1',4',16,17-tetrahydro-3β-acetoxy-6'-bromo-4'-methyl-(16β,17α)-androsta-5,16-dieno[17,16-b]quinoline | 773876-33-8

• 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: 1',4',16,17-tetrahydro-3β-acetoxy-6'-bromo-4'-methyl-(16β,17α)-androsta-5,16-dieno[17,16-b]quinoline
• 英文别名: [(1S,2S,7S,10R,11S,14S,15R,16S,24R)-19-bromo-10,14,16-trimethyl-23-azahexacyclo[12.11.0.02,11.05,10.015,24.017,22]pentacosa-4,17(22),18,20-tetraen-7-yl] acetate
• CAS: 773876-33-8
• 化学式: C₂₉H₃₈BrNO₂
• 分子量: 512.53
• InChiKey: PUPIOTBBTWHKEZ-KQDNBWGHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.4
• 重原子数：
  33
• 可旋转键数：
  2
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1',4',16,17-tetrahydro-3β-acetoxy-6'-bromo-4'-methyl-(16β,17α)-androsta-5,16-dieno[17,16-b]quinoline 在 sodium methylate 、 potassium acetate 作用下， 以 甲醇 为溶剂， 生成 1',4',16,17-tetrahydro-3β-hydroxy-1'-acetyl-6'-bromo-4'-methyl-(16β,17α)-androsta-5,16-dieno[17,16-b]quinoline
  参考文献：
  名称：

  Synthesis of novel steroid-tetrahydroquinoline hybrid molecules and d-homosteroids by intramolecular cyclization reactions

  摘要：

  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.

  DOI：

  10.1016/j.steroids.2004.01.004
• 作为产物：
  描述：

  4-溴苯胺 、 trans-3β-acetoxy-16,17-seco-pregna-5,17(20)-dien-16-al 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 以77%的产率得到1',4',16,17-tetrahydro-3β-acetoxy-6'-bromo-4'-methyl-(16β,17α)-androsta-5,16-dieno[17,16-b]quinoline
  参考文献：
  名称：

  Synthesis of novel steroid-tetrahydroquinoline hybrid molecules and d-homosteroids by intramolecular cyclization reactions

  摘要：

  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.

  DOI：

  10.1016/j.steroids.2004.01.004