2-[2-(tert-butoxycarbonyl)aminophenyl]-5-methoxy-1,4-naphthoquinone | 200508-14-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-[2-(tert-butoxycarbonyl)aminophenyl]-5-methoxy-1,4-naphthoquinone
• CAS: 200508-14-1
• 化学式: C₂₂H₂₁NO₅
• 分子量: 379.412
• InChiKey: JSVNJYZWMMROFF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  28.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  81.7
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  2-[2-(tert-butoxycarbonyl)aminophenyl]-5-methoxy-1,4-naphthoquinone 在 叔丁基过氧化氢 、 苄基三甲基氢氧化铵 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 2.0h， 生成 [2-(3-Hydroxy-5-methoxy-1,4-dioxo-1,4-dihydro-naphthalen-2-yl)-phenyl]-carbamic acid tert-butyl ester 、 [2-(3-Methoxy-2,7-dioxo-2,7-dihydro-1aH-1-oxa-cyclopropa[b]naphthalen-7a-yl)-phenyl]-carbamic acid tert-butyl ester
  参考文献：
  名称：

  Synthesis of benzo[b]carbazoloquinones by coupling of organostannanes with bromoquinones

  摘要：

  The synthesis of 5-carbonitrile-1,7-dihydroxy-3-methyl-5H-benzo[b]carbazole-6,11-dione, the quinone originally proposed as prekinamycin, was completed by using a palladium and copper catalyzed Stille reaction as the key step. A subsequent heterocyclization afforded a mixture of para(benzo[b]carbazole-6,11-dione) and ortho (benzo[a]carbazole-6,11-dione) quinones. A procedure for the N-cyanation of model indoles is also described. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)10085-0
• 作为产物：
  描述：

  2-bromo-5-hydroxy-[1,4]naphthoquinone 在 四(三苯基膦)钯 、 copper(I) bromide 、 silver(l) oxide 作用下， 以 1,4-二氧六环 、 氯仿 为溶剂， 反应 6.0h， 生成 2-[2-(tert-butoxycarbonyl)aminophenyl]-5-methoxy-1,4-naphthoquinone
  参考文献：
  名称：

  Synthesis of benzo[b]carbazoloquinones by coupling of organostannanes with bromoquinones

  摘要：

  The synthesis of 5-carbonitrile-1,7-dihydroxy-3-methyl-5H-benzo[b]carbazole-6,11-dione, the quinone originally proposed as prekinamycin, was completed by using a palladium and copper catalyzed Stille reaction as the key step. A subsequent heterocyclization afforded a mixture of para(benzo[b]carbazole-6,11-dione) and ortho (benzo[a]carbazole-6,11-dione) quinones. A procedure for the N-cyanation of model indoles is also described. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)10085-0

文献信息

• Synthesis of benzo[b]carbazoloquinones by coupling of organostannanes with bromoquinones
  作者：Antonio M Echavarren、Nuria Tamayo、Óscar de Frutos、Alicia García

  DOI：10.1016/s0040-4020(97)10085-0

  日期：1997.12

  The synthesis of 5-carbonitrile-1,7-dihydroxy-3-methyl-5H-benzo[b]carbazole-6,11-dione, the quinone originally proposed as prekinamycin, was completed by using a palladium and copper catalyzed Stille reaction as the key step. A subsequent heterocyclization afforded a mixture of para(benzo[b]carbazole-6,11-dione) and ortho (benzo[a]carbazole-6,11-dione) quinones. A procedure for the N-cyanation of model indoles is also described. (C) 1997 Elsevier Science Ltd.