trans-3β-acetoxy-16,17-seco-pregna-5,17(20)-dien-16-al | 649723-80-8

• 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: trans-3β-acetoxy-16,17-seco-pregna-5,17(20)-dien-16-al
• 英文别名: D-seco-pregnene aldehyde；[(2S,4aR,4bS,7R,8S,8aS)-4a,7-dimethyl-8-(2-oxoethyl)-7-[(E)-prop-1-enyl]-1,2,3,4,4b,5,6,8,8a,9-decahydrophenanthren-2-yl] acetate
• CAS: 649723-80-8
• 化学式: C₂₃H₃₄O₃
• 分子量: 358.521
• InChiKey: SYJGIMXLLJLENX-RSTBDCAISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  trans-3β-acetoxy-16,17-seco-pregna-5,17(20)-dien-16-al 在 三氟化硼乙醚 作用下， 以 甲醇 为溶剂， 反应 0.33h， 生成 (3'S,17S)-3'-methyl-2'-(4-methylphenyl)-3',4'-dihydro-2'H-pyrazolo[4',5':17,16]androst-5-ene 3β-acetate
  参考文献：
  名称：

  Stereoselective Synthesis of Novel Δ⁵-Androstenoarylpyrazoline Derivatives by BF₃·OEt₂-Induced Intramolecular 1,3-Dipolar Cycloaddition

  摘要：

  不饱和d-seco-孕甾醛的苯肼缩合物在BF3·OEt2的催化下经历了分子内1,3-偶极环加成反应，在极温和的条件下得到了新型的吡唑啉融合Δ5-雄甾烯衍生物。环闭合通过相应的亚胺中间体以优良至极佳的选择性和产率进行，并且对p-苯基取代基的电子特征表现出显著依赖性。

  DOI：

  10.1055/s-2007-977452
• 作为产物：
  描述：

  pregn-5-ene-3β,16α,20β-triol 3,16-diacetate 在 氢氧化钾 作用下， 以 吡啶 、 甲醇 为溶剂， 反应 24.08h， 生成 trans-3β-acetoxy-16,17-seco-pregna-5,17(20)-dien-16-al
  参考文献：
  名称：

  Woelfling, Janos; Magyar, Angela; Schneider, Gyula, Monatshefte fur Chemie, 2003, vol. 134, # 10, p. 1387 - 1393

  摘要：

  DOI：

文献信息

• Intramolecular approach to some new D-ring-fused steroidal isoxazolidines by 1,3-dipolar cycloaddition: synthesis, theoretical and in vitro pharmacological studies
  作者：Éva Frank、Zoltán Mucsi、Mihály Szécsi、István Zupkó、János Wölfling、Gyula Schneider

  DOI：10.1039/c0nj00150c

  日期：——

  Intramolecular 1,3-dipolar cycloaddition of alkenyl oxime 5, obtained from trans-3β-acetoxy-16,17-secopregna-5,17(20)-dien-16-al 2 with hydroxylamine hydrochloride, was carried out under reflux in toluene to furnish a ca. 3 : 2 mixture of D-ring-fused isoxazolidine diastereomers 8 and 11a both with cis D/E ring junction stereochemistry. The corresponding reaction of 5 in the presence of a catalytic

  分子内的1,3-偶极环加成 烯基肟 5，从反式-3β-乙酰氧基-16,17-secopregna-5,17（20）-dien-16-al 2用盐酸羟胺，在回流下进行 甲苯以提供一个CA。3：2 D形环熔合的混合物异恶唑烷非对映异构体8和11a均具有顺式D / E环结立体化学。在催化量的BF 3 ·OEt 2存在下，相应的5的反应在温和的条件下以提高的收率得到了单一异构体8。通过在BLYP / 6-31G（d）的理论水平上对拟议机理的计算，支持了热诱导和BF 3催化转变的实验结果。类似地，环化D-secopregnene醛 2用ñ取代的 羟胺衍生物（10b-e）在热条件下通过相应的烯基硝酮7b-e非对映选择性地提供了N-官能化的异恶唑烷11b -e。3-脱乙酰化合物（活动9，图12B-E ）进行了测试在体外对大鼠睾丸Ç 17,20 -裂解酶：放射性配体孵育测定显示9所施加的适度的酶抑制作用（IC
• Efficient Approach to Androstene-Fused Arylpyrazolines as Potent Antiproliferative Agents. Experimental and Theoretical Studies of Substituent Effects on BF₃-Catalyzed Intramolecular [3 + 2] Cycloadditions of Olefinic Phenylhydrazones
  作者：Éva Frank、Zoltán Mucsi、István Zupkó、Borbála Réthy、George Falkay、Gyula Schneider、János Wölfling

  DOI：10.1021/ja808636e

  日期：2009.3.25

  Highly diastereoselective Lewis acid induced intramolecular 1,3-dipolar cycloadditions of alkenyl phenylhydrazones (containing various substituents on the aromatic ring) obtained from a D-secopregnene aldehyde were carried out under fairly mild conditions to furnish androst-5-ene-fused arylpyrazolines in good to excellent yields. The ability of phenylhydrazones to undergo cyclization was found to be affected significantly by the electronic features of the substituents on the aromatic moiety. The rates of the ring-closure reactions were observed to be increased by electron-donating and decreased by electron-withdrawing groups. The experimental findings on the BF3-catalyzed transformations were supported by calculations of the proposed mechanism at the BLYP/6-31G(d) level of theory, indicating a noteworthy dependence, mainly of the initial complexation step, and hence of the whole process, on the character of the substituent. The cycloaddition was estimated to occur via a zwitterionic intermediate rather than involving a pure concerted mechanism. The antiproliferative activities of the structurally related pyrazoline derivatives were tested in vitro on three malignant human cell lines (HeLa, MCF7, and A431): the microculture tetrazolium assay revealed that several compounds exerted marked cell growth-inhibitory effects. The highest cytotoxic activities, displayed by the p-methoxyphenylpyrazoline derivative 7d (IC50 values: 2.01, 2.16, and 1.41 mu M on HeLa, MCF7, and A341 cells, respectively), were better than those of cisplatin (IC50 values: 12.43, 9.63, and 2.84 mu M, respectively).
• Synthesis of novel steroid-tetrahydroquinoline hybrid molecules and d-homosteroids by intramolecular cyclization reactions
  作者：Angéla Magyar、János Wölfling、Melanie Kubas、Jose Antonio Cuesta Seijo、Madhumati Sevvana、Regine Herbst-Irmer、Péter Forgó、Gyula Schneider

  DOI：10.1016/j.steroids.2004.01.004

  日期：2004.5

  Steroidal aryliminium salts were prepared from D-seco-pregnene aldehyde 2b, and their BF3.OEt2-catalyzed reactions were studied. The nature of the substituent R-1 in the anilines 3-6 essentially influenced the chemoselectivity. Using unsubstituted 3, 4-methoxy- (4) or 4-bromoaniline (5), different tetrahydroquinoline derivatives 7a-13a via intramolecular hetero Diels-Alder reaction were formed. In the case of 4-nitroaniline (6) the N-arylamino-D-homopregnane (14a) were also obtained. We assume, that an intramolecular Prins reaction led to this type of fluoro-D-homosteroid. The main products represent a new class of tetrahydroquinolino-androstenes. (C) 2004 Elsevier Inc. All rights reserved.