angular methyl group is connected to ring C by a C11/C19 ether linkage. Ultraviolet light irradiation of 6 resulted in the formation of stereoisomeric 9β, 10α-compound 8a. The structure of the photoproduct was established by analysis of vicinal ¹H–¹H coupling constants and by molecular mechanics. Keywords: 11β, 19-oxido steroids, lumisterol analog, 5,7-androstadienes, electrocyclic reactions, photochemistry.

  Triol二酯1被转化为B环5,7-二烯6，代表了前维生素D类似物的第一个例子，其中10β角甲基基团通过C11/C19醚键连接到环C。对6进行紫外光照射导致产生立体异构体9β, 10α-化合物8a。通过分析邻位1H-1H偶合常数和分子力学，确定了光产物的结构。关键词：11β，19-氧化类固醇，卢米斯特罗类似物，5,7-雄烯二烯，电环反应，光化学。
• Jaszczynski, Jerzy R.; Sicinski, Rafal R.; Rodewald, Wladyslaw J., Polish Journal of Chemistry, 1984, vol. 58, # 7-8-9, p. 711 - 720
  作者：Jaszczynski, Jerzy R.、Sicinski, Rafal R.、Rodewald, Wladyslaw J.

  DOI：——

  日期：——
• Rodewald,W. et al., Polish Journal of Chemistry, 1978, vol. 52, p. 501 - 509
  作者：Rodewald,W. et al.

  DOI：——

  日期：——