<3-Nitro-4-acetoxy-phenyl>-trimethylammonium-iodid | 21259-22-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚酯
• 英文名称: <3-Nitro-4-acetoxy-phenyl>-trimethylammonium-iodid
• CAS: 21259-22-3
• 化学式: C₁₁H₁₅N₂O₄*I
• 分子量: 366.156
• InChiKey: XZCYWVWLODXZCN-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -1.28
• 重原子数：
  18.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  69.44
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  2-硝基-4-氨基苯酚 在 sodium acetate 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 生成 <3-Nitro-4-acetoxy-phenyl>-trimethylammonium-iodid
  参考文献：
  名称：

  Nucleophilic micelles. II. Effect on the rate of solvolysis of neutral, positively, and negatively charged esters of varied chain length when incorporated into nonfunctional and functional micelles of neutral, positive, and negative charge

  摘要：

  DOI：

  10.1021/ja01007a040

文献信息

• Water Soluble Steroids with Catalytic Substituents II. Synthesis of 3β-(4(5)-Imidazolyl)-5α-androstane-11β, 17β,-diamine and Comparison of its Catalytic Properties with Those of 17β-(4(5)-Imidazolyl)-5α-androstane-3β, 11β-diamine
  作者：J. Peter Guthrie、Yasutsugu Ueda

  DOI：10.1139/v73-586

  日期：1973.12.1

  3β-(4(5)-Imidazolyl)-5α-androstane-11β,17β-diamine, 15, has been synthesized in a multistep process from adrenosterone, 2, starting with lithium ammonia reduction to give 11α,17β-dihydroxy-5α-androstan-3-one, 3, which was converted to its diacetate, 4. Ethynylation at the 3 keto group gave the ethynyl triol 5, purified as its11,17-diacetate 6. Acid catalyzed rearrangement of 6 gave 3-acetyl-5α-androst-2-ene-11α,17β-diol diacetate, 7. This was hydrogenated, and then subjected to base catalyzed hydrolysis and equilibration to give crystalline 3β-acetyl-5α-androstane-11α,17β-diol, 9, which was converted to 3β-acetoxyacetyl-5α-androstane-11α,17β-diol, 10, using lead tetraacetate. After hydrolysis to the triol, 11, the Weidenhagen reaction led to formation of 3β-imidazolyl-5α-androstane-11α,17β-diol, 12. Finally oxidation to the dione, 13, formation of the dioxime, 14, and hydrogénation give 15. As expected 15 is a better catalyst than 17β-(4(5)-imidazolyl-5α-androstane-3β,11β-diamine, 1, for the hydrolysis of aryl esters of acids with hydrophobic substituents, but the effect is small. With 1 there is a marked electrostatic rate enhancement or retardation when charged groups are present on the aryl esters; this effect is much smaller for 15.

  3β-(4(5)-咪唑基)-5α-雄烷-11β,17β-二胺，15，是从腺酮，2，经过多步合成的，首先进行锂氨还原得到11α,17β-二羟基-5α-雄甾-3-酮，3，然后转化为其二乙酸酯，4。在3酮基上进行乙炔基化得到乙炔三醇5，纯化为其11,17-二乙酸酯6。酸催化6的重排得到3-乙酰基-5α-雄烷-2-烯-11α,17β-二醇二乙酸酯，7。这经过氢化，然后经过碱催化水解和平衡得到结晶的3β-乙酰基-5α-雄烷-11α,17β-二醇，9，它被转化为3β-乙酰氧乙酰-5α-雄烷-11α,17β-二醇，10，使用四乙酸铅。水解为三醇后，11，魏登哈根反应导致形成3β-咪唑基-5α-雄烷-11α,17β-二醇，12。最后氧化为二酮，13，形成二肟，14，和氢化得到15。如预期的那样，15比17β-(4(5)-咪唑基-5α-雄烷-3β,11β-二胺，1，更好地催化含疏水取代基的芳基酯的水解，但效果很小。对于1，当芳基酯上存在带电基团时，会出现明显的静电速率增强或减缓；而对于15，这种效应要小得多。