N,N-diethyl-4-(tert-butylmethylsiloxy)-6-iodo-1,3-benzodioxole-5-carboxamide | 905914-40-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: N,N-diethyl-4-(tert-butylmethylsiloxy)-6-iodo-1,3-benzodioxole-5-carboxamide
• 英文别名: 4-(tert-butyl-dimethyl-silanyloxy)-N,N-diethyl-6-iodo-1,3-benzodioxole-5-carboxamide；N,N-diethyl-4-(tert-butyldimethylsilyloxy)-6-iodo-1,3-benzodioxole-5-carboxamide；4-[tert-butyl(dimethyl)silyl]oxy-N,N-diethyl-6-iodo-1,3-benzodioxole-5-carboxamide
• CAS: 905914-40-1
• 化学式: C₁₈H₂₈INO₄Si
• 分子量: 477.415
• InChiKey: WTJFZWIMZGXWJF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.89
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  48
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N,N-diethyl-4-(tert-butylmethylsiloxy)-6-iodo-1,3-benzodioxole-5-carboxamide 在 disodium hydrogenphosphate 、 偶氮二异丁腈 、 二苯基二硒醚 、 碘 、 三正丁基氢锡 、 trimethoxonium tetrafluoroborate 、 碳酸氢钠 作用下， 以 四氢呋喃 、 乙腈 、 苯 为溶剂， 反应 35.0h， 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 四甲基乙二胺 、 仲丁基锂 、 碘 作用下， 以 四氢呋喃 、 环己烷 为溶剂， 反应 2.25h， 以88%的产率得到N,N-diethyl-4-(tert-butylmethylsiloxy)-6-iodo-1,3-benzodioxole-5-carboxamide
  参考文献：
  名称：

  从胡椒醛和木糖中聚合合成潘克拉他汀

  摘要：

  描述了从胡椒醛和 D-木糖合成抗肿瘤剂 pancrastatin。胡椒醛转化为肉桂基溴化物 11，而甲基 5-碘代呋喃核糖苷 12 来自木糖。烯丙基溴和碘代碳水化合物在锌介导的串联反应中结合，得到高度官能化的 1,7-二烯，然后通过闭环烯烃复分解转化为相应的环己烯。随后的 Overman 重排、二羟基化和脱保护从两种起始材料中通过总共 25 个步骤提供了天然产物。最长的线性序列来自胡椒醛，分 18 个步骤产生 pancratastatin，总产率为 7.0%。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

  DOI：

  10.1002/ejoc.200900719

文献信息

• A chemoenzymatic total synthesis of ent-narciclasine
  作者：Maria Matveenko、Martin G. Banwell、Anthony C. Willis

  DOI：10.1016/j.tet.2008.01.113

  日期：2008.5

  The synthesis of the title compound [(-)-1] has been achieved, for the first time, by reacting the aryl boronic acid ester 4 with the amino-conduritol derivative 6 under Suzuki-Miyaura cross-coupling conditions then subjecting the product phenanthridinone 23 to a global deprotection process using trimethylsilyl bromide. The aromatic building block 4 was prepared in ten steps from piperonal while compound 6 was obtained in nine steps from the enantiomerically pure cis-1,2-dihydrocatechol 7. This last compound is available, in multi-gram quantities, through a whole-cell-mediated biotransformation of bromobenzene using genetically engineered organisms that over-express the responsible enzyme, namely toluene dioxygenase. Since the enantiomer of compound 7 is available by related means, the present work also represents a formal total synthesis of the alkaloid narciclasine [(+)-1]. The single-crystal X-ray analysis of compound 13 is reported. (C) 2008 Elsevier Ltd. All rights reserved.