methoxycarbonylsulfanyl isocyanate | 958004-30-3

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫代羰基化合物
• 英文名称: methoxycarbonylsulfanyl isocyanate
• 英文别名: CH₃OC(O)SNCO；methoxycarbonylsulfenyl isocyanate；Methyl isocyanatosulfanylformate
• CAS: 958004-30-3
• 化学式: C₃H₃NO₃S
• 分子量: 133.128
• InChiKey: NVLQBZWAXQIIAT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  8
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  81
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methoxycarbonylsulfanyl isocyanate 在 重水 、 silver(I) chloride 作用下， 生成 1,3-bis((methoxycarbonyl)thio)urea-d2
  参考文献：
  名称：

  Structural effects and hydrogen bonds on N,N′-di(methoxycarbonylsulfenyl)urea, [CH3OC(O)SNH]2CO, studied by experimental and theoretical methods

  摘要：

  Pure N,N'-di(methoxycarbonylsulfenyl)urea, [CH3OC(O)SNH](2)CO, is quantitatively prepared by the hydrolysis reaction of CH3OC(O)SNCO and characterized by H-1 NMR, GC-MS and FTIR spectroscopy techniques. Structural and conformational properties are analyzed using a combined approach with data obtained from X-ray diffraction, vibrational spectra and theoretical calculation methods. The IR and Raman spectra for normal and deuterated species are reported. The crystal structure of [CH3OC(O)SNH](2)CO was determined by X-ray diffraction methods. The substance crystallizes in the orthorhombic P2(1)2(1)2 space group with a = 9.524(2), b = 12.003(1), c = 4.481 (1) angstrom, and Z = 2 moieties in the unit cell. The molecule is sited on a twofold crystallographic axis (C-2) parallel to c and shows the anti-anti conformation (S-N single bonds antiperiplanar with respect to the opposite C-N single bonds in sulfenyl-urea-sic group). Neighboring molecules are arranged in a chain motif that extends along the C-2-axis and is held by bifurcated NH center dot center dot center dot O center dot center dot center dot HN intermolecular bonds. A local planar symmetry is observed in the crystal for the central -SN(H)C(O)N(H)S- skeleton. Experimental and calculated data allow to trace this structural feature to the occurrence of N-H center dot center dot center dot O=C hydrogen bonding interactions. Calculated vibrational and structural properties are in good agreement with the experimentally determined features. (C) 2008 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molstruc.2008.07.031
• 作为产物：
  描述：

  氯化甲氧羰基硫 、 silver cyanate 反应 2.0h， 生成 methoxycarbonylsulfanyl isocyanate
  参考文献：
  名称：

  甲氧基羰基亚硫基异氰酸酯CH 3 OC（O）SNCO的制备与性能

  摘要：

  通过CH 3 OC（O）SCl与AgNCO的复分解反应定量制备纯甲氧基羰基亚硫基异氰酸酯CH 3 OC（O）SNCO。这种新颖的物种已以其纯净形式获得，并通过1 H和13 C NMR，UV-vis，FTIR和FT-Raman光谱进行了表征。气态分子的构象性质已通过振动光谱和量子化学计算（B3LYP和MP2方法）进行了研究。该化合物在室温下显示构象平衡，具有最稳定的C S对称性，与C对称相对于SN单键为O双键同上平面。在IR光谱中观察到第二种形式，其对应于相对于异氰酸酯基团的N C双键具有反平面的CS键的构象异构体。CH 3 OC（O）SNCO的单晶结构是通过使用微型区熔融程序在低温下通过X射线衍射分析确定的。结晶固体（三斜晶系，P 1，一个= 8.292（6），b = 9.839（7），C ^ = 11.865（8）埃，α= 67.290（2）°，β= 71.5570（10）°，γ = 83

  DOI：

  10.1021/jo701543g

文献信息

• Convenient synthesis of carbamates, S-alkyl thiocarbamates, and N,N′-disubstituted urea derivatives of methoxycarbonylsulfenyl isocyanate
  作者：Sonia Torrico-Vallejos、Mauricio F. Erben、Evamarie Hey-Hawkins、Carlos O. Della Védova

  DOI：10.1016/j.tetlet.2011.08.027

  日期：2011.10

  methods for the synthesis of carbamates, N,N′-unsymmetrically disubstituted ureas, and S-alkyl thiocarbamates derived from CH3OC(O)SNCO in one-step are provided. Reactions are operationally simple and have high selectivity toward nitrogen, oxygen, and sulfur nucleophiles. The absence of solvents coupled with high yields and short reaction times make these procedures very attractive for synthesis.

