bis(1,8-bis(dimethylamino)naphthalen-2-yl)(phenyl)methanol | 1233939-17-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: bis(1,8-bis(dimethylamino)naphthalen-2-yl)(phenyl)methanol
• 英文别名: bis[1,8-bis(dimethylamino)naphth-2-yl]phenylmethanol；Bis[1,8-bis(dimethylamino)naphthalen-2-yl]-phenylmethanol
• CAS: 1233939-17-7
• 化学式: C₃₅H₄₀N₄O
• 分子量: 532.729
• InChiKey: HIXXIGFTCIKEMI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  40
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  33.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-benzoyl-1,8-bis(dimethylamino)naphthalene 、 2-lithio-1,8-bis(dimethylamino)naphthalene 以 乙醚 为溶剂， 以50%的产率得到bis(1,8-bis(dimethylamino)naphthalen-2-yl)(phenyl)methanol
  参考文献：
  名称：

  2-三氟乙酰基-1,8-双（二​​甲基氨基）萘与强有机碱的反应：1-NMe 2基团的质子化导致苯并[g]吲哚衍生物的形成与向C O基团的亲核加成

  摘要：

  通过用2-锂-1,8-双（二​​甲基氨基）萘处理产生相应的苯并[ g ]吲哚的新方法来封闭2-三氟乙酰基和2-乙氧基羰基-1,8-双（二​​甲基氨基）萘中的吡咯环用不同的烷基锂和芳基锂化合物以及LDA检查了它们的衍生物。发现当芳基锂试剂在碳负离子中心的邻位含有NMe 2基团时，使用芳基锂试剂可获得最高产率的苯并[ g ]吲哚（高达70％）。在所有其他情况下，由于碳通常通过分子间加成而形成无环醇。O组非常占优势。在2-锂-N，N-二甲基苯胺的情况下，通过反应过渡态的特定结构说明了底物中N-Me基团去质子化的显着促进，然后是吡咯环化。

  DOI：

  10.1016/j.tet.2017.05.013

文献信息

• 1,8,1′,8′-Tetrakis(dimethylamino)-2,2′-dinaphthylmethanols: Double <i>In/Out</i> Proton Sponges with Low-Barrier Hydrogen-Bond Switching
  作者：Alexander F. Pozharskii、Alexander V. Degtyarev、Valery A. Ozeryanskii、Oksana V. Ryabtsova、Zoya A. Starikova、Gennadii S. Borodkin

  DOI：10.1021/jo100384s

  日期：2010.7.16

  Previously unknown bis[1,8-bis(dimethylamino)naphth-2-yl]phenylmethanol (5) and bis[1,8-bis(dimethylamino)naphth-2-yl]methanol (6) have been obtained and studied by combination of X-ray, NMR, and IR techniques at variable temperature. It has been established that both proton sponge units in the solid tertiary alcohol 5 exist in nonconventional in/out form, one of which is fixed by intramolecular O-H center dot center dot center dot N hydrogen bonding. In solution, a fast interconversion of two isoenergetic hydrogen chelates occurs which can be frozen below 183 K. Unlike this, the secondary alcohol 6 in the solid at 100 K adopts the in/out-in/in conformation and at 293 K demonstrates a kind of dynamic behavior which can be described as temperature-driven dimer-induced rechelation. In solution under ambient conditions 6 exists as an equilibrating mixture of chelated and unchelated monomeric forms in a similar to 1:1.8 molar ratio.
• Reaction of 2-trifluoroacetyl-1,8-Bis(dimethylamino)naphthalene with strong organic bases: Deprotonation of 1-NMe2 group resulting in the formation of Benzo[g]indole derivatives versus nucleophilic addition to C O group
  作者：Alexander S. Antonov、Svetlana G. Kachalkina、Alexander F. Pozharskii、Gennady S. Borodkin、Aleksander Filarowski

  DOI：10.1016/j.tet.2017.05.013

  日期：2017.6

  8-bis(dimethylamino)naphthalenes via treatment with 2-lithium-1,8-bis(dimethylamino)naphthalene producing the corresponding benzo[g]indole derivatives, was examined with different alkyl- and aryllithium compounds as well as with LDA. It was found that the highest yields of benzo[g]indoles (up to 70%) are obtained with aryllithium reagents when they contain NMe2 group in ortho-position to the carbanionic centre

  通过用2-锂-1,8-双（二​​甲基氨基）萘处理产生相应的苯并[ g ]吲哚的新方法来封闭2-三氟乙酰基和2-乙氧基羰基-1,8-双（二​​甲基氨基）萘中的吡咯环用不同的烷基锂和芳基锂化合物以及LDA检查了它们的衍生物。发现当芳基锂试剂在碳负离子中心的邻位含有NMe 2基团时，使用芳基锂试剂可获得最高产率的苯并[ g ]吲哚（高达70％）。在所有其他情况下，由于碳通常通过分子间加成而形成无环醇。O组非常占优势。在2-锂-N，N-二甲基苯胺的情况下，通过反应过渡态的特定结构说明了底物中N-Me基团去质子化的显着促进，然后是吡咯环化。