3-methylidenespiro[cyclobutane-1,3'-(5'α)-cholestane] | 1422258-13-6

• 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-methylidenespiro[cyclobutane-1,3'-(5'α)-cholestane]
• 英文别名: 3'-methylene-spiro[(5α)-cholestane-3,10-cyclobutane]；(5S,8R,9S,10S,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-3'-methylidenespiro[1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthrene-3,1'-cyclobutane]
• CAS: 1422258-13-6
• 化学式: C₃₁H₅₂
• 分子量: 424.754
• InChiKey: VLFPJKXAVWEKNU-YJJGUQQZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.4
• 重原子数：
  31
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.94
• 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：

  3-methylidenespiro[cyclobutane-1,3'-(5'α)-cholestane] 在 吡啶 、 二氯二茂锆 、 三氟化硼乙醚 、 对甲苯磺酰氯 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 36.0h， 生成 dispiro[tetrahygrofuran-3",3'-cyclobutane-1',3-(5α)-cholestane]
  参考文献：
  名称：

  Catalytic cycloalumination in steroid chemistry: The introduction of a spirotetrahydrofuran or spirotetrahydroselenophene moiety into a 3′-methylene-(5α)-spirocholestane-3,1′-cyclobutane molecule

  摘要：

  Cycloalumination of 3'-methylene-(5 alpha)-spirocholestane-3,1'-cyclobutane with triethylaluminum catalyzed by Cp2ZrCl2 was accomplished for the first time to give (5 alpha)-spirocholestane-3,1'-(6'-ethyl-6'-aluminaspiro [3.4] octane) in 89%. The latter, without isolation, was converted into spirotetrahydroselenophene or spirotetrahydrofuran. (C) 2012 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2012.11.012
• 作为产物：
  描述：

  (5α)-Spiro-3'-one 、 亚甲基三苯基膦烷 以 二甲基亚砜 、 苯 为溶剂， 以74%的产率得到3-methylidenespiro[cyclobutane-1,3'-(5'α)-cholestane]
  参考文献：
  名称：

  Synthesis and transformations of metallacycles 42. Cp2ZrCl2-Catalyzed cycloalumination of 3-methylidenespiro[cyclobutane-1,3′-(5′α)-cholestane] with Et3Al

  摘要：

  在Cp2ZrCl2催化下，3-亚甲基螺[环丁烷-1,3′-(5′α)-胆甾烷]与Et3Al发生环铝化反应，以84%的收率得到3-乙基-3-铝双螺[环戊烷-1,1′-环丁烷-3′,3″-(5″α)-胆甾烷]。

  DOI：

  10.1007/s11172-013-0027-z

文献信息

• Synthesis and transformations of metallacycles 42. Cp2ZrCl2-Catalyzed cycloalumination of 3-methylidenespiro[cyclobutane-1,3′-(5′α)-cholestane] with Et3Al
  作者：U. M. Dzhemilev、R. A. Tuktarova、I. I. Islamov、L. M. Khalilov、Z. A. Starikova、V. A. D’yakonov

  DOI：10.1007/s11172-013-0027-z

  日期：2013.1

  A Cp2ZrCl2-catalyzed cycloalumination of 3-methylidenespiro[cyclobutane-1,3′-(5′α)-cholestane] with Et3Al gives 3-ethyl-3-aluminadispiro[cyclopentane-1,1′-cyclobutane-3′,3″-(5″α)-cholestane] in 84% yield.

  在Cp2ZrCl2催化下，3-亚甲基螺[环丁烷-1,3′-(5′α)-胆甾烷]与Et3Al发生环铝化反应，以84%的收率得到3-乙基-3-铝双螺[环戊烷-1,1′-环丁烷-3′,3″-(5″α)-胆甾烷]。
• Catalytic cycloalumination in steroid chemistry: The introduction of a spirotetrahydrofuran or spirotetrahydroselenophene moiety into a 3′-methylene-(5α)-spirocholestane-3,1′-cyclobutane molecule
  作者：Vladimir A. D’yakonov、Regina A. Tuktarova、Ilgiz I. Islamov、Leonard M. Khalilov、Usein M. Dzhemilev

  DOI：10.1016/j.steroids.2012.11.012

  日期：2013.2

  Cycloalumination of 3'-methylene-(5 alpha)-spirocholestane-3,1'-cyclobutane with triethylaluminum catalyzed by Cp2ZrCl2 was accomplished for the first time to give (5 alpha)-spirocholestane-3,1'-(6'-ethyl-6'-aluminaspiro [3.4] octane) in 89%. The latter, without isolation, was converted into spirotetrahydroselenophene or spirotetrahydrofuran. (C) 2012 Elsevier Inc. All rights reserved.