17-bromo-androsta-2,16-diene | 62684-13-3

• 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-bromo-androsta-2,16-diene
• 英文别名: (5S,8R,9S,10S,13S,14S)-17-bromo-10,13-dimethyl-4,5,6,7,8,9,11,12,14,15-decahydro-1H-cyclopenta[a]phenanthrene
• CAS: 62684-13-3
• 化学式: C₁₉H₂₇Br
• 分子量: 335.327
• InChiKey: AHQKTWMYUNYJIW-HKQXQEGQSA-N

物化性质

• 沸点：
  380.8±42.0 °C(Predicted)
• 密度：
  1.227±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  20
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.79
• 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-bromo-androsta-2,16-diene 在 间氯过氧苯甲酸 作用下， 以 氯仿 、 乙腈 为溶剂， 反应 48.0h， 生成 2α,3α-epoxy-17-oxo-16β-(4'-methyl-1'-piperazino)-5α-androstane
  参考文献：
  名称：

  Tuba, Arzneimittel-Forschung/Drug Research, 1980, vol. 30, # 2 A, p. 342 - 346

  摘要：

  DOI：
• 作为产物：
  描述：

  5alpha-雄甾-2-烯-17-酮 在 N-溴代丁二酰亚胺(NBS) 、 一水合肼 、 三乙胺 作用下， 以 吡啶 、 乙醇 为溶剂， 反应 2.0h， 生成 17-bromo-androsta-2,16-diene
  参考文献：
  名称：

  Tuba, Arzneimittel-Forschung/Drug Research, 1980, vol. 30, # 2 A, p. 342 - 346

  摘要：

  DOI：

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。
• Acylated diepoxy-androstane and a process for the preparation thereof
  申请人：Richter Gedeon Vegyeszeti Gyar Rt

  公开号：US04110326A1

  公开（公告）日：1978-08-29

  A compound of the formula (I) ##STR1## wherein X is a halogen, Z.sub.1 and Z.sub.2 are both hydrogen, or Z.sub.1 is hydroxy and Z.sub.2 is chlorine, or Z.sub.1 and Z.sub.2 together stand for an .alpha.-epoxy group.

  化学式(I)的化合物##STR1##其中X是卤素，Z.sub.1和Z.sub.2都是氢，或者Z.sub.1是羟基而Z.sub.2是氯，或者Z.sub.1和Z.sub.2一起代表一个α-环氧基团。
• 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.
• Palladium-catalyzed homogeneous coupling reactions of steroids with organostannanes
  作者：Rita Skoda-Földes、Zita Csákai、Lászlo Kollár、Judit Horváth、Zoltán Tuba

  DOI：10.1016/0039-128x(95)00146-h

  日期：1995.12

  Direct and carbonylative coupling reactions of various steroid derivatives possessing iodo- and bromo-alkenyl moiety (17-iodo-androst-16-ene, 1, 17-bromoandrost-2, 16-diene, 2, 17-iodo-4-aza-4-methylandrost-16-en-3-one, 3, 17-iodo-4-azaandrost-16-en-3-one, 4) with vinyltributylstannane and ethynyltributylstannane were carried out in the presence of various palladium catalysts. While carbonylation took place only with vinyltributylstannane, 17-vinyl-, and 17-ethynyl-Delta(16) steroids were produced via direct coupling with vinyltributylstannane and ethynyltributylstannane, respectively. Activities of some catalysts based on Pd(0) and Pd(II) precursors were compared, and Pd(PPh(3))(4) was found to be superior to other complexes in most cases. In the coupling of 17-iodoandrost-16-ene with organostannanes Pd-2(dba)(3) + 8 AsPh(3) in situ catalyst was found to be even more effective.
• 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.