2-硫杂三环(3.3.1.1(3,7))癸烷 | 281-25-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻烷
• 中文名称: 2-硫杂三环(3.3.1.1(3,7))癸烷
• 英文名称: 2-Thia-adamantan
• 英文别名: 2-Thiaadamantane；2-thiatricyclo[3.3.1.13,7]decane
• CAS: 281-25-4
• 化学式: C₉H₁₄S
• 分子量: 154.276
• InChiKey: NOBCRSKNBOQNEL-UHFFFAOYSA-N

物化性质

• 保留指数：
  1429;1439;1449

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  4.0
• 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：

  2-硫杂三环(3.3.1.1(3,7))癸烷 在 Oxone 、 potassium sulfate 、 potassium hydrogensulfate 、 oxone 作用下， 以 甲醇 、 丙酮 为溶剂， 反应 0.17h， 以95%的产率得到2-Thia-tricyclo[3.3.1.1^3,7]decane 2-oxide
  参考文献：
  名称：

  On the stereochemistry of the oxidation of 5-phenyl-2-thiaadamantane

  摘要：

  DOI：

  10.1021/jo00079a056
• 作为产物：
  描述：

  3,7-Diiodobicyclo<3.3.1>nonane 在 sodium sulfide 作用下， 以 乙醇 为溶剂， 反应 10.0h， 以40%的产率得到2-硫杂三环(3.3.1.1(3,7))癸烷
  参考文献：
  名称：

  The Replacement of the Carbonyl Group of Adamantanone by an Oxygen or Sulfur Atom and the One-step Transformation of 2-Methyladamantan-2-ol into 2-Oxa-adamantane; An Efficient New Synthesis of 2-Oxa- and 2-Thiaadamantane

  摘要：

  2- 氧杂金刚烷有两种制备方法：以金刚烷酮为原料，通过拜耳-维里格氧化、还原或还原甲基化、环裂碘化和再化学反应四步顺序制备；或以 2-甲基-2-金刚烷醇为原料，通过不分离中间产物的两步反应制备。与此相关，2-thiaadamantane 是由金刚烷酮通过五步反应制备而成，包括拜耳-维里格氧化反应、还原甲基化反应、环裂碘化反应、进一步碘化反应以及 3,7-二碘双环[3.3.1]壬烷与硫化钠的环缩合反应。

  DOI：

  10.1055/s-1986-31761

文献信息

• Sulfur Compounds in Kerosine Boiling Range of Middle East Crudes
  作者：S. F. Birch、T. V. Cullum、R. A. Dean、R. L. Denyer

  DOI：10.1021/ie50542a027

  日期：1955.2
• SUGINOME HIROSHI; YAMADA SHINJI, SYNTHESIS,(1986) N 9, 741-743
  作者：SUGINOME HIROSHI、 YAMADA SHINJI

  DOI：——

  日期：——
• The determination of sulfoxide configuration in six-membered rings using NMR spectroscopy and DFT calculations
  作者：M. Dračínský、R. Pohl、L. Slavětínská、J. Janků、M. Buděšínský

  DOI：10.1016/j.tetasy.2011.02.001

  日期：2011.2

  Cyclic six-membered ring sulfoxides and sulfones were prepared by a stepwise in situ oxidation of the corresponding sulfides with meta-chloroperbenzoic acid in an NMR tube. The oxidation was followed by NMR spectra and the H-1 and C-13 NMR data were collected. The geometries of all of the compounds were optimized using the DFT B3LYP/6-31G** method and the C-13 and H-1 NMR chemical shifts were calculated for geometry-optimized structures with the DFT B3LYP/6-31++G** method. The calculated C-13 NMR chemical shifts induced by oxidation (Delta delta values) are in very good agreement with the experimental data and can be used to determine the oxidation state of the sulfur atom (-S-, -SO-, -SO2-). The characteristic differences of the induced oxidation chemical shifts of carbon atoms at the alpha- and beta-position to sulfur were successfully used for distinguishing between the diastereoisomeric sulfoxides. (C) 2011 Elsevier Ltd. All rights reserved.
• The Replacement of the Carbonyl Group of Adamantanone by an Oxygen or Sulfur Atom and the One-step Transformation of 2-Methyladamantan-2-ol into 2-Oxa-adamantane; An Efficient New Synthesis of 2-Oxa- and 2-Thiaadamantane
  作者：Hiroshi Suginome、Shinji Yamada

  DOI：10.1055/s-1986-31761

  日期：——

  2-Oxaadamantane is prepared by two methods: From adamantanone by a four-step sequence consisting of Baeyer-Villiger oxidation, reduction or reductive methylation, iodination with ring cleavage, and recyclization, or from 2-methyl-2-adamantanol by a two-step reaction without isolation of intermediates. In a related manner, 2-thiaadamantane is prepared from adamantanone by a five-step sequence consisting of Baeyer-Villiger oxidation, reductive methylation, iodination with ring cleavage, further iodination, and cyclocondensation of 3,7-diiodobicyclo[3.3.1]nonane with sodium sulfide.

  2- 氧杂金刚烷有两种制备方法：以金刚烷酮为原料，通过拜耳-维里格氧化、还原或还原甲基化、环裂碘化和再化学反应四步顺序制备；或以 2-甲基-2-金刚烷醇为原料，通过不分离中间产物的两步反应制备。与此相关，2-thiaadamantane 是由金刚烷酮通过五步反应制备而成，包括拜耳-维里格氧化反应、还原甲基化反应、环裂碘化反应、进一步碘化反应以及 3,7-二碘双环[3.3.1]壬烷与硫化钠的环缩合反应。
• On the stereochemistry of the oxidation of 5-phenyl-2-thiaadamantane
  作者：Ashis K. Mukherjee、William J. le Noble

  DOI：10.1021/jo00079a056

  日期：1993.12

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