(-)-(R)-4-(5-phenyl-2H-tetrazol-2-yl)butan-2-ol | 1369529-09-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: (-)-(R)-4-(5-phenyl-2H-tetrazol-2-yl)butan-2-ol
• 英文别名: (2R)-4-(5-phenyltetrazol-2-yl)butan-2-ol
• CAS: 1369529-09-8
• 化学式: C₁₁H₁₄N₄O
• 分子量: 218.258
• InChiKey: JYYYQHMOASVGPP-SECBINFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  63.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (-)-(R)-4-(5-phenyl-2H-tetrazol-2-yl)butan-2-ol 、 (S)-(+)-alpha-甲氧基苯乙酸 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 生成 (R)-4-(5-phenyl-2H-tetrazol-2-yl)butan-2-yl (S)-2-methoxy-2-phenylacetate
  参考文献：
  名称：

  Lipase-catalyzed enantioseparation of alcohols containing a tetrazole ring

  摘要：

  A simple chemoenzymatic method for the preparation of optically active (5-aryltetrazolyl-2)-4-butan-2-ol, (5-aryltetrazolyl-2)-propan-2-ol, and their acetates has been developed. The starting compounds (5-aryltetrazolyl-2)-4-butan-2-one and (5-aryltetrazolyl-2)-propan-2-one were obtained by a Michael-type addition of 5-aryl substituted tetrazoles to methyl vinyl ketone, and alkylation of 5-aryl substituted tetrazoles with chloroacetone, respectively. Their reduction with sodium borohydride afforded racemic mixtures of (5-aryltetrazolyl-2)-4-butan-2-oles and (5-aryltetrazolyl-2)-propan-2-oles. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2012.01.015
• 作为产物：
  描述：

  (+/-)-4-(5-phenyl-2H-tetrazol-2-yl)butan-2-ol 在 Pseudomonas fluorescens Amano AK lipase 、 水 、 sodium hydroxide 作用下， 以 甲醇 、 甲基叔丁基醚 为溶剂， 反应 48.0h， 生成 (-)-(R)-4-(5-phenyl-2H-tetrazol-2-yl)butan-2-ol
  参考文献：
  名称：

  Lipase-catalyzed enantioseparation of alcohols containing a tetrazole ring

  摘要：

  A simple chemoenzymatic method for the preparation of optically active (5-aryltetrazolyl-2)-4-butan-2-ol, (5-aryltetrazolyl-2)-propan-2-ol, and their acetates has been developed. The starting compounds (5-aryltetrazolyl-2)-4-butan-2-one and (5-aryltetrazolyl-2)-propan-2-one were obtained by a Michael-type addition of 5-aryl substituted tetrazoles to methyl vinyl ketone, and alkylation of 5-aryl substituted tetrazoles with chloroacetone, respectively. Their reduction with sodium borohydride afforded racemic mixtures of (5-aryltetrazolyl-2)-4-butan-2-oles and (5-aryltetrazolyl-2)-propan-2-oles. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2012.01.015

文献信息

• Enzymatic Hydrolysis of Esters Containing a Tetrazole Ring
  作者：Edyta Łukowska-Chojnacka、Jolanta Mierzejewska

  DOI：10.1002/chir.22360

  日期：2014.12

  lipase‐catalyzed enantioselective hydrolysis of acetates containing tetrazole moiety was studied. Among all tested lipases, Novozyme SP 435 allowed to obtain optically active 4‐(5‐aryl‐2H‐tetrazol‐2yl)butan‐2‐ol and 1‐(5‐aryl‐2H‐tetrazol‐2yl)‐propan‐2‐ol and their acetates with the highest optical purities (ee = 95%‐99%) and excellent enantioselectivity (E>100). Some of the synthesized tetrazole derivatives were screened

  研究了脂肪酶催化的含有四唑部分的乙酸酯的对映选择性水解。在所有测试的脂肪酶中，Novozyme SP 435允许获得旋光的4-（5-芳基-2 H-四唑-2-基）丁烷-2-醇和1-（5-芳基-2 H-四唑-2基）丁烷。 2-ol及其乙酸酯具有最高的光学纯度（ee = 95％-99％）和出色的对映选择性（E> 100）。筛选了一些合成的四唑衍生物的抗真菌活性。的4- [5-（4-氯苯基）-2-外消旋混合物ħ -四唑-2-基）丁-2-醇，以及该化合物的纯对映体显示出有希望的对抗抗真菌活性˚F。接骨木，˚F。枯萎，Ç。coccodes，和一个。尼日尔。手性26：811–816，2014年。©2014 Wiley Periodicals，Inc.