5-tert-butyl-1,3,5-dithiazinane | 34866-42-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氮杂环化合物
• 英文名称: 5-tert-butyl-1,3,5-dithiazinane
• CAS: 34866-42-7
• 化学式: C₇H₁₅NS₂
• 分子量: 177.335
• InChiKey: QPQICTWOSDRHIA-UHFFFAOYSA-N

物化性质

• 沸点：
  243.2±30.0 °C(Predicted)
• 密度：
  1.089±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  53.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-tert-butyl-1,3,5-dithiazinane 在 叔丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 0.5h， 以0.33 g的产率得到5-tert-butyl-2-lithium-[1,3,5]dithiazinane
  参考文献：
  名称：

  Mono- and di-alkyl-[1,3,5]-dithiazinanes and their N–borane adducts revisited. Structural and theoretical study

  摘要：

  Structural analyses of a series of 5-alkyl-[1,3,5]-dithiazinanes [R = Me (1), iPr (2), tBu (3)], their N-BH3 adducts (1BH(3)-3BH(3)) and their 2-alkyl (R') derivatives are reported: R = Me, R' = Me (7); R = Me, R' iPr (8); R = iPr, R' = Me (10); R = tBu, R' = Me (11); and R = Me, R' = nBu (12). The reaction of 2-lithium-5-methyl-[1,3,5]-dithiazinane (4) with I-2 affords the bis-(5-methyl-[1,3,5]-dithiazinan-2-yl) (13). Isostructural compounds: [2,5,5]-trimethyl-[1,3,5]-dithiazinan-5-ium iodide (14), 5-borane-2,5-dimethyl-[1,3,5]-dithiazinane (15) and 2,5,5-trimethyl[1,3,5,6]-dithiazaborata (16) are compared. Structures of 7,8 and 10-13 were determined by B-11, C-13 and H-1 NMR and the X-ray diffraction analyses of 2, 1BH(3), 13 and 14 are reported. Optimization of two chair conformers of heterocycles 1-3,1BH(3)-3BH(3), 7, 9 (R = Me, R' = tBu), 13-16 were performed by HF/6-31++G and B3LYP/6-31G(d,p) methods and their minimum energy is compared. 2-Alkyl substituents or N-BH3 anchor the [1,3,5]-dithiazinane ring conformation allowing the analyses of steric and electronic interactions as well as the lone pairs effect in these molecules. (C) 2013 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molstruc.2013.04.021
• 作为产物：
  描述：

  聚合甲醛 、 叔丁胺 在 sodium hydrogensulfide 作用下， 以 水 为溶剂， 反应 24.0h， 生成 5-tert-butyl-1,3,5-dithiazinane
  参考文献：
  名称：

  Mono- and di-alkyl-[1,3,5]-dithiazinanes and their N–borane adducts revisited. Structural and theoretical study

  摘要：

  Structural analyses of a series of 5-alkyl-[1,3,5]-dithiazinanes [R = Me (1), iPr (2), tBu (3)], their N-BH3 adducts (1BH(3)-3BH(3)) and their 2-alkyl (R') derivatives are reported: R = Me, R' = Me (7); R = Me, R' iPr (8); R = iPr, R' = Me (10); R = tBu, R' = Me (11); and R = Me, R' = nBu (12). The reaction of 2-lithium-5-methyl-[1,3,5]-dithiazinane (4) with I-2 affords the bis-(5-methyl-[1,3,5]-dithiazinan-2-yl) (13). Isostructural compounds: [2,5,5]-trimethyl-[1,3,5]-dithiazinan-5-ium iodide (14), 5-borane-2,5-dimethyl-[1,3,5]-dithiazinane (15) and 2,5,5-trimethyl[1,3,5,6]-dithiazaborata (16) are compared. Structures of 7,8 and 10-13 were determined by B-11, C-13 and H-1 NMR and the X-ray diffraction analyses of 2, 1BH(3), 13 and 14 are reported. Optimization of two chair conformers of heterocycles 1-3,1BH(3)-3BH(3), 7, 9 (R = Me, R' = tBu), 13-16 were performed by HF/6-31++G and B3LYP/6-31G(d,p) methods and their minimum energy is compared. 2-Alkyl substituents or N-BH3 anchor the [1,3,5]-dithiazinane ring conformation allowing the analyses of steric and electronic interactions as well as the lone pairs effect in these molecules. (C) 2013 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molstruc.2013.04.021

