2-trimethylsiloxycarbonyl-3-trimethylsiloxynaphthalene | 372980-41-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-trimethylsiloxycarbonyl-3-trimethylsiloxynaphthalene
• 英文别名: trimethylsilyl 3-((trimethylsilyl)oxy)-2-naphthoate；2-Trimethyl-siloxycarbonyl-3-trimethylsiloxynaphthalene；trimethylsilyl 3-trimethylsilyloxynaphthalene-2-carboxylate
• CAS: 372980-41-1
• 化学式: C₁₇H₂₄O₃Si₂
• 分子量: 332.547
• InChiKey: SGSKFENRYUZSIQ-UHFFFAOYSA-N

物化性质

• 沸点：
  355.1±34.0 °C(Predicted)
• 密度：
  1.029±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.05
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  二氯亚磷酸甲酯 、 2-trimethylsiloxycarbonyl-3-trimethylsiloxynaphthalene 反应 0.5h， 生成 2-methoxynaphtho[2,3-d]-1,3,2-dioxaphosphorin-4-one
  参考文献：
  名称：

  1,3,2(1,4,2)-Dioxaphosphepins annelated with naphthalene fragment: Synthesis and steric structure

  摘要：

  Reaction of hexafluoroacetone and chloral with 2-R-naphtho-1,3,2-dioxaphosphorin-4-ones yields 2-R-2,5-dioxo-4,4-bis(trifluoromethyl)naphtho-1,3,2- and 2-R-2,5-dioxo-3-trichloromethylnaphtho-1,4,lambda(5)-dioxaphosphepins. Hydrolysis of the fluorophosphepins gives naphthyl -substituted fluorinated hydroxy ketones. The steric structure of the dioxaphosphepins and some fluorinated ketones was confirmed by single crystal X-ray diffraction. A competition between the pi-pi and halogen-halogen interactions and hydrogen bonds of classic type in the formation of crystal packing and supramolecular structure was revealed.

  DOI：

  10.1134/s107036320704007x
• 作为产物：
  描述：

  六甲基二硅氮烷 、 2-羟基-3-萘甲酸 在 碘 作用下， 以 neat (no solvent) 为溶剂， 反应 23.0h， 以63%的产率得到2-trimethylsiloxycarbonyl-3-trimethylsiloxynaphthalene
  参考文献：
  名称：

  无溶剂条件下HMDS合成羧酸三甲基甲硅烷基酯

  摘要：

  在几乎完全无溶剂的过程中，使用HMDS将多种结构不同的羧酸转化为三甲基甲硅烷基酯，而在某些情况下则需要催化量的碘。与已知方法相比，该方法具有多个优点：未处理的反应物，空气气氛，温和和中性条件，不产生卤化氢，不需要额外的碱，废物量少，完全无需色谱法，能源消耗低以及可操作简单。

  DOI：

  10.1016/j.tet.2016.08.003

文献信息

• Reaction of 2-R-naphtho[2,3-d][1,3,2]dioxaphosphinin-4-ones with arylidene derivatives of malonic acid esters: synthesis, molecular and crystal structures of 5-oxo-2-R-naphtho[2,3-f][1,2]oxaphosphepine 2-oxides
  作者：V. F. Mironov、G. A. Ivkova、M. N. Dimukhametov、Sh. K. Latypov、I. A. Litvinov

  DOI：10.1007/s11172-023-3865-2

  日期：2023.4

  3,2]dioxaphosphinin-4-ones with derivatives of β-dicarbonyl compounds, such as bis(2,2,3,3-tetrafluoropropyl) benzylidene- and 4-bromobenzylidenemalonates, afforded seven-membered heterocycles, 5-oxo-2-R-naphtho[2,3-f][1,2]oxaphosphepine 2-oxides, with high regioselectivity and stereoselectivity. In all cases, the major diastereomers were isolated and their structures were established by quantum chemical

  2-R-萘并[2,3- d ][1,3,2]dioxaphosphiin-4-ones与双(2,2,3,3-四氟丙基)亚苄基等β-二羰基化合物衍生物的反应- 和 4-溴亚苄基丙二酸酯，提供七元杂环，5-oxo-2-R-naphtho[2,3- f][1,2]oxaphosphepine 2-oxides，具有高区域选择性和立体选择性。在所有情况下，主要的非对映异构体都是分离的，它们的结构是通过量子化学计算、核磁共振光谱和 X 射线衍射分析确定的。在晶体结构中，分子的七元杂环采用扭曲的船形构象。在溶液中，分子可以采用扭曲的船形构象和具有相似能量的椅子形构象。该过程还涉及螺环正膦的可逆动力学控制形成，螺环正逐渐转化为热力学更稳定的 1,2-oxaphosphepines。该反应在温和条件下进行，并导致 P-C 和 C-C 键以及磷酰基的形成。
• Synthesis of trimethylsilyl carboxylates by HMDS under solvent-free conditions
  作者：Marjan Jereb、Janja Lakner

  DOI：10.1016/j.tet.2016.08.003

  日期：2016.9

  carboxylic acids were transformed into their trimethylsilyl esters with HMDS in a practically completely solvent-free process, while a catalytic amount of iodine was required in some cases. The process has several advantages over the known methods: untreated reactants, air atmosphere, mild and neutral conditions, no evolution of hydrogen halide, no need of an additional base, low amount of waste, completely

  在几乎完全无溶剂的过程中，使用HMDS将多种结构不同的羧酸转化为三甲基甲硅烷基酯，而在某些情况下则需要催化量的碘。与已知方法相比，该方法具有多个优点：未处理的反应物，空气气氛，温和和中性条件，不产生卤化氢，不需要额外的碱，废物量少，完全无需色谱法，能源消耗低以及可操作简单。
• 1,3,2(1,4,2)-Dioxaphosphepins annelated with naphthalene fragment: Synthesis and steric structure
  作者：L. M. Burnaeva、V. F. Mironov、L. M. Abdrakhmanova、A. T. Gubaidullin、R. Z. Musin、G. A. Ivkova、I. A. Litvinov、Sh. K. Latypov、A. A. Balandina、I. V. Konovalova

  DOI：10.1134/s107036320704007x

  日期：2007.4

  Reaction of hexafluoroacetone and chloral with 2-R-naphtho-1,3,2-dioxaphosphorin-4-ones yields 2-R-2,5-dioxo-4,4-bis(trifluoromethyl)naphtho-1,3,2- and 2-R-2,5-dioxo-3-trichloromethylnaphtho-1,4,lambda(5)-dioxaphosphepins. Hydrolysis of the fluorophosphepins gives naphthyl -substituted fluorinated hydroxy ketones. The steric structure of the dioxaphosphepins and some fluorinated ketones was confirmed by single crystal X-ray diffraction. A competition between the pi-pi and halogen-halogen interactions and hydrogen bonds of classic type in the formation of crystal packing and supramolecular structure was revealed.