2,5-Dimethyl-5-aza-1,3-dithiacyclohexane | 122470-99-9

• 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: 2,5-Dimethyl-5-aza-1,3-dithiacyclohexane
• 英文别名: 2,5-dimethyl-1,3,5-dithiazacyclohexane；2,5-dimethyl-1,3,5-dithiazine；2-methyl-[1,3,5]dithiazinane；2,5-Dimethyl-1,3,5-dithiazinane
• CAS: 122470-99-9
• 化学式: C₅H₁₁NS₂
• 分子量: 149.281
• InChiKey: HOJWJBDKYJIESG-UHFFFAOYSA-N

物化性质

• 沸点：
  212.7±30.0 °C(Predicted)
• 密度：
  1.093±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  8
• 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：
  53.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,5-Dimethyl-5-aza-1,3-dithiacyclohexane 在 dimethyl sulfide borane 、 氯硼烷 、 二氯硼 作用下， 以 二氯甲烷 为溶剂， 反应 8.0h， 生成
  参考文献：
  名称：

  1,3,5-二噻氮杂-、-二恶氮杂-、-噻二氮杂-和-三氮杂环己烷的硼烷和氯硼烷加合物及其重排产物、硼环己烷的结构分析

  摘要：

  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。

  DOI：

  10.1002/(sici)1099-0682(199911)1999:11<2063::aid-ejic2063>3.0.co;2-a
• 作为产物：
  描述：

  二氢-5-甲基-4H-1,3,5-二噻嗪 、 碘甲烷 在 正丁基锂 作用下， 生成 2,5-Dimethyl-5-aza-1,3-dithiacyclohexane
  参考文献：
  名称：

  The existence of second-row anomeric interactions. Conformational analysis of 2-substituted 5-methyl-5-aza-1,3-dithiacyclohexanes

  摘要：

  DOI：

  10.1021/ja00199a038

文献信息

• Mono- and di-alkyl-[1,3,5]-dithiazinanes and their N–borane adducts revisited. Structural and theoretical study
  作者：Angelina Flores-Parra、Carlos Guadarrama-Pérez、Juan Carlos Gálvez Ruiz、Sonia A. Sánchez Ruiz、Galdina V. Suarez-Moreno、Rosalinda Contreras

  DOI：10.1016/j.molstruc.2013.04.021

  日期：2013.9

  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.
• A New Lithium 5‐Methyl‐1,3‐dithia‐5‐azacyclohex‐2‐ylborate —5‐Borane and Two Dimeric 5‐Methyl‐1,3‐dithia‐5‐azacyclohex‐2‐yllithium Compounds — Stereochemistry and Reactivity
  作者：Carlos Guadarrama‐Pérez、Gregorio Cadenas‐Pliego、Luz Maria R. Martínez‐Aguilera、Angelina Flores‐Parra

  DOI：10.1002/cber.19971300622

  日期：1997.6

  AbstractSyntheses of the dimers of axial 5‐methyl‐2‐dithiazinyllithium (4) and equatorial 5‐methyl‐2‐diethiazinyllithium‐5‐borane (5), and lithium 5‐methyl‐2‐dithiazinanylborate‐5‐borane (6) are reported. Compounds 4, 5, and 6 are configurationally and conformationally stable. The 1H‐, 13H‐, 13C‐, 11B‐, and 7Li‐NMR study of th reactions of 4 and 5 with BH3S(CH3)2, BH3—THF, and CH3I is presented.
• The existence of second-row anomeric interactions. Conformational analysis of 2-substituted 5-methyl-5-aza-1,3-dithiacyclohexanes
  作者：Eusebio Juaristi、Eduardo A. Gonzalez、B. Mario Pinto、Blair D. Johnston、Ruby Nagelkerke

  DOI：10.1021/ja00199a038

  日期：1989.8
• 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。