文献信息

• Synthesis, crystal structure, and interconversions of new N-aryl-1,3,5-dithiazinanes, 1,3,5-thiadiazinanes, and 1,5-dithia-3,7-diazacyclooctanes
  作者：V. R. Akhmetova、Z. T. Niatshina、G. R. Khabibullina、I. S. Bushmarinov、A. O. Borisova、Z. A. Starikova、L. F. Korzhova、R. V. Kunakova

  DOI：10.1007/s11172-010-0196-y

  日期：2010.5

  mixture in the synthesis of N-aryl-substituted 1,3,5-dithiazinanes, 1,3,5-thiadiazinanes, and 1,5-dithia-3,7-diazacyclooctanes has been studied depending on the type and mutual arrangement of substituents in the starting anilines, ratio of reagents, temperature, and reaction time. Conformation of the synthesized heterocycles in crystal has been found by X-ray diffraction. Interconversion of the heterocycles

  苯胺与 CH2O-H2S 硫甲基化混合物在合成 N-芳基取代的 1,3,5-二噻嗪、1,3,5-噻二嗪和 1,5-二噻-3,7-二氮杂环辛烷中的多组分反应的化学选择性已根据起始苯胺中取代基的类型和相互排列、试剂比例、温度和反应时间进行了研究。已通过 X 射线衍射发现晶体中合成杂环的构象。杂环的相互转化显示了 N-芳基-1,3,5-二噻嗪烷的稳定性。
• Preparation, Structure, and Unique Redox Properties of Mono-, Bis-, and Tris(diarylmethylene)-1,3,5-trithianes and Related Compounds
  作者：Takanori Suzuki、Tsuyoshi Yoshino、Jun-ichi Nishida、Masakazu Ohkita、Takashi Tsuji

  DOI：10.1021/jo000161l

  日期：2000.9.1

  that a large structural change and/or transannular bonding are induced during their electrochemical oxidation. Mono(diarylmethylene) derivative 1a exhibits electrochromism with vivid change in color from faintly yellow to deep blue with concomitant rotation around the exocyclic bond. Both of the strongly colored salts obtained upon oxidation of 2,4-bis- and 2,4,6-tris(diarylmethylene)-1,3,5-trithianes

  设计了一系列具有二芳基亚甲基单元的1,3,5-三噻烷1-3，作为新型电子给体，在氧化时可得到高度着色的阳离子。它们与二噻吩和二噻嗪衍生物4-6一起通过锂化杂环与二芳基酮的反应然后脱水来制备。伏安分析表明，在其电化学氧化过程中会引起大的结构变化和/或跨环键。单（二芳基亚甲基）衍生物1a表现出电致变色，其颜色从淡黄色变为深蓝色，伴随着围绕环外键的旋转。2,4-双-和2,4,6-三（二芳基亚甲基）-1,3,5-三噻烷（2aa和3）氧化后得到的两种强烈着色的盐均含有1,2， 4-三硫环 提示具有三噻吩并[3.1.0]己烷环的跨环药物容易发生骨骼重排。还原这些盐后，分别得到亮黄色12和13，由于四芳基丁二烯型共轭，具有高供电子性，从而得到另一类电致变色化合物。
• Synthesis and structural study of bis-, tris- and tetra-[1,3,5]-dithiazinanyl silanes and stannanes
  作者：Pedro Montes-Tolentino、Raúl Colorado-Peralta、Luis A. Martínez-Chavando、Edgar Mijangos、Angélica M. Duarte-Hernández、Galdina V. Suárez-Moreno、Rosalinda Contreras、Angelina Flores-Parra

