3,24-bis(6-chloropyridin-2-yloxy)-3α,5β-cholane | 1185506-80-2

• 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: 3,24-bis(6-chloropyridin-2-yloxy)-3α,5β-cholane
• 英文别名: (3β,5β)-3,24-bis(6-chloropyridin-2-yloxy)cholane；(3beta,5beta)-3,24-Bis(6-chloropyridin-2-yloxy)cholane；2-chloro-6-[(4R)-4-[(3S,5R,8R,9S,10S,13R,14S,17R)-3-(6-chloropyridin-2-yl)oxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentoxy]pyridine
• CAS: 1185506-80-2
• 化学式: C₃₄H₄₆Cl₂N₂O₂
• 分子量: 585.657
• InChiKey: TZJFYUDRZBKKHN-YUVCUXCQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.6
• 重原子数：
  40
• 可旋转键数：
  8
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  44.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3,24-bis(6-chloropyridin-2-yloxy)-3α,5β-cholane 、 1,3-金刚烷二乙胺 在 R-(+)-1,1'-联萘-2,2'-双二苯膦 、 bis(dibenzylideneacetone)-palladium⁽⁰⁾ 、 sodium t-butanolate 作用下， 以 1,4-二氧六环 为溶剂， 反应 15.0h， 以15%的产率得到
  参考文献：
  名称：

  Synthesis of nitrogen- and oxygen-containing macrocycles by palladium-catalyzed amination of 3,24-bis(6-chloropyridin-2-yloxy)cholane

  摘要：

  3,24-Bis(6-chloropyrdin-2-yloxy)cholane prepared from cholane-3,24-diol by the Mitsunobu reaction was successfully used to synthesize various polyaza macrocycles via palladium-catalyzed amination with linear polyamines. The contribution of side formation of cyclic oligomers was found to depend on the polyamine nature.

  DOI：

  10.1134/s1070428009010114
• 作为产物：
  描述：

  6-氯吡啶-2-醇 、 5β-cholane-3α,24-diol 在 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 24.0h， 以85%的产率得到3,24-bis(6-chloropyridin-2-yloxy)-3α,5β-cholane
  参考文献：
  名称：

  Synthesis of nitrogen- and oxygen-containing macrocycles by palladium-catalyzed amination of 3,24-bis(6-chloropyridin-2-yloxy)cholane

  摘要：

  3,24-Bis(6-chloropyrdin-2-yloxy)cholane prepared from cholane-3,24-diol by the Mitsunobu reaction was successfully used to synthesize various polyaza macrocycles via palladium-catalyzed amination with linear polyamines. The contribution of side formation of cyclic oligomers was found to depend on the polyamine nature.

  DOI：

  10.1134/s1070428009010114

文献信息

• Palladium-catalyzed amination in the synthesis and modification of acyclic oxadiamino cholane derivatives
  作者：E. R. Ranyuk、A. D. Averin、N. V. Lukashev、A. K. Buryak、I. P. Beletskaya

  DOI：10.1134/s1070428009120021

  日期：2009.12

  Palladium-catalyzed reactions of 24-(haloaryloxy)cholanes and 3,24-bis(haloaryloxy)cholanes with excess oxadiamines gave the corresponding mono- and bis(oxadiamino)-substituted cholanes which were subjected to palladium-catalyzed arylation with 1,3-dibromobenzene, 2,6-dibromopyridine, 1,8-dichloroanthracene, 9-bromoanthracene, 1-chloroanthracene, and 1-chloroanthraquinone. The results of these reactions were found to strongly depend on the haloarene nature. The arylation with 1,3-dibromobenzene and 2,6-dibromopyridine led to the formation of new macrocyclic compounds containing one cholane, one arene, and two oxadiamine fragments.