methyl N-(2-cyclohexa-2,5-dien-1-ylphenyl)carbamate | 461398-60-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: methyl N-(2-cyclohexa-2,5-dien-1-ylphenyl)carbamate
• CAS: 461398-60-7
• 化学式: C₁₄H₁₅NO₂
• 分子量: 229.279
• InChiKey: IOFPTKDQCVQAPI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  苯基溴化硒 、 methyl N-(2-cyclohexa-2,5-dien-1-ylphenyl)carbamate 以 二氯甲烷 为溶剂， 反应 5.0h， 以69%的产率得到1S*,9aS*,4aR*-9-methoxycarbonyl-1-phenylseleno-1,2,4a,9a-tetrahydrocarbazole
  参考文献：
  名称：

  Rapid assembly of tetrahydrodibenzofurans and tetrahydrocarbazoles from benzene and o-iodophenols and o-iodoanilines: reductive radical arylation of benzene in action

  摘要：

  In the presence of catalytic benzeneselenol, generated in situ from diphenyl diselenide, tributyltin hydride brings about the radical addition of ortho-functionalized aryl iodides to benzene giving aryl cyclohexadienes. These may then be cyclized by means of standard electrophilic reagents. The use of o-methoxycarbamoyliodobenzene leads to a tetrahydrocarbazole, whereas o-iodobenzoic acid provides a tetrahydrodibenzopyranone. o-Iodophenois lead, overall, to tetrahydrodibenzofurans. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00288-0
• 作为产物：
  描述：

  N-(2-碘苯基)氨基甲酸甲酯 、 苯 在 偶氮二异丁腈 、 二苯基二硒醚 、 三正丁基氢锡 作用下， 以 苯 为溶剂， 生成 methyl N-(2-cyclohexa-2,5-dien-1-ylphenyl)carbamate 、 methyl N-(2-cyclohexa-2,4-dien-1-ylphenyl)carbamate
  参考文献：
  名称：

  Radical dearomatization of benzene leading to phenanthridine and phenanthridinone derivatives related to (±)-pancratistatin

  摘要：

  The synthesis of the phenanthridinone nucleus common to the Amaryllidaceae series of natural products is achieved by a sequence involving tributylstannane-mediated, benzeneselenol-catalyzed addition of ortho-nitrogen functionalized aryl radicals to benzene, yielding aryl-substituted cyclohexadienes. These cyclohexadienes may be manipulated by oxidative ring closure sequences to generate functionalized phenanthridines. Beginning from 2-hydroxy-6-iodopiperonic acid a key intermediate in the Danishefsky synthesis of (+/-)-pancratistatin is achieved in two steps. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.04.096

文献信息

• Radical dearomatization of benzene leading to phenanthridine and phenanthridinone derivatives related to (±)-pancratistatin
  作者：David Crich、Venkataramanan Krishnamurthy

  DOI：10.1016/j.tet.2006.04.096

  日期：2006.7

  The synthesis of the phenanthridinone nucleus common to the Amaryllidaceae series of natural products is achieved by a sequence involving tributylstannane-mediated, benzeneselenol-catalyzed addition of ortho-nitrogen functionalized aryl radicals to benzene, yielding aryl-substituted cyclohexadienes. These cyclohexadienes may be manipulated by oxidative ring closure sequences to generate functionalized phenanthridines. Beginning from 2-hydroxy-6-iodopiperonic acid a key intermediate in the Danishefsky synthesis of (+/-)-pancratistatin is achieved in two steps. (c) 2006 Elsevier Ltd. All rights reserved.
• Rapid assembly of tetrahydrodibenzofurans and tetrahydrocarbazoles from benzene and o-iodophenols and o-iodoanilines: reductive radical arylation of benzene in action
  作者：David Crich、Mousumi Sannigrahi

  DOI：10.1016/s0040-4020(02)00288-0

  日期：2002.4

  In the presence of catalytic benzeneselenol, generated in situ from diphenyl diselenide, tributyltin hydride brings about the radical addition of ortho-functionalized aryl iodides to benzene giving aryl cyclohexadienes. These may then be cyclized by means of standard electrophilic reagents. The use of o-methoxycarbamoyliodobenzene leads to a tetrahydrocarbazole, whereas o-iodobenzoic acid provides a tetrahydrodibenzopyranone. o-Iodophenois lead, overall, to tetrahydrodibenzofurans. (C) 2002 Elsevier Science Ltd. All rights reserved.