4-hydroxy-6-iodo-1,3-benzodioxole-5-carboxylic acid | 905914-41-2

• 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: 4-hydroxy-6-iodo-1,3-benzodioxole-5-carboxylic acid
• CAS: 905914-41-2
• 化学式: C₈H₅IO₅
• 分子量: 308.029
• InChiKey: ODOKWPBKIYEUDI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  76
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-hydroxy-6-iodo-1,3-benzodioxole-5-carboxylic acid 在 偶氮二异丁腈 、 二苯基二硒醚 、 碘 、 三正丁基氢锡 、 碳酸氢钠 作用下， 以 四氢呋喃 、 苯 为溶剂， 反应 15.0h， 生成 <(+/-)-(4α,4aα,11bα)>-3,4,4a,11b-Tetrahydro-4-iodo-7-hydroxy-6H-<1,3>benzodioxolo<5,6-c><1>benzopyran-6-one
  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
• 作为产物：
  描述：

  N,N-Diethyl-4-<(tert-butyldimethylsilyl)oxy>-1,3-benzodioxole-5-carboxamide 在 disodium hydrogenphosphate 、 正丁基锂 、 四甲基乙二胺 、 trimethoxonium tetrafluoroborate 作用下， 以 四氢呋喃 、 正己烷 、 乙腈 为溶剂， 反应 21.0h， 生成 4-hydroxy-6-iodo-1,3-benzodioxole-5-carboxylic acid
  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.