N-4-methoxytritylglycine methyl ester | 261622-09-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: N-4-methoxytritylglycine methyl ester
• 英文别名: Methyl 2-[[(4-methoxyphenyl)-diphenylmethyl]amino]acetate
• CAS: 261622-09-7
• 化学式: C₂₃H₂₃NO₃
• 分子量: 361.441
• InChiKey: GGODRYRKDAXDLH-UHFFFAOYSA-N

物化性质

• 沸点：
  481.7±45.0 °C(Predicted)
• 密度：
  1.134±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  47.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-4-methoxytritylglycine methyl ester 在 正丁基锂 、 二异丁基氢化铝 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 0.5h， 生成 (E)-5-{[(4-Methoxy-phenyl)-diphenyl-methyl]-amino}-pent-3-en-1-ol
  参考文献：
  名称：

  Epoxidation of Peptidyl Olefin Isosteres. Stereochemical Induction Effect of Chiral Centers at Four Adjacent Cα Positions

  摘要：

  Four tripeptidyl olefin isosteres were prepared, each of which contains a single chiral center derived from the bulky amino acid phenylalanine at positions corresponding to the P-2-P'(2) positions of a protease substrate. The effect of these chiral centers on the stereochemical outcome of mCPBA epoxidation of the olefin functionality was studied. A chiral center at P-2 or P'(2) position has no significant effect, and the P'(1) position exerts a small stereoselectivity. A chiral center at the P-1 position, on the other hand, has a profound chiral induction effect on the epoxidation reaction. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00036-3
• 作为产物：
  描述：

  甘氨酸甲酯盐酸盐 、 4-甲氧基三苯基氯甲烷 在 三乙胺 作用下， 以 氯仿 为溶剂， 反应 6.0h， 以80%的产率得到N-4-methoxytritylglycine methyl ester
  参考文献：
  名称：

  Canle, Moises L.; Clegg, William; Demirtas, Ibrahim, Journal of the Chemical Society. Perkin Transactions 2 (2001), 2000, # 1, p. 85 - 92

  摘要：

  DOI：

文献信息

• Substituent effects upon rates of deamination and base strengths of substituted N-tritylamines
  作者：Moisés Canle L.、Ibrahim Demirtas、Howard Maskill

  DOI：10.1039/b104916j

  日期：——

  Substituted N-tritylamines undergo deamination in aqueous acidic solution containing organic cosolvents, and follow a pseudo first-order specific acid-catalysis rate law (kobs = k0 + kH[H3O+]); the products are the corresponding trityl alcohols in equilibrium with the trityl carbenium ions, and ammonium ions. The change from 4,4′-dimethoxy- to 4,4′,4″-trimethoxy-tritylamine increases reactivity by a factor of about 30 in both k0 and kH, but N-alkyl and N-aryl groups have much greater effects (ca. 106 for both k0 and kH for 4,4′-dimethoxytritylamine) which are largely independent of the nature of the N-alkyl and N-aryl groups. The anions of the catalytic strong acids (perchlorate, chloride, bromide, and nitrate) have only small effects as also does the concentration of acetonitrile as cosolvent; ethanoic acid as cosolvent is mildly rate-enhancing. Substituents in the aniline residue of N-(4,4′-dimethoxytrityl)anilines have virtually no effect upon either k0 or kH (ρ = 0 for both). The results are interpreted by a mechanism involving a pre-equilibrium heterolysis of the (substituted) tritylammonium ion to give an ion–molecule pair which may undergo diffusional or acid-catalysed dissociation before the (substituted) trityl cation undergoes equilibrium nucleophilic capture by water. Base strengths of some substituted N-tritylamines have been measured; the substituted N-trityl group causes all amines (aliphatic and aromatic) to be comparably strongly basic (pKBH+ca. 9).

  替代的N-三苯基胺在含有有机共溶剂的酸性水溶液中发生脱氨反应，并遵循伪一级的特定酸催化速率定律（kobs = k0 + kH[H3O+]); 产生的产物是相应的三苯基醇，与三苯基阳离子和铵离子处于平衡状态。从4,4′-二甲氧基到4,4′,4″-三甲氧基三苯基胺的变化使反应性增加了大约30倍，在k0和kH中都是如此，但N-烷基和N-芳基取代基对反应性的影响更大（对于4,4′-二甲氧基三苯基胺，k0和kH的影响约为106），且这些影响在很大程度上独立于N-烷基和N-芳基取代基的性质。催化强酸的阴离子（高氯酸盐、氯离子、溴离子和硝酸盐）对反应的影响很小，乙腈作为共溶剂的浓度也没有显著影响；乙酸作为共溶剂略微增强了反应速率。在N-(4,4′-二甲氧基三苯基)苯胺的苯胺残基上的取代基对k0或kH几乎没有影响（ρ = 0）。这些结果通过一种机制进行了解释，该机制涉及（替代的）三苯基铵离子的前平衡异裂，形成一个离子-分子对，该对可能在（替代的）三苯基阳离子通过水进行平衡亲核捕获之前，发生扩散性或酸催化解离。一些替代的N-三苯基胺的碱性已被测量；替代的N-三苯基基团使所有胺（包括脂肪族和芳香族）具有相似的强碱性（pKBH+约为9）。
• Epoxidation of Peptidyl Olefin Isosteres. Stereochemical Induction Effect of Chiral Centers at Four Adjacent Cα Positions
  作者：Nurit Perlman、Mordechai Livneh、Amnon Albeck

  DOI：10.1016/s0040-4020(00)00036-3

  日期：2000.3

  Four tripeptidyl olefin isosteres were prepared, each of which contains a single chiral center derived from the bulky amino acid phenylalanine at positions corresponding to the P-2-P'(2) positions of a protease substrate. The effect of these chiral centers on the stereochemical outcome of mCPBA epoxidation of the olefin functionality was studied. A chiral center at P-2 or P'(2) position has no significant effect, and the P'(1) position exerts a small stereoselectivity. A chiral center at the P-1 position, on the other hand, has a profound chiral induction effect on the epoxidation reaction. (C) 2000 Elsevier Science Ltd. All rights reserved.
• Canle, Moises L.; Clegg, William; Demirtas, Ibrahim, Journal of the Chemical Society. Perkin Transactions 2 (2001), 2000, # 1, p. 85 - 92
  作者：Canle, Moises L.、Clegg, William、Demirtas, Ibrahim、Elsegood, Mark R.J.、Maskill, Howard

  DOI：——

  日期：——