N-(ribityl),N'-(Boc)-diamino-4,5-dimethylbenzene | 569343-11-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-(ribityl),N'-(Boc)-diamino-4,5-dimethylbenzene
• 英文别名: tert-butyl N-[4,5-dimethyl-2-[[(2S,3S,4R)-2,3,4,5-tetrahydroxypentyl]amino]phenyl]carbamate
• CAS: 569343-11-9
• 化学式: C₁₈H₃₀N₂O₆
• 分子量: 370.446
• InChiKey: MHCYDQHOQXKWDW-XHSDSOJGSA-N

物化性质

• 沸点：
  585.6±50.0 °C(Predicted)
• 密度：
  1.287±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  26
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  131
• 氢给体数：
  6
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  N-(ribityl),N'-(Boc)-diamino-4,5-dimethylbenzene 在 盐酸 、 氧气 作用下， 以 水 为溶剂， 反应 99.0h， 生成 5,6-二甲基苯并咪唑
  参考文献：
  名称：

  Rational improvement of the synthesis of 1-deazariboflavin

  摘要：

  The cofactor forms of riboflavin (FMN and FAD) play a crucial role in the mediation of both enzymatic processes and light perception by photo-sensitive proteins, and thus structural analogues of this chromophore are highly useful tools to assist in the elucidation of enzymatic mechanisms. 1-Deazariboflavin has been rarely utilised for this purpose, due in part to its previously difficult and inefficient synthesis. Recent examination has enabled a remarkable improvement in the overall synthetic yield from 11.0 to 613%, allowing reliable production of 1-deazariboflavin for use as a tool in enzymatic mechanistic determination. (C) 2015 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2015.01.053
• 作为产物：
  描述：

  4，5-二甲基-1，2-苯二胺 在 sodium cyanoborohydride 、 sodium carbonate 作用下， 以 1,4-二氧六环 、 甲醇 、 水 为溶剂， 反应 53.0h， 生成 N-(ribityl),N'-(Boc)-diamino-4,5-dimethylbenzene
  参考文献：
  名称：

  通过用5-Deazaflavin类似物交换其黄素辅因子将脱卤酶转化为硝基还原酶

  摘要：

  天然和工程化的硝基还原酶很少支持将硝基芳族化合物完全还原成其胺产物，并且更典型地，转化仅限于羟胺中间体的形成。有效使用这些酶还需要NAD（P）H的再生系统，以避免与这种天然还原剂相关的成本。碘酪氨酸脱碘酶与许多硝基还原酶是同一结构超家族的成员，但不直接消耗NAD（P）H的还原当量，也不显示硝基还原酶活性。但是，将其黄素辅因子与5-deazaflavin类似物进行交换会极大地抑制其天然脱碘酶活性，并导致显着的硝基还原酶活性，从而在方便和廉价的NaBH 4存在下支持将其完全还原为胺产物。。

  DOI：

  10.1002/anie.201703628

文献信息

• Synthesis and Electrochemical Properties of Structurally Modified Flavin Compounds
  作者：Madina Mansurova、Melissa S. Koay、Wolfgang Gärtner

  DOI：10.1002/ejoc.200800504

  日期：2008.11

  Four structurally modified flavin compounds have been synthesized and characterized for their redox potential by chemical reduction with sodium dithionite. Besides the previously reported 1- and 5-deazariboflavin, a 7,8-didemethyl derivative and an 8-isopropylriboflavin have been obtained. The synthesis of these compounds started in all cases from appropriately substituted anilines that were condensed

