(S)-4-(1-hydroxyethyl)benzoic acid | 125577-89-1

• 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: (S)-4-(1-hydroxyethyl)benzoic acid
• 英文别名: 4-(1-Hydroxyethyl)benzoic acid, (S)-；4-[(1S)-1-hydroxyethyl]benzoic acid
• CAS: 125577-89-1
• 化学式: C₉H₁₀O₃
• 分子量: 166.177
• InChiKey: UBXQIJLWYJGCCO-LURJTMIESA-N

物化性质

• 沸点：
  336.6±25.0 °C(Predicted)
• 密度：
  1.249±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-4-(1-hydroxyethyl)benzoic acid 在 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.08h， 生成 (S)-1-(4-((2-aminophenyl)carbamoyl)phenyl)ethyl 2-((S)-4-(4-chlorophenyl)- 2,3,9-trimethyl-6H-thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepin-6-yl)acetate
  参考文献：
  名称：

  WO2024123929A1

  摘要：

  公开号：
• 作为产物：
  描述：

  1-(4-甲基苯基)-1-乙醇 在 吡啶 、 BES buffer 、 subtilisin BPN' 、 calcium chloride 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 48.0h， 生成 (S)-4-(1-hydroxyethyl)benzoic acid
  参考文献：
  名称：

  How Substrate Solvation Contributes to the Enantioselectivity of Subtilisin toward Secondary Alcohols

  摘要：

  The current rule to predict the enantiopreference of subtilisin toward secondary alcohols is based on the size of the substituents at the stereocenter and implies that the active site contains two differently sized pockets for these substituents. Several experiments are inconsistent with the current rule. First, the X-ray structures of subtilisin show there is only one pocket (the S1' pocket) approximately the size of a phenyl group to bind secondary alcohols. Second, the rule often predicts the incorrect enantiomer for reactions in water. To resolve these contradictions, we refine the current rule to show that subtilisin binds only one substituent of a secondary alcohol and leaves the other in solvent. To test this refined empirical rule, we show that the enantioselectivity of a series of secondary alcohols in water varied linearly with the difference in hydrophobicity (log P/P0) of the substituents. This hydrophobicity difference accounts for the solvation of one substituent in water.

  DOI：

  10.1021/ja0528937

文献信息

• Structural insights into the role of the acid-alcohol pair of residues required for dioxygen activation in cytochrome P450 enzymes
  作者：Tom Coleman、Jeanette E. Stok、Matthew N. Podgorski、John B. Bruning、James J. De Voss、Stephen G. Bell

  DOI：10.1007/s00775-020-01781-4

  日期：2020.6

  pronounced than reported with P450cam. Its crystal structures revealed fewer changes at the I-helix, compared to the P450cam system. The structural changes observed within the I-helix of P450cam during oxygen activation do not seem to be required in this P450. These differences are due to the presence of a second threonine residue at position 253, which is absent in P450cam. This threonine forms part

  细胞色素P450血红素单加氧酶通常在I螺旋内使用一对酸-醇残基来激活与铁结合的双氧。这项工作旨在澄清有关酒精功能在此过程中的重要性的相互矛盾的报道。制备了P450的突变体CYP199A4（CYP199A4 D251N和CYP199A4 T252A），表征并解析了其晶体结构。CYP199A4的酸残基不属于盐桥网络的一部分，这是范例模型系统P450cam的关键功能。取而代之的是通过水分子链直接质子传递网络延伸到表面。然而，CYP199A4 D251N大大降低了该酶的活性，与质子传递中的作用一致。CYP199A4 T252A降低了酶的偶联效率，同时增加了过氧化氢的解偶联途径。但是，这种突变的影响远不如P450cam报道的那么明显。与P450cam系统相比，其晶体结构在I螺旋处显示的变化更少。在此P450中似乎不需要在氧激活期间在P450cam的I螺旋内观察到的结构变化。这些差异是由于P450ca
• US6720439B1
  申请人：——

  公开号：US6720439B1

  公开（公告）日：2004-04-13
• [EN] PROCEDURE FOR THE ENANTIOSELECTIVE ADDITION OF ORGANOZINC COMPOUNDS TO COMPOUNDS DERIVED FROM ACETOPHENONES<br/>[ES] PROCEDIMIENTO PARA LA ADICIÓN ENANTIOSELECTIVA DE COMPUESTOS ORGANOZÍNCICOS A COMPUESTOS DERIVADOS DE ACETOFENONAS<br/>[FR] PROCÉDÉ D'ADDITION ÉNANTIOSÉLECTIVE DE COMPOSÉS ORGANOZINCIQUES À DES COMPOSÉS DÉRIVÉS D'ACÉTOPHÉNONES
  申请人：UNIV VALLADOLID

  公开号：WO2011073487A1

  公开（公告）日：2011-06-23

  Procedimiento de elevado rendimiento para la preparación de compuestos de formula (I) o una sal de los mismos, o cualquier forma enantiomerica sustancialmente pura de los mismos, que comprende la adición nucleofílica de compuestos organozincicos de formula (Rz)2Zn a compuestos formula (II) en presencia un compuesto de formula (III) que aporta enantioselectividad a la reacción de adición. La invención incluye también compuestos de formula (III) que permiten la obtención de dicho alto rendimiento a la vez que una mayor enantioselectividad.
• How Substrate Solvation Contributes to the Enantioselectivity of Subtilisin toward Secondary Alcohols
  作者：Christopher K. Savile、Romas J. Kazlauskas

  DOI：10.1021/ja0528937

  日期：2005.9.1

  The current rule to predict the enantiopreference of subtilisin toward secondary alcohols is based on the size of the substituents at the stereocenter and implies that the active site contains two differently sized pockets for these substituents. Several experiments are inconsistent with the current rule. First, the X-ray structures of subtilisin show there is only one pocket (the S1' pocket) approximately the size of a phenyl group to bind secondary alcohols. Second, the rule often predicts the incorrect enantiomer for reactions in water. To resolve these contradictions, we refine the current rule to show that subtilisin binds only one substituent of a secondary alcohol and leaves the other in solvent. To test this refined empirical rule, we show that the enantioselectivity of a series of secondary alcohols in water varied linearly with the difference in hydrophobicity (log P/P0) of the substituents. This hydrophobicity difference accounts for the solvation of one substituent in water.