(10S,13R,17R)-3-ethynyl-10,13-dimethyl-17-((R)-6-methylheptan-2-yl)-4,5,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene | 1449115-49-4

• 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: (10S,13R,17R)-3-ethynyl-10,13-dimethyl-17-((R)-6-methylheptan-2-yl)-4,5,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene
• 英文别名: (5S,8R,9S,10S,13R,14S,17R)-3-ethynyl-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene
• CAS: 1449115-49-4
• 化学式: C₂₉H₄₆
• 分子量: 394.684
• InChiKey: NNMZBOMSQADIJS-AXYOXNHISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.1
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.86
• 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：

  对甲苯磺酰叠氮 、 (10S,13R,17R)-3-ethynyl-10,13-dimethyl-17-((R)-6-methylheptan-2-yl)-4,5,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene 在 噻吩-2-甲酸亚铜(I) 、 bis{rhodium[3,3'-(1,3-phenylene)bis(2,2-dimethylpropanoic acid)]} 作用下， 以 1,2-二氯乙烷 为溶剂， 以81%的产率得到(1R,10aS,12aR)-10a,12a-dimethyl-1-((R)-6-methylheptan-2-yl)-9-tosyl-1,2,3,3a,3b,4,5,5a,6,9,10,10a,10b,11,12,12a-hexadecahydrocyclopenta[5,6]naphtho[2,1-f]indole
  参考文献：
  名称：

  环酮转化为 2,3-稠合吡咯和取代吲哚

  摘要：

  已经实现了由环酮高效合成 2,3-稠合吡咯。该转化包括 4-链烯基-1-磺酰基-1,2,3-三唑的铑催化反应，具有不寻常的 4π 电环化。该方法进一步扩展到使用从 1-乙炔基环己烯开始的一锅反应合成吲哚。

  DOI：

  10.1021/ja405043g
• 作为产物：
  描述：

  5-Alpha-胆甾烷-3-酮 在 copper(l) iodide 、 四(三苯基膦)钯 、 双(三甲基硅烷基)氨基钾 、 三乙胺 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 25.0h， 生成 (10S,13R,17R)-3-ethynyl-10,13-dimethyl-17-((R)-6-methylheptan-2-yl)-4,5,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene
  参考文献：
  名称：

  One-Pot Relay Gold(I) and Brønsted Acid Catalysis: Cyclopenta[b]annulation of Indoles via Hydroamination/Nazarov-Type Cyclization Cascade of Enynols

  摘要：

  An expedient relay gold(I) and Bronsted acid catalyzed hydroamination/Nazarov cyclization of 1-(2-aminophenyl)pent-4-en-2-ynols for the synthesis of various polyfunctionalized cyclopenta[b]indoles is described. The synthetic utility of this method has been demonstrated by the synthesis of a few unprecedented pentacyclic indoles and indole steroidal hybrids. Further, the new methodology has been successfully applied to the enantioselective synthesis of core carbon structure of the polyveoline family of natural products.

  DOI：

  10.1021/acs.orglett.5b02632

文献信息

• Facile Synthesis of 2,5-Disubstituted Thiazoles from Terminal Alkynes, Sulfonyl Azides, and Thionoesters
  作者：Tomoya Miura、Yuuta Funakoshi、Yoshikazu Fujimoto、Junki Nakahashi、Masahiro Murakami

  DOI：10.1021/acs.orglett.5b00960

  日期：2015.5.15

  A sequential procedure for the synthesis of 2,5-disubstituted thiazoles from terminal alkynes, sulfonyl azides, and thionoesters is reported. A copper(I)-catalyzed 1,3-dipolar cycloaddition of terminal alkynes with sulfonyl azides affords 1-sulfonyl-1,2,3-triazoles, which then react with thionoesters in the presence of a rhodium(II) catalyst. The resulting 3-sulfonyl-4-thiazolines subsequently aromatize

  据报道从末端炔烃，磺酰基叠氮化物和硫代磺酸酯合成2，5-二取代的噻唑的顺序方法。末端炔烃与磺酰基叠氮化物的铜（I）催化的1,3-偶极环加成反应生成1-磺酰基-1,2,3-三唑，然后在铑（II）催化剂存在下与硫磺酸酯反应。随后通过消除磺酰基基团将所得的3-磺酰基-4-噻唑啉芳香化为相应的2，5-二取代的噻唑。
• Direct Production of Enaminones from Terminal Alkynes via Rhodium-Catalyzed Reaction of Formamides with <i>N</i>-Sulfonyl-1,2,3-triazoles
  作者：Tomoya Miura、Yuuta Funakoshi、Takamasa Tanaka、Masahiro Murakami

  DOI：10.1021/ol5010774

  日期：2014.5.16

  A rhodium-catalyzed reaction of formamides with N-sulfonyl-1,2,3-triazoles is developed to formulate a new one-pot procedure for the direct synthesis of a-amino enaminones from terminal alkynes.