N,N-Diethyl-4-<(tert-butyldimethylsilyl)oxy>-1,3-benzodioxole-5-carboxamide | 120882-38-4

• 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-butyldimethylsilyl)oxy>-1,3-benzodioxole-5-carboxamide
• 英文别名: 4-(tert-butyl-dimethyl-silanyloxy)-N,N-diethyl-1,3-benzodioxole-5-carboxamide；N,N-diethyl-4-(tert-butyldimethylsilyloxy)-1,3-benzodioxole-5-carboxamide；N,N-diethyl-4-(tert-butylmethylsiloxy)-1,3-benzodioxole-5-carboxamide；N,N-Diethyl-4-[(tert-butyldimethylsilyl)oxy]-1,3-benzodioxole-5-carboxamide；4-[tert-butyl(dimethyl)silyl]oxy-N,N-diethyl-1,3-benzodioxole-5-carboxamide
• CAS: 120882-38-4
• 化学式: C₁₈H₂₉NO₄Si
• 分子量: 351.518
• InChiKey: GYTDAZAJBZBKQG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.28
• 重原子数：
  24
• 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-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
• 作为产物：
  描述：

  1,2-二羟基苯基二乙基氨基甲酸酯 在 咪唑 、 四甲基乙二胺 、 仲丁基锂 、 potassium carbonate 、 copper(II) oxide 作用下， 以 四氢呋喃 、 二氯甲烷 、 环己烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 N,N-Diethyl-4-<(tert-butyldimethylsilyl)oxy>-1,3-benzodioxole-5-carboxamide
  参考文献：
  名称：

  (.+-.)-pancrastatin 的全合成

  摘要：

  La 合成 de l'octahydro pentahydroxy-1,2,3,4,7 dioxolo-1,3 [4,5-j] phenanthridinone-6 a ete effectuee; le controlestereochimique de la synthese est 实现 par une serie de reactor de fonctionalisations cis vicinales

  DOI：

  10.1021/ja00195a039

文献信息

• Synthesis of pancratistatin models
  作者：Rosangela S.C. Lopes、Claudio C. Lopes、Clayton H. Heathcock

  DOI：10.1016/s0040-4039(00)61773-2

  日期：1992.11

  Two model syntheses for the phenanthridone core of the cytotoxic alkaloid pancratistatin are reported. The key maneuver in these syntheses is 1,4-addition of an ortho-lithiated benzamide derivative to 1-nitrocyclohexene. The resulting 2-aryl-1-nitrocyclohexanes (6 and 11) are further transformed into the pancratistatin models 2 and 3.

  报道了细胞毒性生物碱潘克拉斯汀的菲啶酮核心的两种模型合成。这些合成中的关键操作是将邻甲硅烷基化的苯甲酰胺衍生物1，4-加成到1-硝基环己烯上。所得的2-芳基-1-硝基环己烷（6和11）被进一步转化为pancratistatin模型2和3。
• Convergent Synthesis of Pancratistatin from Piperonal and Xylose
  作者：Johan Hygum Dam、Robert Madsen

  DOI：10.1002/ejoc.200900719

  日期：2009.9

  A synthesis of the antitumour agent pancratistatin is described from piperonal and D-xylose. Piperonal is converted into cinnamyl bromide 11 while methyl 5-iodoribofuranoside 12 is derived from xylose. The allylic bromide and the iodocarbohydrate are combined in a zinc-mediated tandem reaction to afford a highly functionalised 1,7-diene, which is then converted into the corresponding cyclohexene by

  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)
• 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.
• 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.
• Total synthesis of (.+-.)-pancratistatin
  作者：Samuel Danishefsky、Joung Yon Lee

  DOI：10.1021/ja00195a039

  日期：1989.6

  La synthese de l'octahydro pentahydroxy-1,2,3,4,7 dioxolo-1,3 [4,5-j] phenanthridinone-6 a ete effectuee; le controle stereochimique de la synthese est realise par une serie de reactions de fonctionalisations cis vicinales

  La 合成 de l'octahydro pentahydroxy-1,2,3,4,7 dioxolo-1,3 [4,5-j] phenanthridinone-6 a ete effectuee; le controlestereochimique de la synthese est 实现 par une serie de reactor de fonctionalisations cis vicinales