2(S)-3,3-dimethyl-1-(2-{5-[4-(phenylmethoxy)phenyl]pent-4-enoyl}pyrrolidinyl)pentane-1,2-dione | 457606-38-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2(S)-3,3-dimethyl-1-(2-{5-[4-(phenylmethoxy)phenyl]pent-4-enoyl}pyrrolidinyl)pentane-1,2-dione
• 英文别名: (S,E)-1-(2-(5-(4-(benzyloxy)phenyl)pent-4-enoyl)pyrrolidin-1-yl)-3,3-dimethylpentane-1,2-dione；3,3-dimethyl-1-[(2S)-2-[(E)-5-(4-phenylmethoxyphenyl)pent-4-enoyl]pyrrolidin-1-yl]pentane-1,2-dione
• CAS: 457606-38-1
• 化学式: C₂₉H₃₅NO₄
• 分子量: 461.601
• InChiKey: YIWAKPCCOGNBLI-HGJFNOKFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  34
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  63.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2(S)-3,3-dimethyl-1-(2-{5-[4-(phenylmethoxy)phenyl]pent-4-enoyl}pyrrolidinyl)pentane-1,2-dione 在 palladium on activated charcoal 氢气 作用下， 以 乙酸乙酯 为溶剂， 以61%的产率得到2(S)-3,3-dimethyl-1-{2-[5-(4-hydroxyphenyl)pentanoyl]pyrrolidinyl}pentane-1,2-dione
  参考文献：
  名称：

  Synthesis of Ketone Analogues of Prolyl and Pipecolyl Ester FKBP12 Ligands

  摘要：

  The recently discovered small-molecule ligands for the peptidyl and prolyl isomerases (PPIase) of FKBP12 have been shown to possess powerful neuroprotective and neuroregenerative effects. Ketone analogues of the prolyl and pipecolyl esters, which mimic only the FKBP binding domain portion of FK506, are proposed and an efficient synthetic strategy is presented in this report, along with the preliminary results of in vitro and in vivo biological studies.

  DOI：

  10.1021/jm0200456
• 作为产物：
  描述：

  methyl 2(S)-2-oxo-2-(2-pent-4-enoylpyrrolidinyl)acetate 在 palladium diacetate 、 三乙胺 、 三(邻甲基苯基)磷 作用下， 以 四氢呋喃 为溶剂， 反应 2.5h， 生成 2(S)-3,3-dimethyl-1-(2-{5-[4-(phenylmethoxy)phenyl]pent-4-enoyl}pyrrolidinyl)pentane-1,2-dione
  参考文献：
  名称：

  Synthesis of Ketone Analogues of Prolyl and Pipecolyl Ester FKBP12 Ligands

  摘要：

  The recently discovered small-molecule ligands for the peptidyl and prolyl isomerases (PPIase) of FKBP12 have been shown to possess powerful neuroprotective and neuroregenerative effects. Ketone analogues of the prolyl and pipecolyl esters, which mimic only the FKBP binding domain portion of FK506, are proposed and an efficient synthetic strategy is presented in this report, along with the preliminary results of in vitro and in vivo biological studies.

  DOI：

  10.1021/jm0200456

文献信息

• A General and Highly Selective Chelate-Controlled Intermolecular Oxidative Heck Reaction
  作者：Jared H. Delcamp、Alexandria P. Brucks、M. Christina White

  DOI：10.1021/ja804120r

  日期：2008.8.27

  chelate-controlled intermolecular oxidative Heck reaction is reported that proceeds with a wide range of nonresonance stabilized alpha-olefin substrates and organoboron reagents to afford internal olefin products in good yields and outstanding regio- and E: Z stereoselectivities. Pd-H isomerization, common in many Heck reactions, is not observed under these mild, oxidative conditions. This is evidenced

  据报道，一种新型螯合物控制的分子间氧化 Heck 反应与各种非共振稳定的 α-烯烃底物和有机硼试剂一起进行，以良好的收率和出色的区域和 E:Z 立体选择性提供内烯烃产品。在许多 Heck 反应中常见的 Pd-H 异构化在这些温和的氧化条件下未观察到。这可以通过出色的 E:Z 选择性（在所有检查的情况下 >20:1）、近端立体中心的光学纯度没有侵蚀以及对未受保护的醇的耐受性来证明。值得注意的是，单一金属/配体组合，Pd/双-亚砜配合物 1，在广泛的偶联伙伴上催化该反应。鉴于高选择性和广泛的范围，
• Synthesis of Ketone Analogues of Prolyl and Pipecolyl Ester FKBP12 Ligands
  作者：Yong-Qian Wu、Douglas E. Wilkinson、David Limburg、Jia-He Li、Hansjorg Sauer、Doug Ross、Shi Liang、Dawn Spicer、Heather Valentine、Mike Fuller、Hong Guo、Pam Howorth、Raj Soni、Yi Chen、Joseph P. Steiner、Gregory S. Hamilton

  DOI：10.1021/jm0200456

  日期：2002.8.1

  The recently discovered small-molecule ligands for the peptidyl and prolyl isomerases (PPIase) of FKBP12 have been shown to possess powerful neuroprotective and neuroregenerative effects. Ketone analogues of the prolyl and pipecolyl esters, which mimic only the FKBP binding domain portion of FK506, are proposed and an efficient synthetic strategy is presented in this report, along with the preliminary results of in vitro and in vivo biological studies.