  DOI：10.1016/j.jorganchem.2013.07.060

  日期：2014.2

  The synthesis and structural study of 23 new bis-, tris-, tetra-(dithiazinan-2-yl)silanes and stannanes is reported. The compounds were obtained by reaction of 5-alkyl-[1,3,5]-dithiazinanes (alkyl = Me, iPr, tBu) with tBuLi followed by addition of R′nSiCl4−n or R′nSnCl4−n (n = 0–2, R′ = Me and Ph) in THF. Structures were determined by 1H, 13C, 29Si or 119Sn NMR, mass spectrometry and X-ray diffraction

  报道了23种新的双-，三-，四-（二噻唑烷-2-基）硅烷和锡烷的合成和结构研究。由5 -烷基- [1,3,5] -dithiazinanes（烷基= Me中，反应得到的化合物我PR，吨卜）与吨丁基锂，然后加入R'的ñ的SiCl 4- Ñ或R' ñ的SnCl 在THF中为4- n（n = 0–2，R'= Me和Ph）。结构由1 H，13 C，29 Si或119确定Sn NMR，质谱和X射线衍射分析。讨论了固态化合物的构象。硅烷基和锡烷基在溶液中的双和三-二噻唑烷基化合物中处于赤道位置。的X射线衍射四- （ñ -异丙基dithiazinan -2-基）锡烷表明，锡原子被轴向键结合到由赤道键2个dithiazinanyl基和另外两个。原子距离表示硫硅和硫锡短接点。NMR数据，尤其是29 Si和119 SN化学位移和1 J（13 C，119Sn）耦合常数表明化合物中存在弱的S⋯Si和S⋯Sn相互作
• Structural analyses of 2-triorganylsilyl- and 2-triorganylstannyl derivatives of 5-alkyl-[1,3,5]-dithiazinanes. Do S⋯Si and S⋯Sn interactions exist?
  作者：Raúl Colorado-Peralta、Carlos Guadarrama-Pérez、Luis A. Martínez-Chavando、Juan Carlos Gálvez-Ruiz、Angélica M. Duarte-Hernández、Galdina V. Suárez-Moreno、Aurora Vásquez-Badillo、Sonia A. Sánchez-Ruiz、Rosalinda Contreras、Angelina Flores-Parra

  DOI：10.1016/j.jorganchem.2013.07.058

  日期：2014.2

  A series of 2 - R-3'E (E = Si or Sn; R' = Me or Ph) derivatives of 5-R-[1,3,5]-dithiazinanes (R = Me, iPr, tBu) are reported, as well as some of their N-BH3 adducts. Structures were determined by Si-29, Sn-119, B-11, C-13 and H-1 NMR and X ray diffraction analyses. Minimum energy conformations were calculated by HF/631++G(d,p) and B3LYP/6-31++G(d,p) methods. Preferred conformations and steric and stereo-electronic interactions are analyzed. In the solid state the ring conformation is a chair with the N-R group in axial and the 2-substituents in equatorial position. The Si or Sn atoms linked to C-2 have short distances to the two sulfur atoms, interpreted as Si center dot center dot center dot S and Sn center dot center dot center dot S stabilizing contacts. The Sn-119 NMR chemical shifts and (1)J(C-13, Sn-119) coupling constants evidenced weak S center dot center dot center dot Sn coordination bonds. Substitution reactions at C2 performed in N-BH3 adducts of 2-lithium-5-methyl-[1,3,5]-dithiazinanes of anchored conformation proceed with retention of C2 configuration. (c) 2013 Elsevier B.V. All rights reserved.
• Sodium Sulfide in the Synthesis of N-Alkyl-1,3,5-dithiazinanes and 1,3,5-Thiadiazinanes
  作者：G. R. Khabibullina、D. K. Yapparova、A. G. Ibragimov、V. R. Akhmetova

  DOI：10.1134/s1070363221080053

  日期：2021.8