5-(1-phenyl-1H-tetrazol-5-ylsulfanyl)pentan-1-ol

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-(1-phenyl-1H-tetrazol-5-ylsulfanyl)pentan-1-ol
• 英文别名: 5-[(1-phenyl-1H-tetrazol-5-yl)thio]pentan-1-ol；5-(1-Phenyltetrazol-5-yl)sulfanylpentan-1-ol
• 化学式: C₁₂H₁₆N₄OS
• mdl: MFCD17044154
• 分子量: 264.351
• InChiKey: FVKSJKPUERGFFM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.416
• 拓扑面积：
  89.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-(1-phenyl-1H-tetrazol-5-ylsulfanyl)pentan-1-ol 在 草酰氯 、 sodium hydride 、 二异丁基氢化铝 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 14.83h， 生成 (2E)-7-[(1-phenyl-1H-tetrazol-5-yl)thio]hept-2-en-1-ol
  参考文献：
  名称：

  Synthesis and Biological Properties of Novel Brefeldin A Analogues

  摘要：

  New brefeldin A (1) analogues were obtained by introducing a variety of substituents at C15. Most of the analogues exhibited significant biological activity. (15R)-Trifluoromethyl-nor-brefeldin A (3), (15R)-vinyl-nor-brefeldin A (5), their epimers 4 and 6 as well as (15S)-ethyl-nor-brefeldin A (2) were prepared from the key building blocks 12 or 24 by Julia-Kocienski olefination with tetrazolyl sulfones and subsequent macrolactonization. The vinyl derivative 5 allowed analogues to be synthesized by hydroboration and Suzuki-Miyaura coupling. The following biological properties were assessed: (a) inhibition of cell growth of human cancer cells (NCI), (b) induction of morphological changes of the Golgi apparatus of plant and mammalian cells, and (c) influence on the replication of the enterovirus CVB3. Furthermore, conformational aspects were studied by X-ray crystal structure analysis and molecular mechanics calculations, including docking of the analogues into the brefeldin A binding site of an Arf1/Sec7-complex.

  DOI：

  10.1021/jm400615g
• 作为产物：
  描述：

  1,5-戊二醇 、 1-苯基-5-巯基四氮唑 在 偶氮二甲酸二异丙酯 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 生成 5-(1-phenyl-1H-tetrazol-5-ylsulfanyl)pentan-1-ol
  参考文献：
  名称：

  Enantioselective Formal Synthesis of Brefeldin A and Analogues via Anionic Cyclization of an Alkenyl Epoxide

  摘要：

  通过烯基环氧化物的环氧腈环化制备了适合作为合成布雷菲德菌素 A 和类似物 6,7-脱氢布雷菲德菌素 C 和降布雷菲德菌素 A 的中间体的环戊烯衍生物。

  DOI：

  10.1055/s-2006-941575

文献信息

• A direct and efficient preparation of 1-phenyltetrazol-5-yl sulfides from alcohols
  作者：Adam R. Ellwood、Michael J. Porter

  DOI：10.1039/c0ob00863j

  日期：——

  Treatment of primary or secondary alcohols with 1-phenyl-1(H)-tetrazole-5-thiol and [Me2NCHSEt]+ BF4− leads directly and cleanly to 1-phenyl-1(H)-tetrazol-5-yl sulfides.

  用 1-苯基-1(H)-四唑-5-硫醇和 [Me2NCHSEt]+ BF4- 处理伯醇或仲醇，可直接生成 1-苯基-1(H)-四唑-5-基硫化物。
• Enantioselective Formal Synthesis of Brefeldin A and Analogues via Anionic Cyclization of an Alkenyl Epoxide
  作者：Günter Helmchen、Tina Hübscher

  DOI：10.1055/s-2006-941575

  日期：2006.6

  Cyclopentene derivatives suitable as intermediates for syntheses of brefeldin A and analogues 6,7-dehydrobrefeldin C and norbrefeldin A were prepared by epoxynitrile cyclization of alkenyl epoxides.

  通过烯基环氧化物的环氧腈环化制备了适合作为合成布雷菲德菌素 A 和类似物 6,7-脱氢布雷菲德菌素 C 和降布雷菲德菌素 A 的中间体的环戊烯衍生物。
• Synthesis and Biological Properties of Novel Brefeldin A Analogues
  作者：Kai Seehafer、Frank Rominger、Günter Helmchen、Markus Langhans、David G. Robinson、Başak Özata、Britta Brügger、Jeroen R. P. M. Strating、Frank J. M. van Kuppeveld、Christian D. Klein

  DOI：10.1021/jm400615g

  日期：2013.7.25

  New brefeldin A (1) analogues were obtained by introducing a variety of substituents at C15. Most of the analogues exhibited significant biological activity. (15R)-Trifluoromethyl-nor-brefeldin A (3), (15R)-vinyl-nor-brefeldin A (5), their epimers 4 and 6 as well as (15S)-ethyl-nor-brefeldin A (2) were prepared from the key building blocks 12 or 24 by Julia-Kocienski olefination with tetrazolyl sulfones and subsequent macrolactonization. The vinyl derivative 5 allowed analogues to be synthesized by hydroboration and Suzuki-Miyaura coupling. The following biological properties were assessed: (a) inhibition of cell growth of human cancer cells (NCI), (b) induction of morphological changes of the Golgi apparatus of plant and mammalian cells, and (c) influence on the replication of the enterovirus CVB3. Furthermore, conformational aspects were studied by X-ray crystal structure analysis and molecular mechanics calculations, including docking of the analogues into the brefeldin A binding site of an Arf1/Sec7-complex.