  提供了一种方便，简单，合适的方法，可一步合成合成氨基甲酸酯，N，N'-不对称双取代尿素和CH 3 OC（O）SNCO衍生的S-烷基硫代氨基甲酸酯。反应操作简单，对氮，氧和硫亲核试剂具有高选择性。缺少溶剂，再加上高产率和短反应时间，使得这些方法对于合成非常有吸引力。
• Crystal structure and spectroscopic properties of N′-methoxycarbonylsulfenyl-substituted ureas, CH3OC(O)SN(H)C(O)NRR′ [R=H, R′=C(CH3)3 and R=R′=CH2CH3]
  作者：Sonia Torrico-Vallejos、Mauricio F. Erben、Santiago Gómez Ruiz、Evamarie Hey-Hawkins、Gustavo A. Echeverría、Oscar E. Piro、Carlos O. Della Védova

  DOI：10.1016/j.molstruc.2012.12.047

  日期：2013.4

  Structural and spectroscopic properties of N,N-diethyl- (I) and N-tert-butyl-N'-methoxycarbonylsulfenyl urea (II) are analyzed using a combined approach with data obtained from X-ray diffraction, vibrational spectra and quantum chemical calculations. The molecular structures of CH3OC(O)SN(H)C(O)N(CH2CH3)(2) (I) and CH3OC(O)SN(H)C(O)N(H)C(CH3)(3) (II), the later co-crystallized with ethyl acetate (II 1/2EtOAc), were determined by X-ray diffraction methods. Compound I crystallizes in the triclinic space group P-1 and II.0.5EtOAc in the orthorhombic space group Pnma. In I, there are two independent but closely related molecules in the asymmetric unit whose conformations differ only in the orientation of the terminal N(CH2CH3)(2) groups. Neighboring molecules in I exhibit N-H center dot center dot center dot O interaction giving rise to a polymeric chains. The conformation of the O-C=O-S-N-C=O-N skeleton of II is almost identical to the corresponding one of both molecules of I. Neighboring molecules in II are linked through bifurcated N-H center dot center dot center dot O center dot center dot center dot H-N interactions giving rise to a polymeric chain. The vibrational properties have been studied by FTIR and FT-Raman spectroscopy along with quantum chemical calculations at the B3LYP/6-311+G* level. (C) 2013 Published by Elsevier B.V.
• Preparation and Properties of Methoxycarbonylsulfenyl Isocyanate, CH₃OC(O)SNCO
  作者：Sonia Torrico Vallejos、Mauricio F. Erben、Helge Willner、Roland Boese、Carlos O. Della Védova

  DOI：10.1021/jo701543g

  日期：2007.11.1

  Pure methoxycarbonylsulfenyl isocyanate, CH3OC(O)SNCO, is quantitatively prepared by the metathesis reaction between CH3OC(O)SCl and AgNCO. This novel species has been obtained in its pure form and characterized by 1H and 13C NMR, UV−vis, FTIR, and FT-Raman spectroscopy. The conformational properties of the gaseous molecule have been studied by vibrational spectroscopy and quantum chemical calculations

  通过CH 3 OC（O）SCl与AgNCO的复分解反应定量制备纯甲氧基羰基亚硫基异氰酸酯CH 3 OC（O）SNCO。这种新颖的物种已以其纯净形式获得，并通过1 H和13 C NMR，UV-vis，FTIR和FT-Raman光谱进行了表征。气态分子的构象性质已通过振动光谱和量子化学计算（B3LYP和MP2方法）进行了研究。该化合物在室温下显示构象平衡，具有最稳定的C S对称性，与C对称相对于SN单键为O双键同上平面。在IR光谱中观察到第二种形式，其对应于相对于异氰酸酯基团的N C双键具有反平面的CS键的构象异构体。CH 3 OC（O）SNCO的单晶结构是通过使用微型区熔融程序在低温下通过X射线衍射分析确定的。结晶固体（三斜晶系，P 1，一个= 8.292（6），b = 9.839（7），C ^ = 11.865（8）埃，α= 67.290（2）°，β= 71.5570（10）°，γ = 83
• Structural effects and hydrogen bonds on N,N′-di(methoxycarbonylsulfenyl)urea, [CH3OC(O)SNH]2CO, studied by experimental and theoretical methods
  作者：Sonia Torrico Vallejos、Mauricio F. Erben、Roland Boese、Oscar E. Piro、Eduardo E. Castellano、Carlos O. Della Védova

  DOI：10.1016/j.molstruc.2008.07.031

  日期：2009.1

  Pure N,N'-di(methoxycarbonylsulfenyl)urea, [CH3OC(O)SNH](2)CO, is quantitatively prepared by the hydrolysis reaction of CH3OC(O)SNCO and characterized by H-1 NMR, GC-MS and FTIR spectroscopy techniques. Structural and conformational properties are analyzed using a combined approach with data obtained from X-ray diffraction, vibrational spectra and theoretical calculation methods. The IR and Raman spectra for normal and deuterated species are reported. The crystal structure of [CH3OC(O)SNH](2)CO was determined by X-ray diffraction methods. The substance crystallizes in the orthorhombic P2(1)2(1)2 space group with a = 9.524(2), b = 12.003(1), c = 4.481 (1) angstrom, and Z = 2 moieties in the unit cell. The molecule is sited on a twofold crystallographic axis (C-2) parallel to c and shows the anti-anti conformation (S-N single bonds antiperiplanar with respect to the opposite C-N single bonds in sulfenyl-urea-sic group). Neighboring molecules are arranged in a chain motif that extends along the C-2-axis and is held by bifurcated NH center dot center dot center dot O center dot center dot center dot HN intermolecular bonds. A local planar symmetry is observed in the crystal for the central -SN(H)C(O)N(H)S- skeleton. Experimental and calculated data allow to trace this structural feature to the occurrence of N-H center dot center dot center dot O=C hydrogen bonding interactions. Calculated vibrational and structural properties are in good agreement with the experimentally determined features. (C) 2008 Elsevier B.V. All rights reserved.