(R)-1-benzoyl-5-(tert-butyldimethylsilyloxy)-1,4,5,6-tetrahydropyridazine | 909729-97-1

• 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: (R)-1-benzoyl-5-(tert-butyldimethylsilyloxy)-1,4,5,6-tetrahydropyridazine
• 英文别名: [(4R)-4-[tert-butyl(dimethyl)silyl]oxy-4,5-dihydro-3H-pyridazin-2-yl]-phenylmethanone
• CAS: 909729-97-1
• 化学式: C₁₇H₂₆N₂O₂Si
• 分子量: 318.491
• InChiKey: XBFCBOGDWZQLAU-OAHLLOKOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.91
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  41.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R)-1-benzoyl-5-(tert-butyldimethylsilyloxy)-1,4,5,6-tetrahydropyridazine 、 三甲基氰硅烷 在 sodium acetate 、 zinc trifluoromethanesulfonate 、 溶剂黄146 作用下， 反应 24.0h， 以57%的产率得到(3R,5R)-1-benzoyl-5-(tert-butyldimethylsilyloxy)-hexahydropyridazine-3-carbonitrile
  参考文献：
  名称：

  The efficient synthesis of (3R,5R)-5-hydroxypiperazic acid and its diastereomer using Lewis acid-promoted diastereoselective Strecker synthesis

  摘要：

  The stereoselective synthesis of (3R,5R)-5-hydroxypiperazic acid, a component of naturally occurring antibiotic cyclodepsipeptides, and its diastereomer was achieved via the use of Lewis acid-promoted diastereoselective Strecker synthesis as a key step, in which an interesting stereochemical reversal of diastereoselectivity by the choice of Lewis acid catalyst was observed. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.06.004
• 作为产物：
  描述：

  ethyl (3R)-4-chloro-3-[(1,1-dimethylethyl)dimethylsilyl]oxybutanoate 在 吡啶 、 二异丁基氢化铝 、 一水合肼 作用下， 以 乙醇 、 正己烷 为溶剂， 反应 19.0h， 生成 (R)-1-benzoyl-5-(tert-butyldimethylsilyloxy)-1,4,5,6-tetrahydropyridazine
  参考文献：
  名称：

  The efficient synthesis of (3R,5R)-5-hydroxypiperazic acid and its diastereomer using Lewis acid-promoted diastereoselective Strecker synthesis

  摘要：

  The stereoselective synthesis of (3R,5R)-5-hydroxypiperazic acid, a component of naturally occurring antibiotic cyclodepsipeptides, and its diastereomer was achieved via the use of Lewis acid-promoted diastereoselective Strecker synthesis as a key step, in which an interesting stereochemical reversal of diastereoselectivity by the choice of Lewis acid catalyst was observed. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.06.004

文献信息

• Progress toward the synthesis of piperazimycin A: exploration of the synthesis of γ-hydroxy and γ-chloropiperazic acids
  作者：J. Phillip Kennedy、John T. Brogan、Craig W. Lindsley

  DOI：10.1016/j.tetlet.2008.04.132

  日期：2008.6

  Employing Hamada's chemistry with MAOS optimization of several steps, an expedient route to key (3S,5S)- and (3R,5R)-gamma-hydroxy and (3R,5S)-gamma-chloropiperazic acids, was developed en route to a total synthesis of piperazimycin A. (C) 2008 Elsevier Ltd. All rights reserved.
• The efficient synthesis of (3R,5R)-5-hydroxypiperazic acid and its diastereomer using Lewis acid-promoted diastereoselective Strecker synthesis
  作者：Kazuishi Makino、Hang Jiang、Tatsuya Suzuki、Yasumasa Hamada

  DOI：10.1016/j.tetasy.2006.06.004

  日期：2006.7

  The stereoselective synthesis of (3R,5R)-5-hydroxypiperazic acid, a component of naturally occurring antibiotic cyclodepsipeptides, and its diastereomer was achieved via the use of Lewis acid-promoted diastereoselective Strecker synthesis as a key step, in which an interesting stereochemical reversal of diastereoselectivity by the choice of Lewis acid catalyst was observed. (c) 2006 Elsevier Ltd. All rights reserved.