5-异丙基-1,3,5-二噻嗪烷 | 34866-41-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氮杂环化合物
• 中文名称: 5-异丙基-1,3,5-二噻嗪烷
• 英文名称: 5-isopropyl-1,3,5-dithiazinane
• 英文别名: 5-isopropyl-1,3,5-dithiazine；5-Propan-2-yl-1,3,5-dithiazinane
• CAS: 34866-41-6
• 化学式: C₆H₁₃NS₂
• mdl: MFCD00955895
• 分子量: 163.308
• InChiKey: OBCQNGGOSQKNDR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  9
• 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

安全信息

• 海关编码：
  2934999090

反应信息

• 作为反应物：
  描述：

  5-异丙基-1,3,5-二噻嗪烷 在 叔丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 0.5h， 以100%的产率得到2-lithium-5-isopropyl-[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 、 异丙胺 在 sodium hydrogensulfide 作用下， 以 水 为溶剂， 反应 24.0h， 以70%的产率得到5-异丙基-1,3,5-二噻嗪烷
  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 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 Borane and Chloroborane Adducts of 1,3,5-Dithiaza-, -Dioxaza-, -Thiadiaza-, and -Triazacyclohexanes and Their Rearrangement Products, Boracyclohexanes
  作者：Angelina Flores-Parra、Sonia A. Sánchez-Ruíz、Carlos Guadarrama-Pérez

  DOI：10.1002/(sici)1099-0682(199911)1999:11<2063::aid-ejic2063>3.0.co;2-a

  日期：1999.11

  two-dimensional, and variable-temperature NMR spectroscopy of borane and chloroborane adducts of 1,3,5-heterocyclohexanes and their rearrangement products, boracyclohexanes, are reported. N-Methyl derivatives gave equatorial N-borane adducts whereas the N-isopropyl derivatives produced the axial borane compounds. Rearrangement reactions of the adducts gave the first examples of chloroboracyclohexanes bearing

  1,3,5-杂环己烷的硼烷和氯硼烷加合物及其重排产物硼环己烷的 1H-、11B-、13C-、二维和变温 NMR 光谱进行了结构和构象研究。N-甲基衍生物产生赤道N-硼烷加合物，而N-异丙基衍生物产生轴向硼烷化合物。加合物的重排反应给出了带有硼和氮原子作为稳定立体中心的氯硼环己烷的第一个例子。发现 BClH2 和 BCl2H 加合物对环重排比相应的 N-BH3 类似物更稳定。
• 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.
• New chiral heterocycles: 5-[(r)-(+)-1′-methylbenzyyl-1,3,5-dithiazine and 3-7-di-[(R)-(+)-1′-methylbenzyu-3-7-diaza-1,5-dithiacyclooctane. Conformational studies and their reactions with borane.
  作者：Gregorio Cadenas-Pliego、Maria de Jésus Rosales-Hoz、Rosalinda Contreras、Angelina Flores-Parra

  DOI：10.1016/0957-4166(94)80025-1

  日期：1994.4

  We report herein the syntheses of a new 5-[(R)-(+)-1'-methylbenzyl]-1,3,5-dithiazine 1, the 5-isopropyl-1,3,5-dithiazine 2 and the 3,7-di-[(R)-(+)-1'-methylbenzyl]-3,7-diaza-1,5-dithiacyclooctane 3, two of them (1 and 3) are new sulfur and nitrogen heterocycles bearing a chiral N-substituent. Compounds 1 and 2 were found in conformational equilibrium when observed at rt at H-1-270 MHz or C-13-67.8 MHz, when cooling a preferred chair conformation was observed with the N-substituent in the axial position. Heterocycle 3 was in an anchored crown conformation at rt. A conformational study of ring inversions for 1 and 3 was performed and their thermodynamic data were obtained, Delta G* = 48.1 +/- 0.8 for 1 and Delta G* = 64.8 +/- 1.2 kJ/mol for 3. The reactivity of 1-3 with BH3-THF was investigated, the N- or S-BH3 adducts were not stable, the reactions afforded cleanly the N-borane-N-dimethyl-N-alkylamine adducts. The reaction of 3 with BD3 gave the N-BD3 adduct of [CH2D]2N-CH[CH3]C6H5. An X-ray diffraction study of 3 confirmed its crown conformation with the N-substituents in pseudo-axial position.
• 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