tert-butyl-6-acetylnaphthalen-2-ylcarbamate | 1313516-29-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: tert-butyl-6-acetylnaphthalen-2-ylcarbamate
• 英文别名: N-tert-butoxycarbonyl-6-acetyl-2-naphthylamine；tert-butyl N-(6-acetylnaphthalen-2-yl)carbamate
• CAS: 1313516-29-8
• 化学式: C₁₇H₁₉NO₃
• 分子量: 285.343
• InChiKey: ZXSAQJCGGGYICB-UHFFFAOYSA-N

物化性质

• 沸点：
  399.2±15.0 °C(Predicted)
• 密度：
  1.168±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  tert-butyl-6-acetylnaphthalen-2-ylcarbamate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以99%的产率得到1-(6-氨基萘-2-基)乙酮
  参考文献：
  名称：

  Site-specific fluorescence spectrum detection and characterization of hASIC1a channels upon toxin mambalgin-1 binding in live mammalian cells

  摘要：

  在活体哺乳动物细胞中应用荧光光谱检测，对毒素结合后hASIC1a通道的构象响应进行了分析。

  DOI：

  10.1039/c5cc01418b
• 作为产物：
  描述：

  三氟甲烷磺酸-6-溴-2-萘酯 在 copper(l) iodide 、 1,3-双(二苯基膦)丙烷 、 palladium diacetate 、 potassium carbonate 、 三乙胺 、 N,N'-二甲基乙二胺 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 26.0h， 生成 tert-butyl-6-acetylnaphthalen-2-ylcarbamate
  参考文献：
  名称：

  Enantiospecific Synthesis of Genetically Encodable Fluorescent Unnatural Amino Acid l-3-(6-Acetylnaphthalen-2-ylamino)-2-aminopropanoic Acid

  摘要：

  Fluorescent unnatural amino acids (UAAs), when genetically incorporated into proteins, can provide unique advantages for imaging biological processes in vivo. Synthesis of optically pure L-enantiomer of fluorescent UAAs is crucial for their effective application in live cells. An efficient six-step synthesis of L-3-(6-acetylnaphthalen-2-ylamino)-2-aminopropanoic acid (L-Anap), a genetically encodable and polarity-sensitive fluorescent UAA, has been developed. The synthesis takes advantage of a high-yield and enantiospecific Fukuyama-Mitsunobu reaction as the key transformation.

  DOI：

  10.1021/jo2007626

文献信息

• Hypoxia-Activated Prodrugs: Substituent Effects on the Properties of Nitro <i>seco</i>-1,2,9,9a-Tetrahydrocyclopropa[<i>c</i>]benz[<i>e</i>]indol-4-one (nitroCBI) Prodrugs of DNA Minor Groove Alkylating Agents
  作者：Moana Tercel、Graham J. Atwell、Shangjin Yang、Ralph J. Stevenson、K. Jane Botting、Maruta Boyd、Eileen Smith、Robert F. Anderson、William A. Denny、William R. Wilson、Frederik B. Pruijn

  DOI：10.1021/jm901202b

  日期：2009.11.26

  Nitrochloromethylbenzindolines (nitroCBIs) are a new class of hypoxia-activated prodrugs for antitumor therapy. The recently reported prototypes undergo hypoxia-selective metabolism to form potent DNA minor groove alkylating agents and are selectively toxic to some but not all hypoxic tumor cell lines. Here we report a series of 31 analogues that bear an extra electron-withdrawing substituent that serves to raise the one-electron reduction potential of the nitroCBI. We identify a subset of compounds, those with a basic side chain and sulfonamide or carboxamide substituent, that have consistently high hypoxic selectivity. The best of these, with a 7-sulfonamide substituent, displays hypoxic cytotoxicity ratios of 275 and 330 in Skov3 and HT29 human tumor cell lines, respectively. This compound (28) is efficiently and selectively metabolized to the corresponding aminoCBI, is selectively cytotoxic tinder hypoxia in all 11 cell lines examined, and demonstrates activity against hypoxic tumor cells in a human tumor xenograft in vivo.
• Enantiospecific Synthesis of Genetically Encodable Fluorescent Unnatural Amino Acid <scp>l</scp>-3-(6-Acetylnaphthalen-2-ylamino)-2-aminopropanoic Acid
  作者：Zheng Xiang、Lei Wang

  DOI：10.1021/jo2007626

  日期：2011.8.5

  Fluorescent unnatural amino acids (UAAs), when genetically incorporated into proteins, can provide unique advantages for imaging biological processes in vivo. Synthesis of optically pure L-enantiomer of fluorescent UAAs is crucial for their effective application in live cells. An efficient six-step synthesis of L-3-(6-acetylnaphthalen-2-ylamino)-2-aminopropanoic acid (L-Anap), a genetically encodable and polarity-sensitive fluorescent UAA, has been developed. The synthesis takes advantage of a high-yield and enantiospecific Fukuyama-Mitsunobu reaction as the key transformation.
• Site-specific fluorescence spectrum detection and characterization of hASIC1a channels upon toxin mambalgin-1 binding in live mammalian cells
  作者：Ming Wen、Xiaoqi Guo、Peibei Sun、Liang Xiao、Juan Li、Ying Xiong、Jin Bao、Tian Xue、Longhua Zhang、Changlin Tian

  DOI：10.1039/c5cc01418b

  日期：——

  Fluorescence spectrum detection in live mammalian cells was applied for conformational response analysis of hASIC1a channels upon toxin binding.

  在活体哺乳动物细胞中应用荧光光谱检测，对毒素结合后hASIC1a通道的构象响应进行了分析。