17-iodo-androst-16-ene | 26313-26-8

• 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: 17-iodo-androst-16-ene
• 英文别名: 17-iodo-5α-androst-16-ene；17-Iodo-5alpha-androst-16-ene；(5R,8R,9S,10S,13S,14S)-17-iodo-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15-dodecahydro-1H-cyclopenta[a]phenanthrene
• CAS: 26313-26-8
• 化学式: C₁₉H₂₉I
• 分子量: 384.344
• InChiKey: GRWGYUOEHBHMFM-HKQXQEGQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  20
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  17-iodo-androst-16-ene 在 tris(dibenzylideneacetone)dipalladium(0) chloroform complex 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 14.0h， 以60%的产率得到16-(androst-16'-en-17'-yl)androst-16-ene
  参考文献：
  名称：

  Homogeneous catalytic dehalodimerization of 17-iodo-Δ16 steroids

  摘要：

  17-Iodo-Delta(16) steroids undergo selective dimerization and carbonylative dimerization in the presence of palladium catalysts in dimethylformamide which result in 16-17'-coupled dienes and 17-carboxylic anhydrides, respectively. Moderate to good yields have been obtained for both types of dimers.

  DOI：

  10.1016/0039-128x(95)00120-f
• 作为产物：
  描述：

  5α-Androstan-17-on-hydrazon 在 碘 作用下， 生成 17-iodo-androst-16-ene
  参考文献：
  名称：

  氨基羰基化反应合成N-吡啶甲基羧酰胺

  摘要：

  在2-，3-和4-吡啶甲基胺以及具有1-吡啶甲基取代基的仲胺存在下，进行钯催化的碘樟脑和甾体碘代烯烃的氨基羰基化。通常，伯甲基吡啶胺需要少于2小时才能实现几乎完全的转化。仲胺被证明反应性较低，需要6-24小时，具体取决于底物结构。分离出相应的羧酰胺，产率中等至优异。α，β-不饱和羧酰​​胺的合成是基于由可烯醇化的酮合成碘代烯烃底物。

  DOI：

  10.1016/j.tet.2021.132128

文献信息

• Facile Synthesis of Steroidal Phenyl Ketones via Homogeneous Catalytic Carbonylation
  作者：Rita Skoda-Földes、Zoltán Székvölgyi、László Kollár、Zoltán Berente、Judit Horváth、Zoltán Tuba

  DOI：10.1016/s0040-4020(00)00241-6

  日期：2000.5

  Steroidal phenyl ketones were synthesised in high yields by palladium-catalysed carbonylation reactions of 17-iodo-androst-16-ene derivatives in the presence of NaBPh4 under mild reaction conditions. Alkenyl bromides or enol triflates gave lower yields in the same reaction.

  在温和的反应条件下，在NaBPh 4的存在下，钯催化的17-碘-雄烷-16-烯衍生物的羰基化反应可高产率地合成甾族苯基酮。在同一反应中，烯基溴化物或烯醇三氟甲磺酸酯的收率较低。
• Hydroxy-steroids. Part XVIII. Reactions of 17β-chloro-16α,17α-epoxy-5α-androstane and the preparation of 17β-iodo-16α,17α-epoxy-5α-androstane
  作者：W. A. Denny、V. Kumar、G. D. Meakins、J. Pragnell、J. Wicha

  DOI：10.1039/p19720000486

  日期：——

  17β-Chloro- and 17β-iodo-16α,17α-epoxy-5α-androstane are reactive compounds which undergo ready rearrangement into 16-halogeno-17-ketones. On treatment with aluminium chloride the chloro-epoxide undergoes methyl group migration, to give 17-methyl-18-nor-5α-androst-13(17)-en-16-one in 82% yield. The iodo-epoxide, which is unstable, is best obtained (22% yield) by oxidising 17-iodo-5α-androst-16-ene

