[2-(3-Hydroxy-5-methoxy-1,4-dioxo-1,4-dihydro-naphthalen-2-yl)-3-methoxy-5-methyl-phenyl]-carbamic acid tert-butyl ester | 152937-75-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: [2-(3-Hydroxy-5-methoxy-1,4-dioxo-1,4-dihydro-naphthalen-2-yl)-3-methoxy-5-methyl-phenyl]-carbamic acid tert-butyl ester
• CAS: 152937-75-2
• 化学式: C₂₄H₂₅NO₇
• 分子量: 439.465
• InChiKey: IPAKEHSPNVXOFU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.71
• 重原子数：
  32.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  111.16
• 氢给体数：
  2.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  [2-(3-Hydroxy-5-methoxy-1,4-dioxo-1,4-dihydro-naphthalen-2-yl)-3-methoxy-5-methyl-phenyl]-carbamic acid tert-butyl ester 在 硫酸 、 三溴化硼 、 sodium hydride 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 4.0h， 生成 1,7-dihydroxy-3-methyl-6,11-dioxo-6,11-dihydro-5H-benzo[b]carbazole-5-carbonitrile
  参考文献：
  名称：

  拟定结构的苯并[ b ]咔唑并醌用于前动霉素

  摘要：

  通过钯和铜催化的2-溴萘甲醌与芳基锡烷的偶联，然后闭环，N-氰化和去甲基化，可以合成具有拟用于前激霉素的结构的N-氰基苯并[ b ]咔唑醌。出乎意料的是，闭环反应通过空前的重排反应也产生了区域异构体。

  DOI：

  10.1016/s0040-4039(00)60664-0
• 作为产物：
  描述：

  2-bromo-5-hydroxy-[1,4]naphthoquinone 在 叔丁基过氧化氢 、 四(三苯基膦)钯 、 苄基三甲基氢氧化铵 、 copper(I) bromide 、 silver(l) oxide 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 氯仿 、 水 为溶剂， 反应 3.0h， 生成 [2-(3-Hydroxy-5-methoxy-1,4-dioxo-1,4-dihydro-naphthalen-2-yl)-3-methoxy-5-methyl-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

文献信息

• Synthesis of the benzo[b]carbazoloquinone with the structure proposed for prekinamycin
  作者：Antonio M. Echavarren、Nuria Tamayo、M. Carmen Paredes

  DOI：10.1016/s0040-4039(00)60664-0

  日期：1993.9

  synthesis of the N-cyano benzo[b]carbazolequinone with the structure proposed for prekinamycin has been achieved by palladium and copper catalyzed coupling of a 2-bromonaphthoquinone with an arylstannane followed by ring closure, N-cyanation, and demethylation. Unexpectedly, the ring closure reaction gave also a regioisomer by an unprecedented rearrangement reaction.

  通过钯和铜催化的2-溴萘甲醌与芳基锡烷的偶联，然后闭环，N-氰化和去甲基化，可以合成具有拟用于前激霉素的结构的N-氰基苯并[ b ]咔唑醌。出乎意料的是，闭环反应通过空前的重排反应也产生了区域异构体。
• 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.