2,2-dimethyl-1-(2-quinolinyl)-1-propanol | 202134-87-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 2,2-dimethyl-1-(2-quinolinyl)-1-propanol
• 英文别名: I+/--(1,1-Dimethylethyl)-2-quinolinemethanol；2,2-dimethyl-1-quinolin-2-ylpropan-1-ol
• CAS: 202134-87-0
• 化学式: C₁₄H₁₇NO
• 分子量: 215.295
• InChiKey: OXLLYFMIGBXCAO-UHFFFAOYSA-N

物化性质

• 熔点：
  70-72 °C
• 沸点：
  338.4±17.0 °C(Predicted)
• 密度：
  1.090±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  33.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-氯喹啉 、 特戊醛 在 萘 、 lithium 作用下， 以 四氢呋喃 为溶剂， 以29%的产率得到2,2-dimethyl-1-(2-quinolinyl)-1-propanol
  参考文献：
  名称：

  萘催化氯化硝化芳香杂环的锂化反应及与亲电试剂的反应

  摘要：

  萘催化各种chloroazines的还原性锂化（1，7，10，13以不同的亲电子的产率的情况下），在水解后，预期的官能化杂环与一个（2，8），两个（11，14A - d）和三个氮环（14e，f）中的原子。这种方法使我们能够在烷氧基钛存在下，通过与格氏试剂反应，将2-吡啶基锂与苄腈反应衍生的亚胺锂原位捕获。2,4-二甲氧基嘧啶（14a，c，d）在酸性条件下脱甲基，得到相应的尿嘧啶衍生物16。

  DOI：

  10.1016/s0040-4020(00)00318-5

文献信息

• Preparation of Nitrogen-Containing π-Deficient Heteroaromatic Grignard Reagents:  Oxidative Magnesiation of Nitrogen-Containing π-Deficient Halogenoheteroaromatics Using Active Magnesium
  作者：Osamu Sugimoto、Shigeru Yamada、Ken-ichi Tanji

  DOI：10.1021/jo026492a

  日期：2003.3.1

  The oxidative magnesiation of nitrogen-containing pi-deficient halogenoheteroaromatics using active magnesium was accomplished. Both magnesiation followed by addition of a carbonyl compound (Grignard reaction) and magnesiation in the presence of a carbonyl compound (Barbier reaction) were carried out to afford the corresponding product. Especially, the latter method enabled fused halogenodiazines such

  使用活性镁完成了含氮pi不足的卤代杂环芳烃的氧化放大作用。进行镁的放大，然后添加羰基化合物（格氏反应），以及在羰基的化合物存在下进行镁的放大（Barbier反应），得到相应的产物。特别地，后一种方法使稠合的卤素二嗪例如4-氯-1-苯基-1H-吡唑并[3，4-d]嘧啶或2-氯喹喔啉在温和的温度（-20至30℃）下氧化镁。
• Aggregative activation in heterocyclic chemistry. Part 5.† Lithiation of pyridine and quinoline with the complex base BuLi·Me2N(CH2)2OLi (BuLi·LiDMAE)
  作者：Philippe Gros、Yves Fort、Paul Caubère

  DOI：10.1039/a705027e

  日期：——

  It is shown that the complex base BuLi·LiDMAE reacts with pyridine to give metallated species which, after trapping by electrophiles, lead to 2-substituted pyridines in good to excellent yields. The same reactions have been less successfully performed with quinoline.

  研究表明，复杂的碱 BuLi·LiDMAE 与吡啶反应生成金属化物种，经过电亲体捕捉后，能够以良好至优异的收率生成 2-取代吡啶。同样的反应在喹啉上进行得不太成功。
• Preparation and Reaction of Quinolinyl (or Pyridinyl)phosphonium Salts with Base and Pivalaldehyde
  作者：Osamu Sugimoto、Minami Shimada、Akihiro Sato、Ken-ichi Tanji

  DOI：10.3987/com-11-12154

  日期：——

  alpha- and gamma-Heteroaryltriphenylphosphonium iodides were prepared by reaction of the corresponding heteroaryl iodides with triphenylphosphine. Reaction of beta-heteroaryl iodides with triphenylphosphine in the presence of a palladium catalyst gave beta-heteroaryltriphenylphosphonium iodides. Elimination of the heteroaryl group was achieved by treating the heteroaryltriphenylphosphonium iodides with a base. Further, the heteroaryl group was trapped with pivalaldehyde to introduce a pivaloyl substituent onto the heteroaromatic ring.
• Dehalogenation and Barbier-Type Hydroxyalkylation of π-Deficient Haloheterocycles Using Indium
  作者：Osamu Sugimoto、Ken-ichi Tanji、Eri Fukuda、Yukiko Takahashi、Natsumi Hirasawa

  DOI：10.3987/com-08-s(f)95

  日期：——

  The reaction of pi-deficient haloheterocycles with indium metal in water gave corresponding dehalogenated heterocycles. The use of diluted hydrochloric acid instead of water accelerated the reductive reactivity of indium metal. Furthermore, Barbier-type additions proceeded by reactions of alpha-iodoheterocycles with indium in the presence of pivalaldehyde.
• The tellurium–lithium exchange reaction: selective functionalization of electron-deficient heteroaromatics
  作者：Osamu Sugimoto、Muneyoshi Sudo、Ken-ichi Tanji

  DOI：10.1016/s0040-4020(01)00089-8

  日期：2001.3

  Electron-deficient heteroaromatic tellurides, which was obtained from the corresponding haloheteroaromatics, reacted selectively with n-butyllithium to give the lithio derivatives. (C) 2001 Elsevier Science Ltd. All rights reserved.