(R)-4-(1-hydroxyethyl)benzoic acid | 125577-90-4

• 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: (R)-4-(1-hydroxyethyl)benzoic acid
• 英文别名: 4-[(1R)-1-hydroxyethyl]benzoic acid
• CAS: 125577-90-4
• 化学式: C₉H₁₀O₃
• 分子量: 166.177
• InChiKey: UBXQIJLWYJGCCO-ZCFIWIBFSA-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：

  (R)-4-(1-hydroxyethyl)benzoic acid 在 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.08h， 生成 (R)-1-(4-((2-((tert-butoxycarbonyl)amino)phenyl)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：

  4-乙酰基苯甲酸 在 吡啶 、 sodium tetrahydroborate 、 BES buffer 、 Lipase from Burkholderia cepacia 、 calcium chloride 作用下， 以 乙醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 51.0h， 生成 (R)-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

• Detection and Kinetic Characterization of a Highly Reactive Heme–Thiolate Peroxygenase Compound I
  作者：Xiaoshi Wang、Sebastian Peter、Matthias Kinne、Martin Hofrichter、John T. Groves

  DOI：10.1021/ja3049223

  日期：2012.8.8

  The second-order rate constant for AaeAPO-I formation was 1.0 (±0.4) × 10(7) M(-1) s(-1) at pH 5.0, 4 °C. The relatively slow decomposition rate, 1.4 (±0.03) s(-1), allowed the measurement of its reactivity toward a panel of substrates. The observed rate constants, k2', spanned 5 orders of magnitude and correlated linearly with bond dissociation enthalpies (BDEs) of strong C-H bond substrates with a

  来自 Agrocybe aegerita (AaeAPO) 的细胞外血红素硫醇过氧化酶已被证明可以使用过氧化氢作为末端氧化剂羟基化烷烃和许多其他底物。我们描述了 AaeAPO 化合物 I 在与 mCPBA 反应时的形成和分解动力学。AaeAPO-I (361, 694 nm) 的紫外-可见光谱特征类似于氯过氧化物酶-I 和最近描述的细胞色素 P450-I。AaeAPO-I 形成的二级速率常数为 1.0 (±0.4) × 10(7) M(-1) s(-1)，pH 5.0，4 °C。相对较慢的分解速率为 1.4 (±0.03) s(-1)，允许测量其对一组基板的反应性。观察到的速率常数，k2'，跨越 5 个数量级，并与强 CH 键底物的键解离焓 (BDE) 线性相关，log k2' 与 BDE 的斜率约为 0.4。然而，羟基化速率对低于 90 kcal/mol 的 CH BDE 不敏感，类似于
• An Enantioconvergent Benzylic Hydroxylation Using a Chiral Aryl Iodide in a Dual Activation Mode
  作者：Ayham H. Abazid、Nils Clamor、Boris J. Nachtsheim

  DOI：10.1021/acscatal.0c02321

  日期：2020.8.7

  chiral iodoarene in a direct enantioselective hydroxylation of alkyl arenes is reported. This method allows the rapid synthesis of chiral benzyl alcohols in high yields and stereocontrol, despite its nontemplated nature. In a cascade activation consisting of an initial irradiation-induced radical C–H-bromination and a consecutive enantioconvergent hydroxylation, the iodoarene catalyst has a dual role. It

  据报道三唑取代的手性碘芳烃在烷基芳烃的直接对映选择性羟基化中的应用。尽管其非模板性质，该方法仍能以高产率和立体控制快速合成手性苄醇。在由初始辐射诱导的自由基C-H-溴化和连续的对映体会聚羟基化组成的级联活化中，碘芳烃催化剂具有双重作用。它通过原位形成的溴碘烷引发处于氧化态的自由基溴化反应，在第二步（铜催化）中，它起手性配体的作用。这项工作证明了手性芳基碘化物催化剂在高对映选择性的C-H活化转化中既起氧化剂的作用，又起手性配体的作用。此外，
• TAKEHXARA, SADAO;SEDZI, TADAO;OSAVA, MASASI;OGAVA, XIROSI;FUDZISAVA, NOBU+
  作者：TAKEHXARA, SADAO、SEDZI, TADAO、OSAVA, MASASI、OGAVA, XIROSI、FUDZISAVA, NOBU+

  DOI：——

  日期：——
• US6720439B1
  申请人：——

  公开号：US6720439B1

  公开（公告）日：2004-04-13
• 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.