4-bromotetrahydrothiopyran | 32358-88-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻烷
• 英文名称: 4-bromotetrahydrothiopyran
• 英文别名: 4-bromotetrahydro-2H-thiopyran；4-bromothiane
• CAS: 32358-88-6
• 化学式: C₅H₉BrS
• mdl: MFCD07357446
• 分子量: 181.096
• InChiKey: XYXKPHDVGJYKRH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  7
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  25.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4-bromotetrahydrothiopyran 在 magnesium 作用下， 以 乙醚 为溶剂， 以42%的产率得到4,4'-bis(tetrahydrothiopyranyl)
  参考文献：
  名称：

  Molecular and solid state structure of 4,4′-bis(tetrahydrothiopyranyl)

  摘要：

  Single crystal X-ray diffraction reveals that 4,4'-bis(tetrahydrothiopyranyl) crystallizes in an equatorial-equatorial geometry with a gauche conformation along the central carbon-carbon bond. B3LYP/6-311G** and MP2/6-311G** calculations show that the antiperiplanar conformation is higher in energy than the gauche one because of sulfur induced stretching and widening of the cyclohexane-like rings. Calculations at various levels of theory suggest that in the antiperiplanar region the twisting coordinate of 4,4'-bis(tetrahydrothiopyranyl) exhibits a very shallow double-well potential. The gauche molecular structure of 4,4'-bis(tetrahydrothiopyranyl) thwarts efficient packing of its molecules in the solid state. Crown Copyright 2012 Published by Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molstruc.2012.09.068
• 作为产物：
  描述：

  四氢噻喃-4-醇 在 三溴化磷 、 碳酸氢钠 作用下， 以 二氯甲烷 为溶剂， 以59%的产率得到4-bromotetrahydrothiopyran
  参考文献：
  名称：

  Molecular and solid state structure of 4,4′-bis(tetrahydrothiopyranyl)

  摘要：

  Single crystal X-ray diffraction reveals that 4,4'-bis(tetrahydrothiopyranyl) crystallizes in an equatorial-equatorial geometry with a gauche conformation along the central carbon-carbon bond. B3LYP/6-311G** and MP2/6-311G** calculations show that the antiperiplanar conformation is higher in energy than the gauche one because of sulfur induced stretching and widening of the cyclohexane-like rings. Calculations at various levels of theory suggest that in the antiperiplanar region the twisting coordinate of 4,4'-bis(tetrahydrothiopyranyl) exhibits a very shallow double-well potential. The gauche molecular structure of 4,4'-bis(tetrahydrothiopyranyl) thwarts efficient packing of its molecules in the solid state. Crown Copyright 2012 Published by Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molstruc.2012.09.068
• 作为试剂：
  描述：

  2-氯噻吨酮 在 4-bromotetrahydrothiopyran 、 magnesium 作用下， 生成 硫化环戊烷 、 阿奇霉素杂质B 、 2-Chloro-9-(4-tetrahydrothiopyranyl)thioxanthen-9-ol 、 4,4'-bis(tetrahydrothiopyranyl)
  参考文献：
  名称：

  Polivka, Zdenek; Holubek, Jiri; Budesinsky, Milos, Collection of Czechoslovak Chemical Communications, 1987, vol. 52, # 11, p. 2758 - 2774

  摘要：

  DOI：

文献信息

• Ni-Catalyzed Reductive Carbonylation of Alkyl Halides to Form Dialkyl Ketones Using Diphenyl Oxalate as CO Surrogate
  作者：Yuren Sun、Lei Su、Ken Yao、Hegui Gong、Weiqi Tong

  DOI：10.1055/a-1550-7935

  日期：2021.10

  In this work, we disclosed that diphenyl oxalate serves as a CO surrogate to enable a Ni-catalyzed carbonylation of alkyl bromides/tosylates to afford dialkyl ketones. The reaction shows broad substrate scope and good functional group tolerance.

  在这项工作中，我们公开了草酸二苯酯作为 CO 替代物，使 Ni 催化的烷基溴化物/甲苯磺酸盐羰基化得到二烷基酮。该反应显示出广泛的底物范围和良好的官能团耐受性。
• Group 14 Elements Hetero‐Difunctionalizations via Nickel‐Catalyzed Electroreductive Cross‐Coupling
  作者：Haifeng Chen、Chen Zhu、Huifeng Yue、Magnus Rueping

  DOI：10.1002/anie.202306498

  日期：2023.8.14

  A nickel-catalyzed three-components reductive protocol for the group 14 elements hetero-difunctionalizations via electrochemistry is described. The cascade reaction proceeded smoothly with the diverse chlorosilanes, 1,3-enynes, primary, secondary, and tertiary alkyl bromides. Good chemo- and regioselectivities were achieved. This protocol could be extended to germanyl- and stannylalkylation of 1,3-enynes

  描述了通过电化学进行 14 族元素异双官能化的镍催化三组分还原方案。多种氯硅烷、1,3-烯炔、伯、仲和叔烷基溴的级联反应顺利进行。实现了良好的化学和区域选择性。该方案可以扩展到 1,3-烯炔的锗基和甲锡烷基化，显示出其通用性和多功能性。
• Polivka, Zdenek; Budesinsky, Milos; Holubek, Jiri, Collection of Czechoslovak Chemical Communications, 1989, vol. 54, # 9, p. 2443 - 2469
  作者：Polivka, Zdenek、Budesinsky, Milos、Holubek, Jiri、Schneider, Bohdan、Sediva, Zdenek、et al.

  DOI：——

  日期：——
• POLIVKA, ZDENEK;PROTIVA, MIROSLAV;METYS, JAN
  作者：POLIVKA, ZDENEK、PROTIVA, MIROSLAV、METYS, JAN

  DOI：——

  日期：——
• POLIVKA, ZDENEK;BUDESINSKY, MILOS;HOLUBEK, JIRI;SCHNEIDER, BOHDAN;SEDIVY,+, COLLECT. CZECHOSL. CHEM. COMMUN., 54,(1989) N, C. 2443-2469
  作者：POLIVKA, ZDENEK、BUDESINSKY, MILOS、HOLUBEK, JIRI、SCHNEIDER, BOHDAN、SEDIVY,+

  DOI：——

  日期：——