Prostaglandin F(1α)

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: Prostaglandin F(1α)
• 英文别名: 15-keto Prostaglandin F1alpha；7-[(1R,3R,5S)-3,5-dihydroxy-2-[(E,3S)-3-hydroxyoct-1-enyl]cyclopentyl]heptanoic acid
• 化学式: C₂₀H₃₆O₅
• 分子量: 356.503
• InChiKey: DZUXGQBLFALXCR-BMPPNWMBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  25
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  98
• 氢给体数：
  4
• 氢受体数：
  5

文献信息

• METHOD FOR INTRODUCING SUBSTITUENT INTO alpha,beta-UNSATURATED KETONE AND METHOD FOR SYNTHESIZING PROSTAGLANDIN USING THE SAME
  申请人：NATIONAL CENTER FOR GERIATRICS AND GERONTOLOGY

  公开号：US20210355061A1

  公开（公告）日：2021-11-18

  The present invention provides a method for introducing substituents into the α-position and the β-position of an α,β-unsaturated ketone, which not only can be used for the synthesis of a prostaglandin by a three-component coupling process, but also enables synthesis of a prostaglandin in a high yield by one-pot operation without requiring the use of a large excess amount of any of the three components required for the synthesis or using a highly toxic heavy metal as a catalyst or a solvent that is highly toxic to living bodies, and a method for synthesizing a prostaglandin using the same technical means. The method for introducing substituents into an α,β-unsaturated ketone according to the present invention is a method for introducing substituents into the carbon at the α-position and the carbon at the β-position of an α,β-unsaturated ketone, including: a first step of mixing alkyllithium and trialkylalkenyl tin in which tin atom binds to the vinyl position of the alkenyl group; a second step of mixing the mixture of the first step and dialkylzinc; a third step of mixing the mixture of the second step and an α,β-unsaturated ketone; and a fourth step of mixing the mixture of the third step and a trifluoromethanesulfonate compound.

  本发明提供了一种将取代基引入α，β-不饱和酮的α位和β位的方法，不仅可用于通过三组分偶联过程合成前列腺素，还能够通过一锅法高产率合成前列腺素，而无需使用大量超量的三种合成所需组分之一，也无需使用高毒性重金属作为催化剂或对生物体高毒的溶剂，并提供了一种利用相同技术手段合成前列腺素的方法。 根据本发明，将取代基引入α，β-不饱和酮的方法是一种将取代基引入α，β-不饱和酮的α位和β位碳的方法，包括：第一步，混合烷基锂和三烷基烯基锡，其中锡原子与烯基团的乙烯位结合；第二步，混合第一步的混合物和二烷基锌；第三步，混合第二步的混合物和α，β-不饱和酮；第四步，混合第三步的混合物和三氟甲磺酸盐化合物。