  17β-氯-和17β-碘-16α，17α-环氧-5α-雄甾烷是反应性化合物，它们容易重新排列为16-卤素-17-酮。用氯化铝处理后，氯代环氧化合物发生甲基迁移，以82％的收率得到17-甲基-18-nor-5α-androst-13（17）-en-16-one。通过在苯中用过氧月桂酸氧化17-碘5α-雄甾16-烯可以最好地获得不稳定的碘化环氧化物（22％的收率）。
• Amino- and azidocarbonylation of iodoalkenes
  作者：Gábor Mikle、Rita Skoda-Földes、László Kollár

  DOI：10.1016/j.tet.2021.132495

  日期：2021.11

  on the structure of the acyl azides, consecutive hydrolysis toward corresponding primary amides was observed. ‘Direct’ aminocarbonylation of the same iodoalkenes was also carried out by using ammonium carbamate as ammonia source under mild conditions. The α,β-unsaturated primary amides, formed in a chemoselective reaction, were isolated in good to excellent yields.

  碘代烯烃可通过其腙从酮中获得，经过钯催化的叠氮羰基化。根据酰基叠氮化物的结构，观察到连续水解为相应的伯酰胺。在温和条件下，使用氨基甲酸铵作为氨源也可以进行相同碘代烯烃的“直接”氨基羰基化。在化学选择性反应中形成的 α,β-不饱和伯酰胺以良好至极好的产率分离。
• Alkoxycarbonylpiperidines as N-nucleophiles in the palladium-catalyzed aminocarbonylation
  作者：Attila Takács、Zsuzsanna Kabak-Solt、Gábor Mikle、László Kollár

  DOI：10.1007/s00706-014-1254-1

  日期：2014.9

  4-(ethoxycarbonyl)piperidine (ethyl isonipecotate), were used as N-nucleophiles in palladium-catalyzed aminocarbonylation of iodobenzene and iodoalkenes such as 1-iodocyclohexene and 17-iodoandrost-16-ene. While the aminocarbonylation of both iodoalkenes, carried out under mild reaction conditions, resulted in the exclusive formation of the carboxamide, the same reaction of iodobenzene brought about the mixture of

  摘要带有酯官能团的哌啶，例如2-（甲氧基羰基）哌啶（哌嗪酸甲酯），3-（乙氧基羰基）哌啶（邻苯甲酸乙酯）和4-（乙氧基羰基）哌啶（异戊烯酸乙酯），在钯-钯中用作N-亲核试剂。催化碘代苯和碘代烯烃（如1-碘代环己烯和17-碘代芳烃-16-烯）的氨基羰基化反应。尽管两种碘代烯烃的氨基羰基化在温和的反应条件下进行，导致羧酰胺的排他性形成，但是碘代苯的相同反应产生了相应的羧酰胺和2-酮羧酰胺的混合物。通过使用高一氧化碳压力（最高40 bar），通过羰基双插入形成的对后一种化合物的化学选择性大大提高。 图形概要
• Palladium catalyzed carbonylations of alkenyl halides with formic acid to get corresponding α,β-unsaturated carboxylic acids and esters
  作者：Brigitta Bartal、Gábor Mikle、László Kollár、Péter Pongrácz

  DOI：10.1016/j.mcat.2018.12.026

  日期：2019.4

  Palladium-catalysed carbonylation reactions have been developed in the presence of formic acid as carbon monoxide source. α,β-Unsaturated carboxylic acids and esters were synthesized by the transformation of alkenyl halides in moderate to good yields. The selection of the base proved to be crucial regarding the reaction outcome. A set of various substrates were proven under optimised reaction conditions

  在甲酸作为一氧化碳源的情况下，已经开发了钯催化的羰基化反应。α，β-不饱和羧酸和酯是通过链烯基卤化物以中等到良好的产率合成的。事实证明，选择碱对于反应结果至关重要。在优化的反应条件下证明了一组各种底物。与脂族醇相比，酚作为O-亲核试剂表现出出色的反应性。