5-((3aS,4S,6aR)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)-N-(undec-10-en-1-yl)pentanamide

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 生物素及其衍生物
• 英文名称: 5-((3aS,4S,6aR)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)-N-(undec-10-en-1-yl)pentanamide
• 英文别名: 5-[(3aS,4S,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]-N-undec-10-enylpentanamide
• 化学式: C₂₁H₃₇N₃O₂S
• 分子量: 395.61
• InChiKey: GNMRRTBWRKGKOW-BJLQDIEVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  27
• 可旋转键数：
  15
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  95.5
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-((3aS,4S,6aR)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)-N-(undec-10-en-1-yl)pentanamide 、 N-乙酰基神经鞘氨醇 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 以22%的产率得到
  参考文献：
  名称：

  One-step labelling of sphingolipids via a scrambling cross-metathesis reaction

  摘要：

  在交叉甲基化反应条件下，鞘磷脂衍生物骨架中的烷基链可与功能化（标记）侧链进行一步交换。

  DOI：

  10.1039/b508132g

文献信息

• Synthesis and evaluation of locostatin-based chemical probes towards PEBP-proteins
  作者：Jorin Hoogenboom、Martijn Fiers、Richard Immink、Han Zuilhof、Tom Wennekes

  DOI：10.1016/j.tetlet.2016.04.071

  日期：2016.6

  Phosphatidyl ethanolamine-binding proteins (PEBPs) are implicated in various critical physiological processes in all eukaryotes. Among them is Flowering Locus T (FT), the protein recently discovered as the vital flowering hormone in plants. Small molecule inhibitors and activators of FT could provide control over plant flowering and are therefore an interesting target for industrial agriculture. No small molecule inhibitors or activators are known for FT, but for a structurally similar PEBP, RKIP, an inhibitor called locostatin has been reported to covalently bind in the RKIP ligand binding pocket. Herein, we report the synthesis of novel locostatin-based chemical PEBP probes and evaluate their ability and selectivity towards the binding of FT and RKIP. (C) 2016 Elsevier Ltd. All rights reserved.
• Sphingolipids
  申请人：Ettmayer Peter

  公开号：US20080262254A1

  公开（公告）日：2008-10-23

  The use of a metathesis catalyst in the preparation of a functionalized sphingolipid.
• One-step labelling of sphingolipids via a scrambling cross-metathesis reaction
  作者：Peter Nussbaumer、Peter Ettmayer、Carsten Peters、Daniela Rosenbeiger、Klemens Högenauer

  DOI：10.1039/b508132g

  日期：——

  The alkyl chain in the backbone of sphingosine derivatives can be exchanged with functionalised (labelled) side chains in a single step under cross-metathesis reaction conditions.

  在交叉甲基化反应条件下，鞘磷脂衍生物骨架中的烷基链可与功能化（标记）侧链进行一步交换。