2,2-dimethyl-5(S)-<methyl>-1,3-dioxolane-4(R)-carboxylic acid | 147727-16-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 2,2-dimethyl-5(S)-<methyl>-1,3-dioxolane-4(R)-carboxylic acid
• 英文别名: 2,2-dimethyl-5(S)-{[N-(3-cyanoindolyl)]methyl}-1,3-dioxolane-4(R)-carboxylic acid；(4R,5S)-5-[(3-cyanoindol-1-yl)methyl]-2,2-dimethyl-1,3-dioxolane-4-carboxylic acid
• CAS: 147727-16-0
• 化学式: C₁₆H₁₆N₂O₄
• 分子量: 300.314
• InChiKey: GDOCGNJOHPBUBF-UONOGXRCSA-N

物化性质

• 沸点：
  530.3±50.0 °C(predicted)
• 密度：
  1.34±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  84.5
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2,2-dimethyl-5(S)-<methyl>-1,3-dioxolane-4(R)-carboxylic acid 在 N-甲基吗啉 、 吡啶 、 氯甲酸异丁酯 作用下， 以 四氢呋喃 为溶剂， 反应 0.55h， 生成 1-[(4S,5R)-2,2-Dimethyl-5-(pyridin-2-ylsulfanyl)-[1,3]dioxolan-4-ylmethyl]-1H-indole-3-carbonitrile
  参考文献：
  名称：

  Intramolecular addition of a dioxolanyl radical to the indole nucleus: preparation of enantiomerically pure, oxygenated perhydro-3H-pyrrolo[1,2-a]indoles

  摘要：

  The cyclization of dioxolanyl radicals, which were generated by the Barton tartrate-derived thiohydroxamate ester (mixed anhydride) procedure, with an indole nucleus has been explored. The products derived from these reactions have been identified and their chemistry investigated with the goal of uncovering new entries into enantiomerically pure, mitomycin-like structures. Thus, the photolysis of 1-hydroxy-2-thiopyridone ester 8c and 1-hydroxy-4-methylthiazole-2(3H)-thione ester gd has been conducted with UV and visible light. The photochemistry of the products, namely, dimer 9, dihydroindole 12a, indole 11, and thiazole 13c, derived from the thiohydroxamate esters and putative intermediates 18a and 18b, was also explored.

  DOI：

  10.1021/jo00062a019
• 作为产物：
  描述：

  3-氰基吲哚 在 吡啶 、 lithium hydroxide 、 三氟甲磺酸酐 、 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 反应 4.58h， 生成 2,2-dimethyl-5(S)-<methyl>-1,3-dioxolane-4(R)-carboxylic acid
  参考文献：
  名称：

  Intramolecular addition of a dioxolanyl radical to the indole nucleus: preparation of enantiomerically pure, oxygenated perhydro-3H-pyrrolo[1,2-a]indoles

  摘要：

  The cyclization of dioxolanyl radicals, which were generated by the Barton tartrate-derived thiohydroxamate ester (mixed anhydride) procedure, with an indole nucleus has been explored. The products derived from these reactions have been identified and their chemistry investigated with the goal of uncovering new entries into enantiomerically pure, mitomycin-like structures. Thus, the photolysis of 1-hydroxy-2-thiopyridone ester 8c and 1-hydroxy-4-methylthiazole-2(3H)-thione ester gd has been conducted with UV and visible light. The photochemistry of the products, namely, dimer 9, dihydroindole 12a, indole 11, and thiazole 13c, derived from the thiohydroxamate esters and putative intermediates 18a and 18b, was also explored.

  DOI：

  10.1021/jo00062a019

文献信息

• Ziegler Frederick E., Harran Patrick G., J. Org. Chem., 58 (1993) N 10, S 2768-2773
  作者：Ziegler Frederick E., Harran Patrick G.

  DOI：——

  日期：——
• Intramolecular addition of a dioxolanyl radical to the indole nucleus: preparation of enantiomerically pure, oxygenated perhydro-3H-pyrrolo[1,2-a]indoles
  作者：Frederick E. Ziegler、Patrick G. Harran

  DOI：10.1021/jo00062a019

  日期：1993.5

  The cyclization of dioxolanyl radicals, which were generated by the Barton tartrate-derived thiohydroxamate ester (mixed anhydride) procedure, with an indole nucleus has been explored. The products derived from these reactions have been identified and their chemistry investigated with the goal of uncovering new entries into enantiomerically pure, mitomycin-like structures. Thus, the photolysis of 1-hydroxy-2-thiopyridone ester 8c and 1-hydroxy-4-methylthiazole-2(3H)-thione ester gd has been conducted with UV and visible light. The photochemistry of the products, namely, dimer 9, dihydroindole 12a, indole 11, and thiazole 13c, derived from the thiohydroxamate esters and putative intermediates 18a and 18b, was also explored.