N,N-diethyl-1-carbamyloxy-6-methoxynaphthalene | 530101-40-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N,N-diethyl-1-carbamyloxy-6-methoxynaphthalene
• 英文别名: (6-methoxynaphthalen-1-yl) N,N-diethylcarbamate
• CAS: 530101-40-7
• 化学式: C₁₆H₁₉NO₃
• 分子量: 273.332
• InChiKey: AMGBNSCHDDTCFT-UHFFFAOYSA-N

物化性质

• 熔点：
  83-85 °C
• 沸点：
  405.9±27.0 °C(Predicted)
• 密度：
  1.129±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N,N-diethyl-1-carbamyloxy-6-methoxynaphthalene 在 仲丁基锂 、 四亚甲基二胺 作用下， 以 四氢呋喃 为溶剂， 反应 16.0h， 生成
  参考文献：
  名称：

  Application of directed metallation in synthesis. Part 3: Studies in the synthesis of (±)-semivioxanthin and its analogues

  摘要：

  The synthesis of several analogues of (+/-)-semivioxanthin including five thiophene analogues, using directed metalation are reported. The strategy consisted of the synthesis of functionalized naphthalene or benzo[b]thiophene as building blocks followed by annelation of the pyrone. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)01599-5
• 作为产物：
  描述：

  6-甲氧基-1-萘满酮 在 lithium carbonate 、 sodium hydride 、 copper(I) bromide 、 lithium bromide 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 生成 N,N-diethyl-1-carbamyloxy-6-methoxynaphthalene
  参考文献：
  名称：

  Application of directed metallation in synthesis. Part 3: Studies in the synthesis of (±)-semivioxanthin and its analogues

  摘要：

  The synthesis of several analogues of (+/-)-semivioxanthin including five thiophene analogues, using directed metalation are reported. The strategy consisted of the synthesis of functionalized naphthalene or benzo[b]thiophene as building blocks followed by annelation of the pyrone. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)01599-5

文献信息

• Application of Directed Metalationin Synthesis. Part 5:Synthesis of CondensedSulfur-Oxygen Heterocycle via Novel Anionic Rearrangement-Cyclisation
  作者：Asish De、Chandrani Mukherjee、Sukanta Kamila

  DOI：10.1055/s-2003-40822

  日期：——

  Introduction of the methyl sulfanyl function in the ortho-position to O-carbamate functionality under standard directed metalation condition was followed by side-chain deprotonation with sec-butyl lithium at -78 °C. Upon warming to room temperature, the deprotonated species underwent intramolecular anionic rearrangement to afford N,N-diethyl-2-hydroxyarylthioacetamides. The rearranged products were cyclised with hot glacial acetic acid to afford condensed oxathiin-2-ones in excellent yields.

  在标准导向金属化条件下，将甲硫基功能引入到O-氨基甲酸酯的邻位后，在-78°C下用仲丁基锂进行侧链去质子化。升温至室温后，去质子化的物种经历分子内阴离子重排，得到N,N-二乙基-2-羟基芳基硫代乙酰胺。重排产物在热冰醋酸中环化，以优异的产率得到稠合的氧硫杂环己-2-酮。
• Application of directed metalation in synthesis. Part 6: A novel anionic rearrangement under directed metalation conditions leading to heteroannulation
  作者：Tarun Kanti Pradhan、Chandrani Mukherjee、Sukanta Kamila、Asish De

  DOI：10.1016/j.tet.2004.04.033

  日期：2004.6

  from easily available phenols is described. The key step in this synthesis is a hitherto unreported anionic rearrangement under directed metalation conditions. The rearrangement occurs after side chain deprotonation of a methyl sulfanyl group by an O-carbamate directed metalating group and the reaction mixture is kept at room temperature for 8–12 h. Acid-mediated cyclisation of the rearranged product

  描述了由容易获得的酚的短而有效的合成缩合的1，4-氧杂噻吩-2-酮。该合成过程中的关键步骤是在定向金属化条件下迄今未报道的阴离子重排。重排由甲基硫烷基的侧链的去质子化之后发生ø -氨基甲酸酯定向组金属化而得，并且将反应混合物在室温下保持8-12小时。重排产物的酸介导的环化作用提供[1,4]草苷-2-一。