(8'R,9'S,13'S,14'S,17'S)-carbonic acid 3-(17'-hydroxy-3'-methoxy-13'-methyl-7',8',9',11',12',13',14',15',16',17'-decahydro-6H-cyclopenta[a]phenanthren-17'-yl)-prop-2-ynyl ester methyl ester | 530158-36-2

• 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: (8'R,9'S,13'S,14'S,17'S)-carbonic acid 3-(17'-hydroxy-3'-methoxy-13'-methyl-7',8',9',11',12',13',14',15',16',17'-decahydro-6H-cyclopenta[a]phenanthren-17'-yl)-prop-2-ynyl ester methyl ester
• CAS: 530158-36-2
• 化学式: C₂₄H₃₀O₅
• 分子量: 398.499
• InChiKey: IZZPQRGZASKMLO-LBQHQWNISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.07
• 重原子数：
  29.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  64.99
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  4-甲氧基苯酚 、 (8'R,9'S,13'S,14'S,17'S)-carbonic acid 3-(17'-hydroxy-3'-methoxy-13'-methyl-7',8',9',11',12',13',14',15',16',17'-decahydro-6H-cyclopenta[a]phenanthren-17'-yl)-prop-2-ynyl ester methyl ester 在 tris(dibenzylideneacetone)dipalladium(0) chloroform complex 、 1,2-双(二苯基膦)乙烷 作用下， 以 1,4-二氧六环 为溶剂， 以82%的产率得到(8R,9S,13S,14S,17S)-17-spiro-{(2'R)-1',2'-epoxy-2'-[1''-(4''-methoxyphenoxy)vinyl]ethane}-3-methoxy-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthrene
  参考文献：
  名称：

  A Novel Methodology for the Synthesis of Cyclic Carbonates Based on the Palladium-Catalyzed Cascade Reaction of 4-Methoxycarbonyloxy-2-butyn-1-ols with Phenols, Involving a Novel Carbon Dioxide Elimination-Fixation Process

  摘要：

  A palladium-catalyzed CO2-recycling reaction has been developed. Reaction of 4-methoxycarbonyloxy-2-butyn-1-ols with phenols, carried out in the presence of a palladium catalyst, produces phenoxy-substituted cyclic carbonates by way of a pathway involving a CO2 elimination-fixation. A variety of propargylic alcohols and phenols participate in these reactions which yield cyclic carbonates with high efficiencies. Stereoselective construction of trans-cyclic carbonates is achieved by using nonsymmetric substrates. Highly enantioselective reactions occur when (S)-BINAP is used as a ligand. Reaction of 4-phenoxycarbonyloxy2-butyn-1-ol in the presence of the palladium catalyst yields the corresponding cyclic carbonates via a three-component decomposition-reconstruction process.

  DOI：

  10.1021/ja0340681
• 作为产物：
  描述：

  氯甲酸甲酯 、 3-Methoxy-17α-(3-hydroxy-propin-(1)-yl)-oestratrien-(1,3,5)-ol-(17β) 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以100%的产率得到(8'R,9'S,13'S,14'S,17'S)-carbonic acid 3-(17'-hydroxy-3'-methoxy-13'-methyl-7',8',9',11',12',13',14',15',16',17'-decahydro-6H-cyclopenta[a]phenanthren-17'-yl)-prop-2-ynyl ester methyl ester
  参考文献：
  名称：

  A Novel Methodology for the Synthesis of Cyclic Carbonates Based on the Palladium-Catalyzed Cascade Reaction of 4-Methoxycarbonyloxy-2-butyn-1-ols with Phenols, Involving a Novel Carbon Dioxide Elimination-Fixation Process

  摘要：

  A palladium-catalyzed CO2-recycling reaction has been developed. Reaction of 4-methoxycarbonyloxy-2-butyn-1-ols with phenols, carried out in the presence of a palladium catalyst, produces phenoxy-substituted cyclic carbonates by way of a pathway involving a CO2 elimination-fixation. A variety of propargylic alcohols and phenols participate in these reactions which yield cyclic carbonates with high efficiencies. Stereoselective construction of trans-cyclic carbonates is achieved by using nonsymmetric substrates. Highly enantioselective reactions occur when (S)-BINAP is used as a ligand. Reaction of 4-phenoxycarbonyloxy2-butyn-1-ol in the presence of the palladium catalyst yields the corresponding cyclic carbonates via a three-component decomposition-reconstruction process.

  DOI：

  10.1021/ja0340681