  已经合成了四种结构改性的黄素化合物，并通过用连二亚硫酸钠化学还原来表征它们的氧化还原电位。除了先前报道的 1- 和 5- 脱氮杂核黄素外，还获得了 7,8- 二甲基衍生物和 8-异丙基核黄素。在所有情况下，这些化合物的合成都是从适当取代的苯胺开始，该苯胺与核糖基链缩合，然后完成退火的三环结构。双去甲基和异丙基化合物的吸收最大值与核黄素相似（分别为 436 和 448 nm），而 1-去氮杂核黄素显示出红移吸收（λmax = 537 nm），而 5-去氮杂核黄素则显示出红移吸收（λmax = 400 纳米）。四种修饰的黄素化合物的中点电位 (E0') 通过电位滴定法测定，使用核黄素作为参考化合物。两种烷基改性黄素的负中点电位略低，而与参考化合物相比，两种脱氮化合物具有更多的负中点值。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany
• Formation of the Dimethylbenzimidazole Ligand of Coenzyme B₁₂ under Physiological Conditions by a Facile Oxidative Cascade
  作者：Lori A. Maggio-Hall、Pieter C. Dorrestein、Jorge C. Escalante-Semerena、Tadhg P. Begley

  DOI：10.1021/ol034530m

  日期：2003.6.1

  Dimethylbezimidazole, the axial ligand of vitamin B-12, is synthesized from riboflavin by a two-electron oxidation, a retro-aldol condensation, and a second two-electron oxidation. This oxidative cascade readily takes place nonenzymatically under physiological conditions.
• Improved Chemical Syntheses of 1- and 5-Deazariboflavin
  作者：Erin E. Carlson、Laura L. Kiessling

  DOI：10.1021/jo049859f

  日期：2004.4.1

  The cofactor flavin adenine dinucleotide (FAD) is required for the catalytic activity of a large class of enzymes known as flavoenzymes. Because flavin cofactors participate in catalysis via a number of different mechanisms, isoalloxazine analogues are valuable for mechanistic studies. We report improved chemical syntheses for the preparation of the two key analogues, 5-deazariboflavin and 1-deazariboflavin.
• Rational improvement of the synthesis of 1-deazariboflavin
  作者：Andrew C. Wood、David W. Knight、Gerald Richter

  DOI：10.1016/j.tet.2015.01.053

  日期：2015.3

  The cofactor forms of riboflavin (FMN and FAD) play a crucial role in the mediation of both enzymatic processes and light perception by photo-sensitive proteins, and thus structural analogues of this chromophore are highly useful tools to assist in the elucidation of enzymatic mechanisms. 1-Deazariboflavin has been rarely utilised for this purpose, due in part to its previously difficult and inefficient synthesis. Recent examination has enabled a remarkable improvement in the overall synthetic yield from 11.0 to 613%, allowing reliable production of 1-deazariboflavin for use as a tool in enzymatic mechanistic determination. (C) 2015 Published by Elsevier Ltd.
• Conversion of a Dehalogenase into a Nitroreductase by Swapping its Flavin Cofactor with a 5-Deazaflavin Analogue
  作者：Qi Su、Petrina A. Boucher、Steven E. Rokita

  DOI：10.1002/anie.201703628

  日期：2017.8.28

  formation of the hydroxylamine intermediates. Efficient use of these enzymes also requires a regenerating system for NAD(P)H to avoid the costs associated with this natural reductant. Iodotyrosine deiodinase is a member of the same structural superfamily as many nitroreductases but does not directly consume reducing equivalents from NAD(P)H, nor demonstrate nitroreductase activity. However, exchange

  天然和工程化的硝基还原酶很少支持将硝基芳族化合物完全还原成其胺产物，并且更典型地，转化仅限于羟胺中间体的形成。有效使用这些酶还需要NAD（P）H的再生系统，以避免与这种天然还原剂相关的成本。碘酪氨酸脱碘酶与许多硝基还原酶是同一结构超家族的成员，但不直接消耗NAD（P）H的还原当量，也不显示硝基还原酶活性。但是，将其黄素辅因子与5-deazaflavin类似物进行交换会极大地抑制其天然脱碘酶活性，并导致显着的硝基还原酶活性，从而在方便和廉价的NaBH 4存在下支持将其完全还原为胺产物。。