tert-butyl ((5S,8S,9E)-5-methyl-2,7-dioxo-1,6-diazacyclododec-3-en-8-yl)carbamate | 145958-01-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 大环内酰胺类
• 英文名称: tert-butyl ((5S,8S,9E)-5-methyl-2,7-dioxo-1,6-diazacyclododec-3-en-8-yl)carbamate
• 英文别名: tert-butyl ((5S,8S,E)-5-methyl-2,7-dioxo-1,6-diazacyclododec-3-en-8-yl)carbamate
• CAS: 145958-01-6
• 化学式: C₁₆H₂₇N₃O₄
• 分子量: 325.408
• InChiKey: WCKSYZSGEUCWDP-OMJLJAAMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.24
• 重原子数：
  23.0
• 可旋转键数：
  1.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  96.53
• 氢给体数：
  3.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  tert-butyl ((5S,8S,9E)-5-methyl-2,7-dioxo-1,6-diazacyclododec-3-en-8-yl)carbamate 在 氢溴酸 、 溶剂黄146 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.75h， 生成 (9H-fluoren-9-yl)methyl (S)-3-methyl-1-((5S,8S,E)-5-methyl-2,7-dioxo-1,6-diazacyclododec-3-en-8-ylamino)-1-oxobutan-2-ylcarbamate
  参考文献：
  名称：

  Syntheses and cytotoxicity of syringolin B-based proteasome inhibitors

  摘要：

  The concise and modular total synthesis of the bacterial natural product and irreversible proteasome inhibitor syringolin B has been achieved. This synthesis has enabled the ready preparation of three diverse, structurally modified syringolin derivatives. The actions of these compounds in inhibiting the proliferation of neuroblastoma cell lines was evaluated, and significant enhancements in potency compared to the natural product were realized. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.09.048
• 作为产物：
  描述：

  Nε-diethylphosphonacetyl-Nα-Boc-Lys-OH 在 N-羟基丁二酰亚胺 、 四甲基乙二胺 、 zinc trifluoromethanesulfonate 、 戴斯-马丁氧化剂 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 35.5h， 生成 tert-butyl ((5S,8S,9E)-5-methyl-2,7-dioxo-1,6-diazacyclododec-3-en-8-yl)carbamate
  参考文献：
  名称：

  Syntheses and cytotoxicity of syringolin B-based proteasome inhibitors

  摘要：

  The concise and modular total synthesis of the bacterial natural product and irreversible proteasome inhibitor syringolin B has been achieved. This synthesis has enabled the ready preparation of three diverse, structurally modified syringolin derivatives. The actions of these compounds in inhibiting the proliferation of neuroblastoma cell lines was evaluated, and significant enhancements in potency compared to the natural product were realized. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.09.048

文献信息

• The synthesis of glidobactin A
  作者：Ulrich Schmidt、Andreas Kleefeldt、Rainer Mangold

  DOI：10.1039/c39920001687

  日期：——

  Glidobactin A, a member of the antibiotic families glidobactins and cepafungins, which was previously isolated from culture filtrates of the Gram-negative bacterium Polyangium brachysporum sp. nov., is synthesized.

  一种名为Glidobactin A的抗生素，属于glidobactins和cepafungins抗生素家族，先前从革兰氏阴性菌新种短孢多拟青霉的培养滤液中分离得到，现已合成。
• Total Synthesis of Luminmycin A, a Cryptic Natural Product from <i>Photorhabdus Luminescens</i>
  作者：Phil Servatius、Tanja Stach、Uli Kazmaier

  DOI：10.1002/ejoc.201900460

  日期：2019.6.2

  Luminmycin A, a natural proteasome inhibitor has been synthesized for the first time. Key steps are an intramolecular Horner–Wadsworth–Emmons reaction and a PPh3‐catalyzed isomerization of a acetylenic fatty acid ester, giving access to the double unsaturated fatty acid side chain.

  首次合成了天然蛋白酶体抑制剂LuminmycinA。关键步骤是分子内霍纳-沃兹沃思-埃蒙斯反应和炔属脂肪酸酯的PPh 3催化异构化，从而可以进入双不饱和脂肪酸侧链。