N-(4-methoxybenzyl)-4,5-dimethoxy-2-[(trimethylsilyl)ethynyl]benzamide | 848061-26-7

• 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: N-(4-methoxybenzyl)-4,5-dimethoxy-2-[(trimethylsilyl)ethynyl]benzamide
• 英文别名: 4,5-dimethoxy-N-[(4-methoxyphenyl)methyl]-2-(2-trimethylsilylethynyl)benzamide
• CAS: 848061-26-7
• 化学式: C₂₂H₂₇NO₄Si
• 分子量: 397.546
• InChiKey: NKKIMACRSBCJMB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.87
• 重原子数：
  28
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  56.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(4-methoxybenzyl)-4,5-dimethoxy-2-[(trimethylsilyl)ethynyl]benzamide 在 potassium fluoride 、 水 、 碘 、 碳酸氢钠 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 1.5h， 生成 3-[1-Iodo-meth-(E)-ylidene]-5,6-dimethoxy-2-(4-methoxy-benzyl)-2,3-dihydro-isoindol-1-one
  参考文献：
  名称：

  Regio- and Stereoselective Synthesis of Isoindolin-1-ones via Electrophilic Cyclization

  摘要：

  A variety of substituted isoindolin-l-ones are readily prepared in good to excellent yields under very mild reaction conditions by the reaction of o-(1-alkynyl)benzamides with ICI, I-2, and NBS. In a few cases, substituted isoquinolin-1-ones were obtained as the major product instead. This methodology accommodates various alkynyl amides and functional groups and has been successfully extended to heterocyclic starting materials. This chemistry has been successfully applied to the synthesis of a biologically interesting alkaloid, cepharanone B.

  DOI：

  10.1021/jo048007c
• 作为产物：
  描述：

  4,5-dimethoxy-2-iodobenzoyl chloride 在 吡啶 、 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 生成 N-(4-methoxybenzyl)-4,5-dimethoxy-2-[(trimethylsilyl)ethynyl]benzamide
  参考文献：
  名称：

  通过 2-(1-炔基) 苯甲酰胺的亲电环化反应区域选择性和立体选择性合成环状亚胺酸酯。更正

  摘要：

  2-(1-炔基)苯甲酰胺的亲电环化提供了高产率的环状亚胺酸酯，而不是先前报道的异吲哚啉-1-酮，其中环化在羰基的氧而不是酰胺官能团的氮上进行。X 射线晶体学和光谱技术已用于表征产品。特此提供更正以纠正先前的结构错误分配。

  DOI：

  10.1021/jo301958q

文献信息

• Solution-Phase Parallel Synthesis of a Multisubstituted Cyclic Imidate Library
  作者：Saurabh Mehta、Jesse P. Waldo、Benjamin Neuenswander、Gerald H. Lushington、Richard C. Larock

  DOI：10.1021/co3001605

  日期：2013.5.13

  a diverse 71-member library of multisubstituted cyclic imidates is described. The key intermediates, 3-iodomethylene-containing cyclic imidates, are readily prepared in good to excellent yields by the palladium/copper-catalyzed cross-coupling of various o-iodobenzamides and terminal alkynes, followed by electrophilic cyclization with I2. These cyclic imidates were further functionalized by palladium-catalyzed

  描述了溶液相平行合成的多取代的环状酰亚胺的71元成员库。关键的中间体，即含3-碘亚甲基的环状酰亚胺，很容易通过钯/铜催化的各种邻碘苯甲酰胺和末端炔的交叉偶联，然后用I 2进行亲电环化，以良好至极好的收率制备。这些环状酰亚胺进一步被钯催化的铃木-宫浦，Sonogashira，羰基酰胺化和Heck化学法使用市售结构单元的子库进行功能化。
• Regio- and Stereoselective Synthesis of Cyclic Imidates via Electrophilic Cyclization of 2-(1-Alkynyl)benzamides. A Correction
  作者：Saurabh Mehta、Tuanli Yao、Richard C. Larock

  DOI：10.1021/jo301958q

  日期：2012.12.7

  The electrophilic cyclization of 2-(1-alkynyl)benzamides affords high yields of cyclic imidates, instead of the previously reported isoindolin-1-ones, where cyclization proceeds on the oxygen of the carbonyl group rather than the nitrogen of the amide functionality. X-ray crystallography and spectroscopic techniques have been used to characterize the products. A correction is hereby provided in order

  2-(1-炔基)苯甲酰胺的亲电环化提供了高产率的环状亚胺酸酯，而不是先前报道的异吲哚啉-1-酮，其中环化在羰基的氧而不是酰胺官能团的氮上进行。X 射线晶体学和光谱技术已用于表征产品。特此提供更正以纠正先前的结构错误分配。
• Regio- and Stereoselective Synthesis of Isoindolin-1-ones via Electrophilic Cyclization
  作者：Tuanli Yao、Richard C. Larock

  DOI：10.1021/jo048007c

  日期：2005.2.1

  A variety of substituted isoindolin-l-ones are readily prepared in good to excellent yields under very mild reaction conditions by the reaction of o-(1-alkynyl)benzamides with ICI, I-2, and NBS. In a few cases, substituted isoquinolin-1-ones were obtained as the major product instead. This methodology accommodates various alkynyl amides and functional groups and has been successfully extended to heterocyclic starting materials. This chemistry has been successfully applied to the synthesis of a biologically interesting alkaloid, cepharanone B.