4-(2-(1,1'-联苯基)-4-基乙氧基)-8-氟喹唑啉 | 131147-14-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 4-(2-(1,1'-联苯基)-4-基乙氧基)-8-氟喹唑啉
• 英文名称: 2,4,5,6-tetra-O-benzyl-DL-myo-inositol
• 英文别名: (+/-)-1,3,4,5-tetra-O-benzyl-myo-inositol；DL-1,3,4,5-tetrakis-O-benzyl-myo-inositol；DL-1,3,4,5-Tetra-O-benzyl-myo-inositol；1D-1,3,5,6-tetra-O-benzyl-myo-inositol；1,3,4,5-tetra-O-benzyl-L-myo-inositol
• CAS: 131147-14-3；131233-76-6；132746-98-6；132747-00-3；141040-63-3；145553-67-9
• 化学式: C₃₄H₃₆O₆
• 分子量: 540.656
• InChiKey: XGMQKZYVODIFBY-GEPQNFMVSA-N

物化性质

• 沸点：
  680.9±55.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.06
• 重原子数：
  40.0
• 可旋转键数：
  12.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  77.38
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  4-(2-(1,1'-联苯基)-4-基乙氧基)-8-氟喹唑啉 在 吡啶 、 二乙胺基三氟化硫 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成 (+)-1D-1,3,5,6-Tetra-O-benzyl-4-deoxy-4-fluoro-myo-inositol (S)-camphanate
  参考文献：
  名称：

  Offer, John L.; Voorheis, H. Paul; Metcalfe, James C., Journal of the Chemical Society. Perkin transactions I, 1992, # 8, p. 953 - 960

  摘要：

  DOI：
• 作为产物：
  描述：

  (3aS,4R,5R,6S,7R,7aR)-6,7-Bis-allyloxy-2,2-dimethyl-hexahydro-benzo[1,3]dioxole-4,5-diol 在 palladium on activated charcoal 盐酸 、 四丁基溴化铵 、 sodium hydride 、 二正丁基氧化锡 、 对甲苯磺酸 作用下， 以 甲醇 、 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.5h， 生成 4-(2-(1,1'-联苯基)-4-基乙氧基)-8-氟喹唑啉
  参考文献：
  名称：

  The synthesis and resolution of (±)-1,5,6-tri-O-benzyl-myo-inositol

  摘要：

  Racemic 1,5,6-tri-O-benzyl-myo-inositol was prepared by five routes and converted into 1,5,6-tri-O-benzyl-2,3-O-isopropylidene-myo-inositol, the camphanates of which were readily separated by chromatography. The absolute configurations of the chiral derivatives were established by their conversion into the known chiral 1,4,5,6-tetra-O-benzyl-myo-inositols. 1D-1,5,6-Tri-O-benzyl-2,3-O-isopropylidene-myo-inositol was converted into 1D-1,3,5,6-tetra-O-benzyl-myo-inositol and thence into 1D-2,4-di-O-methyl-myo-inositol. 1D-1,5,6-Tri-O-benzyl-myo-inositol was converted into 1D-1,2,5,6-tetra-O-benzyl-myo-inositol, the diacetate of which is a chiral analogue of "thermosalient crystals". The potential of the above compounds for the synthesis of natural products is surveyed.

  DOI：

  10.1016/0008-6215(90)80132-m

文献信息

• Dimethyltin Dichloride Catalyzed Regioselective Alkylation of<i>cis</i>-1,2-Diols at Room Temperature
  作者：Varma Saikam、Saidulu Dara、Mahipal Yadav、Parvinder Pal Singh、Ram A. Vishwakarma

  DOI：10.1021/acs.joc.5b01898

  日期：2015.12.18

  mild and general method for the regioselective installation of benzyl, allyl, para-methoxybenzyl and naphthyl groups on cis-1,2-diols. The optimized method operates at room temperature using dimethyltin dichloride as catalyst and silver oxide as an additive. The present method works well with both sugars (such as mono- and disaccharides) and nonsugars (such as inositols, propan-1,2-diol, 1,2-cycloalkanediols

  在这里，我们已经开发出一种温和的通用方法，用于在顺式-1，2-二醇上区域选择性地安装苄基，烯丙基，对甲氧基苄基和萘基。该优化方法在室温下使用二氯化二甲基锡作为催化剂，氧化银作为添加剂进行操作。本方法对于糖类（例如单糖和二糖）和非糖类（例如肌醇，1，2-丙二醇，1,2-环烷二醇和脱水赤藓糖醇）均适用，并且还提供了相对更好的官能团相容性。
• Relative reactivity of hydroxyl groups in inositol derivatives: role of metal ion chelation
  作者：Subramanian Devaraj、Rajendra C. Jagdhane、Mysore S. Shashidhar

  DOI：10.1016/j.carres.2009.04.007

  日期：2009.7

  one hydroxyl group via their alkali metal alkoxides (sodium or lithium) preferentially occurs at a hydroxyl group having a vicinal cis-oxygen atom. In general the observed selectivity is relatively higher for lithium alkoxides than for the corresponding sodium alkoxide. The observed regioselectivity is also dependent on other factors such as the solvent and reaction temperature. A perusal of the results

  含有一个以上羟基的肌醇衍生物经由其碱金属醇盐（钠或锂）的O-烷基化优先发生在具有邻位顺式氧原子的羟基上。通常，观察到的对于烷氧基锂的选择性比对相应的烷氧基钠的选择性更高。观察到的区域选择性还取决于其他因素，例如溶剂和反应温度。对本文提供的结果以及文献中提供的结果的仔细研究表明，肌醇衍生物对金属离子的螯合在观察到的区域选择性中起着重要作用。与反应的羟基的轴向或赤道位置有关的立体因素对这些O-烷基化反应的结果没有太大贡献。
• A More Convenient and General Procedure for <i>O</i>-Monobenzylation of Diols via Stannylenes:  A Critical Reevaluation of the Bu₂SnO Method
  作者：Alessandro B. C. Simas、Karla C. Pais、Angelo A. T. da Silva

  DOI：10.1021/jo026794c

  日期：2003.6.1

  A more consistent, straightforward, and economical protocol for generation of stannylene species and their reaction with BnBr leading to products of O-monobenzylation of diols has been set. It has shown to be specially indicated for substrates bearing vicinal trans 1,2-diol moieties on cyclohexane backbones, which are more resistant to these transformations. Such protocol has been successfully applied to myo-inositol derivatives and acyclic diols.
• Direct selective and controlled protection of multiple hydroxyl groups in polyols via iterative regeneration of stannylene acetals
  作者：Alessandro B.C. Simas、Angelo A.T. da Silva、Tarcizio J. dos Santos Filho、Pedro T.W. Barroso

  DOI：10.1016/j.tetlet.2009.03.114

  日期：2009.6

  A direct selective protection (O-benzylation) of two or more hydroxyl groups in polyols displaying diverse Structural patterns was made possible by the establishment of conditions that enable an efficient turnover for the Bu2Sn group, initially at the corresponding stannylene acetals (only similar to 1.0 mol equiv of Bu2SnO was employed). It was also demonstrated that one might exert control over the number of protected groups, by means of appropriate tuning of reaction conditions. The feasibility of a substoichiometric (tin source) catalytic protocol was demonstrated as well. (C) 2009 Elsevier Ltd. All rights reserved.