3,5-bis(dimethylamino)benzyl alcohol | 198623-58-4

• 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: 3,5-bis(dimethylamino)benzyl alcohol
• 英文别名: 3,5-(N,N,N',N'-tetramethyl)diamino benzyl alcohol；[3,5-Bis(dimethylamino)phenyl]methanol
• CAS: 198623-58-4
• 化学式: C₁₁H₁₈N₂O
• 分子量: 194.277
• InChiKey: LWIBTERMIIHDPH-UHFFFAOYSA-N

物化性质

• 沸点：
  351.9±42.0 °C(Predicted)
• 密度：
  1.083±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  26.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3,5-bis(dimethylamino)benzyl alcohol 在 氢溴酸 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 生成 O²-(3,5-bis(dimethylamino)benzyl)-1-(N,N-diethylamino)-diazen-1-ium-1,2-diolate
  参考文献：
  名称：

  O2-苄基取代的二氮烯二醇盐中一氧化氮的受控光化学释放

  摘要：

  已经启动了对二氮烯二醇 (R2N-N(O)=NO-) 潜在光敏保护基团的研究，这里研究了间位给电子基团对 O2-苄基取代的二氮烯二醇 (R2N-N(O) )=NOCH2Ar) 被报道。母体苄基衍生物 (Ar = Ph) 的光解几乎完全导致不希望的光化学反应 - 亚硝胺和氧氮烯中间体的形成，如果有的话，二氮烯二醇的光释放很少。我们已经能够使用元取代来调整这些苄基系统的光化学。已显示所需的二氮烯二醇光离型剂随着更强的 pi 供体间位取代基变得更加坚固。这种效应已经通过用 1H NMR 光谱直接观察光释放的二氮烯二醇和在高和低 pH 溶液中进行的 NO 定量测量得到证实。此外，观察到的 NO 释放速率与二氮烯二醇在水溶液中正常热分解的预期速率一致，并且也显示出相同的 pH 依赖性。

  DOI：

  10.1021/ja026900s
• 作为产物：
  描述：

  methyl 3,5-N,N,N',N'-tetramethylaminobenzoate 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 以94%的产率得到3,5-bis(dimethylamino)benzyl alcohol
  参考文献：
  名称：

  Discovery and structure-activity studies of a novel series of pyrido[2,3-d]pyrimidine tyrosine kinase inhibitors

  摘要：

  The inhibition of tyrosine kinase-mediated signal transduction pathways represents a therapeutic approach to the intervention of proliferative diseases such as cancer, atherosclerosis, and restenosis. A novel series of pyrido[2,3-d]pyrimidine inhibitors of the PDGFr, bFGFr, and c-Src tyrosine kinases was developed from compound library screening and lead optimization.(1) In addition, highly selective inhibitors of the FGFr tyrosine kinase were also discovered and developed from this novel series of pyrido[2,3-d]pyrimidines. The syntheses, biological evaluation, and structure-activity relationships of this series are reported. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(97)00445-9

文献信息

• Monomer-on-Monomer (MoM) Mitsunobu Reaction: Facile Purification Utilizing Surface-Initiated Sequestration
  作者：Pradip K. Maity、Alan Rolfe、Thiwanka B. Samarakoon、Saqib Faisal、Ryan D. Kurtz、Toby R. Long、Alexander Schätz、Daniel L. Flynn、Robert N. Grass、Wendelin J. Stark、Oliver Reiser、Paul R. Hanson

  DOI：10.1021/ol1022382

  日期：2011.1.7

  A monomer-on-monomer (MoM) Mitsunobu reaction utilizing norbornenyl-tagged (Nb-tagged) reagents is reported, whereby purification was rapidly achieved by employing ring-opening metathesis polymerization, which was initiated by any of three methods utilizing Grubbs catalyst: (i) free catalyst in solution, (ii) surface-initiated catalyst-armed silica, or (iii) surface-initiated catalyst-armed Co/C magnetic nanoparticles.
• Photochemical Heterolysis of 3,5-Bis(dimethylamino)benzyl Alcohols and Esters: Generation of a Benzyl Cation with a Low-Energy Triplet State
  作者：Raffaele R. Perrotta、Arthur H. Winter、Daniel E. Falvey

  DOI：10.1021/ol102606m

  日期：2011.1.21

  An earlier computational study (CASPT2/pVDZ) by Winter et al. predicts the 3,5-bis(dimethylamino)benzyl cation to have nearly degenerate singlet and triplet states. Through product studies it is demonstrated that photolysis of 3,5-bis(dimethylamino)benzyl alcohol and its corresponding acetate and phenylacetate esters in alcoholic solvents produces a solvent incorporated adduct, 3,5-bis(dimethylamino)benzyl ethers, and 3,5-bis(dimethylamino)toluene.