o-bis-((3-hydroxypropyl)methylamino)benzene | 78269-34-8

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: o-bis-((3-hydroxypropyl)methylamino)benzene
• 英文别名: o-bis-[(3-hydroxypropyl)methylamino]benzene；3-[2-[3-hydroxypropyl(methyl)amino]-N-methylanilino]propan-1-ol
• CAS: 78269-34-8
• 化学式: C₁₄H₂₄N₂O₂
• 分子量: 252.357
• InChiKey: NAAXTMRTTWWTOA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.32
• 重原子数：
  18.0
• 可旋转键数：
  8.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  46.94
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  o-bis-((3-hydroxypropyl)methylamino)benzene 在 4-二甲氨基吡啶 、 氯化亚砜 作用下， 以 二氯甲烷 为溶剂， 以52 %的产率得到1,11-dimethyl-1,2,3,4,8,9,10,11-octahydrobenzo[h][1,3]dioxa[2]thia[7,10]diazacyclotridecine 6-oxide
  参考文献：
  名称：

  通过环化/扩环级联反应合成大环和中型环的模块化策略

  摘要：

  大环和中型环在许多科学领域和技术中都很重要，但使用现有方法很难制造，尤其是大规模制造。本文概述了一种策略，通过该策略可以使用环化/扩环（CRE）级联反应来制备官能化大环和中等大小的环，而不需要采用高稀释条件。 CRE 级联反应专门通过动力学有利的 5-7 元环环化步骤进行操作；这意味着避免了通常与经典的端到端大环化反应相关的问题。已经开发出一种模块化合成方法，以促进所需线性前体的简单组装，然后可以使用九种 CRE 方案之一将其转化为极其广泛的官能化大环化合物和中等大小的环。

  DOI：

  10.1021/jacs.4c00659
• 作为产物：
  描述：

  3-氯-1-丙醇 、 1-N,2-N-二甲基苯-1,2-二胺 在 calcium carbonate 作用下， 以 水 为溶剂， 生成 o-bis-((3-hydroxypropyl)methylamino)benzene
  参考文献：
  名称：

  Synthesis, Cyclic Voltammetry, and Photophysical Properties of a Bridged o-Phenylenediamine−C₆₀ Dyad

  摘要：

  The synthesis, complete spectroscopic characterization, cyclic voltammetry, and photophysical measurements of a new omicron-phenylenediamine C-60 dyad are described. By using a tether strategy, only a single regioisomer was obtained. Cyclic voltammetry measurements indicate that the two electroactive groups do not interact in their singlet ground states. Photophysical investigations reveal a rapid photoinduced electron transfer between the singlet excited state of the fullerene acceptor and the omicron-phenylenediamine donor, yielding a charge-separated radical pair.

  DOI：

  10.1021/ol005992s

文献信息

• Macrocyclic Cyclo[n]malonates – Synthetic Aspects and Observation of Columnar Arrangements by X-ray Crystallography
  作者：Nikos Chronakis、Torsten Brandmüller、Christian Kovacs、Uwe Reuther、Wolfgang Donaubauer、Frank Hampel、Felix Fischer、François Diederich、Andreas Hirsch

  DOI：10.1002/ejoc.200500921

  日期：2006.5

  interest are the macrocyclic bismalonates, as they show pronounced crystallisability and arrange into columnar motifs in the solid state. They feature distinctive dihedral angles: all ester moieties adopt anti conformations whereas the planes of the carboxy moieties of each malonate residue arrange in an approximately orthogonal fashion. The latter geometry is enforced by the macrocyclic structures, as

  通过丙二酰二氯与α,ω-二醇缩合，一步法合成了多种非手性和手性大环低聚丙二酸酯。我们通过改变二醇中间隔物的长度和类型研究了这种方法的适用性。产品分布分析表明，单体、二聚或三聚大环丙二酸酯的优先形成可以通过选择具有连接羟基的特定间隔基的二醇来控制。特别令人感兴趣的是大环双丙二酸酯，因为它们显示出明显的结晶性并在固态下排列成柱状图案。它们具有独特的二面角：所有酯部分都采用反构象，而每个丙二酸酯残基的羧基部分的平面以近似正交的方式排列。正如剑桥结构数据库中的构象搜索所揭示的那样，后一种几何结构由大环结构强制执行。X 射线衍射数据表明，C=O...H-C 和 C-O...H-C 氢键稳定了二聚环的柱状排列并形成管状组件。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)
• Tetradentate 14-membered tert-phosphino-containing macrocycles
  作者：Evan P. Kyba、Raymond E. Davis、Carl W. Hudson、A. Meredith John、S. Bruce Brown、Michael J. McPhaul、Ling-Kang Liu、Ann C. Glover

  DOI：10.1021/ja00403a041

  日期：1981.7
• Th-Symmetrical Hexakisadducts of C60 with a Densely Packed π-Donor Shell Can Act as Energy- or Electron-Transducing Systems
  作者：Michael Diekers、Chuping Luo、Dirk M. Guldi、Andreas Hirsch

  DOI：10.1002/1521-3765(20020215)8:4<979::aid-chem979>3.0.co;2-6

  日期：2002.2.15

  For the first time several T-h-symmetrical hexakisadducts of C-60 bearing up to six electro and photoactive o-phenylene diamine or 9,10-dialkoxyanthracene moieties were synthesized and subjected to photoinduced electron/energy-transfer studies. Both donors form a densely packed pi-donor shell surrounding the fullerene core. In these novel core -shell ensembles (7 and 19), either an efficient energy transfer from the dialkoxyanthracene periphery, or an electron transfer from the o-phenylene diamine periphery transduces the flow of excited-state energy or electrons, respectively, to the fullerene moiety, which resides in the central core. Due to the relatively high reduction potential of the fullerene core, which is anodically shifted by approximate to 0.7 V, compared with that of pristine C-60, the outcome of these intra- molecular reactions depends mainly on the donor ability of the peripheral system. Interestingly, the charge-separated state in the o-phenylene diamine heptad (7; tau = 2380 ns in benzonitrile) is stabilized by a factor of 20 relative to the corresponding o-phenylene diamine dy-ad (6; tau = 120 ns in benzonitrile), an effect that points unequivocally to the optimized storage of charges in this highly functionalized fullerene ensemble.
• KYBA E. P.; DAVIS R. E.; HUDSON C. W.; JOHN A. M.; BROWN S. B.; MCPHAUL M+, J. AMER. CHEM. SOC., 1981, 103, NO 13, 3868-3875
  作者：KYBA E. P.、 DAVIS R. E.、 HUDSON C. W.、 JOHN A. M.、 BROWN S. B.、 MCPHAUL M+

  DOI：——

  日期：——