17-iodo-4-aza-4-methyl-androst-16-en-3-one | 158136-73-3

• 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-4-aza-4-methyl-androst-16-en-3-one
• 英文别名: 17-iodo-4-methyl-4-aza-5α-androst-16-en-3-one；(3aS,3bR,5aR,9aR,9bS,11aS)-1-iodo-6,9a,11a-trimethyl-3a,3b,4,5,5a,8,9,9b,10,11-decahydro-3H-indeno[5,4-f]quinolin-7-one
• CAS: 158136-73-3
• 化学式: C₁₉H₂₈INO
• 分子量: 413.342
• InChiKey: WNESZHJHOJBPGS-LEUWAPGVSA-N

物化性质

• 沸点：
  466.8±45.0 °C(Predicted)
• 密度：
  1.44±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  22
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  17-iodo-4-aza-4-methyl-androst-16-en-3-one 在 四(三苯基膦)钯 作用下， 以 甲苯 为溶剂， 反应 14.0h， 生成 1',2'-bis(ethoxycarbonyl)(4-aza-methylandrostano)[16α,17-c]-1',2',3',6'-tetrahydro-1',2'-pyridazine
  参考文献：
  名称：

  一锅法斯蒂尔偶联和杂-狄尔斯-阿尔德反应简便合成甾体[16,17-c]四氢哒嗪衍生物

  摘要：

  作为 16a-和 16β-异构体的混合物的新型甾体 [16,17-c]四氢哒嗪衍生物的合成已通过连续的 Stille 偶联和杂-Diels-Alder 反应完成。产物在一锅反应中获得，无需分离二烯中间体。

  DOI：

  10.1055/s-2006-942517

文献信息

• Facile Synthesis of Steroidal Primary Amides via Palladium-Catalyzed Aminocarbonylation of Steroidal Alkenyl Halides
  作者：Rita Skoda-Földes、János Balogh、Sándor Mahó、Viktor Háda、László Kollár

  DOI：10.1055/s-2008-1067265

  日期：2008.10

  A new method for the synthesis of primary amides from alkenyl iodides in one carbonylation step using ammonium carbamate as ammonia synthon is reported. The products were obtained in good yields under mild reaction conditions using CO (1-6 bar). Steroidal substrates with various moieties (e.g., 6-OH group, lactams, or aromatic A-ring) could be converted selectively into the products.

  报道了一种使用氨基甲酸铵作为氨合成子在羰基化步骤中由链烯基碘合成伯酰胺的新方法。使用 CO (1-6 bar) 在温和的反应条件下以良好的收率获得产物。具有各种部分（例如，6-OH 基团、内酰胺或芳族 A 环）的甾体底物可以选择性地转化为产物。
• Facile, high-yielding synthesis of steroidal hydrazides via homogeneous hydrazinocarbonylation reaction
  作者：László Kollár、Zsolt Szarka、Judit Horváth、Zoltán Tuba

  DOI：10.1016/s0040-4039(97)00903-9

  日期：1997.6

  17-(N-(phenylamino)-carbamoyl)-androst-16-enes were synthesised in high yields in palladium-catalysed hydrazinocarbonylation of the corresponding 17-iodoandrost-16-ene derivatives under mild reaction conditions. (C) 1997 Elsevier Science Ltd.
• Synthesis of steroid–ferrocene conjugates of steroidal 17-carboxamides via a palladium-catalyzed aminocarbonylation – Copper-catalyzed azide–alkyne cycloaddition reaction sequence
  作者：Eszter Szánti-Pintér、János Balogh、Zsolt Csók、László Kollár、Ágnes Gömöry、Rita Skoda-Földes

  DOI：10.1016/j.steroids.2011.07.006

  日期：2011.11

  Steroids with the 17-iodo-16-ene functionality were converted to ferrocene labeled steroidal 17-carboxamides via a two step reaction sequence. The first step involved the palladium-catalyzed aminocarbonylation of the alkenyl iodides with prop-2-yn-1-amine as the nucleophile in the presence of the Pd(OAc)(2)/ PPh(3) catalyst system. In the second step, the product N-(prop-2-ynyl)-carboxamides underwent a facile azide-alkyne cycloaddition with ferrocenyl azides in the presence of CuSO(4)/sodium ascorbate to produce the steroid ferrocene conjugates. The new compounds were obtained in good yield and were characterized by (1)H and (13)C NMR, IR. MS and elemental analysis. (C) 2011 Elsevier Inc. All rights reserved.
• Microwave-assisted Stille-coupling of steroidal substrates
  作者：Rita Skoda-Földes、Péter Pfeiffer、Judit Horváth、Zoltán Tuba、László Kollár

  DOI：10.1016/s0039-128x(02)00026-0

  日期：2002.7

  Steroidal dienes were synthesised by Stille-coupling of the corresponding alkenyl iodides with vinyltributyltin under microwave irradiation in a domestic microwave oven in drastically reduced reaction times. Rate acceleration was observed also in the one-pot Stille-coupling-Diels-Alder reaction of 17-iodo-5alpha-androst-16-ene. Stereoselectivity of cycloaddition was slightly improved with diethyl maleate as the dienophile, compared to that achieved with thermal heating. (C) 2002 Elsevier Science Inc. All rights reserved.
• Heck reactions of steroidal alkenyl iodides
  作者：Rita Skoda-Földes、Marianna Bodnár、László Kollár、Judit Horváth、Zoltán Tuba

  DOI：10.1016/s0039-128x(97)00140-2

  日期：1998.2

  Heck reactions of some steroid derivatives possessing iodo-alkenyl moiety (17-iodo-androst-16-ene, 1, 17-iodo-4-aza-4-methyl-androst-16-en-3-one, 2, 17-iodo-4-aza-androst-16-en-3-one, 3) were carried out in the presence of palladium catalysts using various olefins (methyl acrylate, ethyl methacrylate, allyl alcohol and allyl acetate) as coupling partners. With methyl acrylate, a side reaction was observed: the coupling product underwent a Diels-Alder reaction with the excess of methyl acrylate resulting in a six-membered carbocyclic E-ring. Reaction conditions of the synthesis of the Heck-product were optimized. Although the coupling with allyl alcohol led to the formation of 21-formyl-16-pregnene derivatives, the synthesis of the corresponding steroidal unsaturated alcohol could be achieved only via hydrolysis of the coupling product of the alkenyl iodide with allyl acetate. (C) 1998 by Elsevier Science Inc.