(E)-1-[(1S,2R,3R,5S)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-vinyl-cyclopentyl]-oct-1-en-3-one | 470700-71-1

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: (E)-1-[(1S,2R,3R,5S)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-vinyl-cyclopentyl]-oct-1-en-3-one
• 英文别名: (E)-1-[(1S,2R,3R,5S)-3,5-bis[[tert-butyl(dimethyl)silyl]oxy]-2-ethenylcyclopentyl]oct-1-en-3-one
• CAS: 470700-71-1
• 化学式: C₂₇H₅₂O₃Si₂
• 分子量: 480.879
• InChiKey: JXMCBBYIQZKXQB-ZLBSDSRMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.29
• 重原子数：
  32
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-1-[(1S,2R,3R,5S)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-vinyl-cyclopentyl]-oct-1-en-3-one 在 (S)-2-甲基-CBS-恶唑硼烷 、 (R)-2-甲基-CBS-恶唑硼烷 pyridinium chlorochromate 、 儿萘酚硼烷 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 32.0h， 生成 (E)-(S)-1-[(1R,2S,3S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-vinyl-cyclopentyl]-oct-1-en-3-ol
  参考文献：
  名称：

  Stereodivergent Synthesis of All 15-F₂ Isoprostanes

  摘要：

  Isoprostanes, lipid metabolites generated from free radical oxidation of membrane-bound arachidonic acid, have been detected in organisms subjected to oxidative stress; however, the function and cellular targets of the isoprostanes are unclear. As an initial step toward studying the biological role of these molecules, we report the preparation of all known and anticipated 15-F2 isoprostanes. The stereodivergent strategy to the complete isoprostane library features a ring-opening metathesis to introduce the cis-alkyl side chains that are characteristic of this class of molecules. Resolution to the individual stereoisomers can be accomplished by either a catalytic asymmetric reduction or an auxiliary-based separation protocol. In either case, the individual isomers can be converted to the corresponding 15-F2 isoprostanes through a straightforward functionalization of the carboxylic acid-containing side chain. The availability of this complete 15-F2 isoprostane library, containing both known and anticipated lipid metabolites, allows for the first time the side-by-side evaluation of these compounds in a variety of biological assays.

  DOI：

  10.1021/ja027154u
• 作为产物：
  描述：

  (4R)-(+)-T-丁基二甲基硅氧-1-酮 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 4-二甲氨基吡啶 、 二异丁基氢化铝 、 三乙胺 作用下， 以 二氯甲烷 、 丙酮 、 甲苯 、 苯 为溶剂， 反应 80.0h， 生成 (E)-1-[(1S,2R,3R,5S)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-vinyl-cyclopentyl]-oct-1-en-3-one
  参考文献：
  名称：

  Selective Synthesis of ent-15-epi-F_2t-Isoprostane and a Deuterated Derivative

  摘要：

  异构烷醇是一类新兴的脂质代谢产物，其生理特性尚不完全理解。本文描述了选择性合成在初步筛选实验中活跃的异构体 ent-15-epi-F2t-isoprostane 的过程。该合成采用了对称选择性交叉重排反应，基于手性富集的二乙烯环戊烯中间体，选择性区分了目标的侧链。这条合成路线从易得的起始材料出发，经过14个步骤，合成了异构烷醇及其一个 d4 标记的类似物。

  DOI：

  10.1055/s-2007-983768

文献信息

• Selective Synthesis of <b><i>ent</i></b>-15-<b><i>epi</i></b>-F_2t-Isoprostane and a Deuterated Derivative
  作者：Marc Snapper、Manami Shizuka

  DOI：10.1055/s-2007-983768

  日期：2007.7

  Isoprostanes are an emerging class of lipid metabolites whose physiological properties are not well understood. The selective synthesis of ent-15-epi-F2t-isoprostane, an isomer active in a preliminary screening assay is described. The synthesis features a regioselective cross-metathesis on an enantiomerically enriched divinyl cyclopentyl intermediate to selectively differentiate the side-chains of the target. The route provides the isoprostane, as well as a d 4-labeled analogue, in 14 steps from readily available starting material­s.

  异构烷醇是一类新兴的脂质代谢产物，其生理特性尚不完全理解。本文描述了选择性合成在初步筛选实验中活跃的异构体 ent-15-epi-F2t-isoprostane 的过程。该合成采用了对称选择性交叉重排反应，基于手性富集的二乙烯环戊烯中间体，选择性区分了目标的侧链。这条合成路线从易得的起始材料出发，经过14个步骤，合成了异构烷醇及其一个 d4 标记的类似物。
• Stereodivergent Synthesis of All 15-F₂ Isoprostanes
  作者：Thomas O. Schrader、Marc L. Snapper

  DOI：10.1021/ja027154u

  日期：2002.9.1

  Isoprostanes, lipid metabolites generated from free radical oxidation of membrane-bound arachidonic acid, have been detected in organisms subjected to oxidative stress; however, the function and cellular targets of the isoprostanes are unclear. As an initial step toward studying the biological role of these molecules, we report the preparation of all known and anticipated 15-F2 isoprostanes. The stereodivergent strategy to the complete isoprostane library features a ring-opening metathesis to introduce the cis-alkyl side chains that are characteristic of this class of molecules. Resolution to the individual stereoisomers can be accomplished by either a catalytic asymmetric reduction or an auxiliary-based separation protocol. In either case, the individual isomers can be converted to the corresponding 15-F2 isoprostanes through a straightforward functionalization of the carboxylic acid-containing side chain. The availability of this complete 15-F2 isoprostane library, containing both known and anticipated lipid metabolites, allows for the first time the side-by-side evaluation of these compounds in a variety of biological assays.