2-(3,5-dimethoxybenzyl)propane-1,3-diol | 67194-88-1

• 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: 2-(3,5-dimethoxybenzyl)propane-1,3-diol
• 英文别名: 2-[(3,5-Dimethoxyphenyl)methyl]propane-1,3-diol
• CAS: 67194-88-1
• 化学式: C₁₂H₁₈O₄
• 分子量: 226.273
• InChiKey: SYINOGXZTPKMPW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  58.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(3,5-dimethoxybenzyl)propane-1,3-diol 生成 3-(3,5-dimethoxybenzyl)pentanedinitrile
  参考文献：
  名称：

  Studies on total synthesis of the olivomycins

  摘要：

  DOI：

  10.1021/jo00415a041
• 作为产物：
  描述：

  3,5-二甲氧基苄基氯 在 lithium aluminium tetrahydride 、 乙醇 、 sodium 作用下， 生成 2-(3,5-dimethoxybenzyl)propane-1,3-diol
  参考文献：
  名称：

  Studies on total synthesis of the olivomycins

  摘要：

  DOI：

  10.1021/jo00415a041

文献信息

• The construction of novel perylenequinone core via efficient synthesis of versatile ortho-naphthoquinone as a key intermediate
  作者：Beom-Tae Kim、Ho-Seok Kim、Woo Sung Moon、Ki-Jun Hwang

  DOI：10.1016/j.tet.2009.03.057

  日期：2009.6

  The novel perylenequinone core, 1,12-diacetonitrile-3,10-perylenequinone, was successfully prepared from the dimerization of the key intermediate, 3-acetonitrile-1,2-naphthoquinone, which was synthesized by an efficient synthetic route in relatively short reaction steps (seven steps) and satisfactory overall yield. The perylenequinone core containing the acetonitrile functionality is notable in the

  通过关键中间体3-乙腈-1,2-萘醌的二聚反应成功地合成了新颖的per醌核心1,12-二乙腈-3,10-per醌，该中间体是通过有效的合成路线在较短的时间内合成的步骤（七个步骤）和令人满意的总产量。含有乙腈官能团的per醌核心很显着，因为通用乙腈基团可在以后的合成阶段用于制备各种化合物，以开发新的和新颖的per醌衍生物作为潜在的光动力剂。
• Insights into the Solvent Dependence of Chymotryptic Prochiral Selectivity
  作者：Tao Ke、Alexander M. Klibanov

  DOI：10.1021/ja9802201

  日期：1998.5.1

  In a previous publication (Ke, T.; Wescott, C. R.; Klibanov, A. M. J. Am. Chem. Soc. 1996, 118, 3366−3374), we discovered and rationalized mechanistically a marked solvent dependence of chymotrypsin's prochiral selectivity in the acylation of 2-(3,5-dimethoxybenzyl)-1,3-propanediol with vinyl acetate. In this study, we have answered several important unresolved questions concerning that phenomenon

  在之前的出版物 (Ke, T.; Wescott, CR; Klibanov, AMJ AM. Chem. Soc. 1996, 118, 3366−3374) 中，我们发现并在机械上合理化了糜蛋白酶在 2 酰化中的前手性选择性的显着溶剂依赖性-(3,5-二甲氧基苄基)-1,3-丙二醇与乙酸乙烯酯。在这项研究中，我们回答了有关该现象的几个重要的未解决问题。已经发现前手性选择性的溶剂依赖性由 (kcat/KM)pro-R 支配，并且这一发现已在 pro-R 和 pro-S 过渡态的计算机建模分析的基础上得到解释结构。溶剂引起的 kcat/KM 值变化与 kcat 或 KM 单独变化之间没有相关性，大概反映了后两个参数的复杂性。最后，
• Prediction of the Solvent Dependence of Enzymatic Prochiral Selectivity by Means of Structure-Based Thermodynamic Calculations
  作者：Tao Ke、Charles R. Wescott、Alexander M. Klibanov

  DOI：10.1021/ja952674t

  日期：1996.1.1

  A new, quantitative model is elaborated to rationalize the solvent dependence of enzymatic selectivity solely on the basis of the thermodynamics of substrate solvation. The model predicts that any type of the selectivity (defined as the ratio of k(cat)/K-M values) should be proportional to the ratio of the thermodynamic activity coefficients of the desolvated portions of the substrate(s) in the relevant transition state of the enzymatic reaction. The latter ratio is calculated by (i) determining the desolvated portion of the substrate in the transition state using molecular modeling based on the crystal structure of the enzyme, (ii) approximating this desolvated portion of the substrate by a distinct model compound, and (iii) calculating the activity coefficient of this model compound using the UNIFAC computer algorithm. In this study, the developed general model has been applied to, and verified with, prochiral selectivity of enzymes. Crystals (lightly cross-linked with glutaraldehyde) of gamma-chymotrypsin or subtilisin Carlsberg used as asymmetric catalysts in organic solvents almost quantitatively adhere to the predictions of the model in the acetylation of 2-substituted 1,3-propanediols. In contrast, little agreement between the predicted and observed solvent dependences of the prochiral selectivity has been obtained with lyophilized or acetone-precipitated chymotrypsin, thus confirming that the enzyme structure in such preparations (but not in crystals) is non-native.