(5-methyl-1,3,5-dithiaazacyclohexane)(borane) | 137425-60-6

• 英文名称: (5-methyl-1,3,5-dithiaazacyclohexane)(borane)
• 英文别名: 5-methyl-1,3,5-dithiazinane-5-borane；5-methyl-1,3,5-dithiazin-5-borane
• CAS: 137425-60-6
• 化学式: C₄H₁₂BNS₂
• 分子量: 149.089
• InChiKey: NVWMFXLBLBQYHJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
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• 重原子数：
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• 可旋转键数：
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• 环数：
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• sp3杂化的碳原子比例：
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• 拓扑面积：
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• 氢给体数：
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• 氢受体数：
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反应信息

• 作为反应物：
  描述：

  (5-methyl-1,3,5-dithiaazacyclohexane)(borane) 以 四氢呋喃 为溶剂， 生成 5,5-dimethyl-1,3-dithia-5-azonia-4-boratacyclohexane
  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：

  二氢-5-甲基-4H-1,3,5-二噻嗪 在 dimethyl sulfide borane 作用下， 以 四氢呋喃 为溶剂， 生成 (5-methyl-1,3,5-dithiaazacyclohexane)(borane)
  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

• 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.
• Flores-Parra, Angelina; Cadenas-Pliego, Gregorio; Martinez-Aguilera, Luz Maria R., Chemische Berichte, 1993, vol. 126, # 4, p. 863 - 868
  作者：Flores-Parra, Angelina、Cadenas-Pliego, Gregorio、Martinez-Aguilera, Luz Maria R.、Garcia-Nares, M. Lourdes、Contreras, Rosalinda

  DOI：——

  日期：——
• 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.