(R)-2-(Benzyloxy)butane-1,4-diol | 123394-80-9

• 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)-2-(Benzyloxy)butane-1,4-diol
• 英文别名: (R)-2-benzyloxy-1,4-butanediol；(2R)-2-(benzyloxy)-1,4-butanediol；(2S)-2-phenylmethoxybutane-1,4-diol；2-(benzyloxy) butane-1,4-diol；(2R)-benzyloxy-1,4-butanediol；(2R)-2-phenylmethoxybutane-1,4-diol
• CAS: 123394-80-9
• 化学式: C₁₁H₁₆O₃
• 分子量: 196.246
• InChiKey: XGFDEUXSUUXCNW-LLVKDONJSA-N

物化性质

• 沸点：
  365.8±27.0 °C(Predicted)
• 密度：
  1.130±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  14
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  49.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R)-2-(Benzyloxy)butane-1,4-diol 在 吡啶 、 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 16.5h， 生成 (2R)-2-(benzyloxy)-4-[N-(mesitylenesulfonyl)ethylamino]-O-tosyl-1-butanol
  参考文献：
  名称：

  Synthesis and Evaluation of Hydroxylated Polyamine Analogues as Antiproliferatives

  摘要：

  The synthesis of four hydroxylated polyamine analogues, (2R,10R)-N-1,N-11-diethyl-2,10-dihydroxynorspermine, droxynorspermine, (2S,10S)-N-1,N-11-diethyl-2,10-dihydroxynospermine, (3S, 12S)-N-1,N-14-diethyl-3, 12-dihydroyhomospermine, and (3R,12R)-N-1-N-14-diethyl-3,12-dihgrdroxyhomospermine, is described along with their impact on the growth and polyamine metabolism of L1210 murine leukemia cells. Four different synthetic approaches are set forth, two each for the hydroxylated norspermines and for the hydroxylated homospermines. The key step in the assembly of the norspermines was the coupling of either N-[2R)-2,3-epoxypropyl]-N-ethyl p-toluenesulfonamide or N-[(2S)-2, 3-epoxypropyl]-N-ethyl trifluoromethane sulfonamide to N,N'-dibenzyl-1,3-diaminopropane. The key step with homospermines employed alkylation of putrescine with (3S)-N-(benzyloxycarbonyl)-N-ethyl-3,4-epoxybutylamine or of N,N'-bis(mesitylenesulfonyl)-1,4-butanediamine with (2R)-2-benzyloxy-4-[N-(mesitylenesulfonyl], All of the hydroxylated analogues were active against L1210 cells with 96-h IC50 values of less than or equal to 2 mu M, and they also effectively reduced putrescine and spermidine, although the effect on spermine pools ranged from moderate to insignificant. Interestingly, the impact of the hydroxylated analogues an ornithine decarboxylase (ODC) was significantly less than that of unhydroxylated parent drug (e.g., (NN11)-N-1-diethylnorspermine [DENSPM]) at 1 mu M ; however, S-adenosylmethionine decarboxylase (AdoMetDC) depletion was nearly identical to what was observed in cells treated with parent drug. The most notable difference between the parent and hydroxylated analogues was seen with spermidine/spermine N-1-acetyltransferase (SSAT) upregulation in the DENSPM series. The hydroxylated analogues, especially (R,R)-(HO)(2)-DENSPM, were much less effective at upregulation than the parent DENSPM. Finally, a comparison of the toxicity of (RP)-(HO)(2)DENSPM with that of DENSPM at subchronic doses revealed that the neurological effects seen with DENSPM were now absent.

  DOI：

  10.1021/jm990375z
• 作为产物：
  描述：

  (4S,5R,2'R)-1,5-dimethyl-4-phenyl-3-(2'-benzyloxy-5'-methyl-5'-hexenoyl)imidazolidin-2-one 在 sodium tetrahydroborate 、 锂硼氢 、 二甲基硫 、 臭氧 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 生成 (R)-2-(Benzyloxy)butane-1,4-diol
  参考文献：
  名称：

  通过手性乙醇酸酯酰亚胺的烷基化对映选择性合成2-苄氧基醇和1,2-二醇。旋光甘油衍生物的简便方法

  摘要：

  乙醇酸酯酰亚胺2a和2b的手性烯酸酯的烷基化以高度非对映选择性的方式进行，以高收率得到2′-取代的产物。用LiBH 4还原裂解得到相应的2-苄氧基醇3a-c和11a-b，它们以高光学纯度连续转化为1,2-二醇。通过这种方法，从2a和2b开始合成了从海绵Plocamiidae提取的甘油酯（R）-1-丙酰氧基-2、3-丙二醇9和（S）-1-十三烷氧基-2,3-丙二醇14，分别。

  DOI：

  10.1016/0040-4020(89)80148-6

文献信息

• Bifunctional TEMPO-electrocatalysts enabled enantioselective oxidative lactonization of 1,4-diols
  作者：Pei-Sen Gao、Chang-Wang Pan、Cheng Liu、Wen-Tong Chen

  DOI：10.1016/j.mcat.2023.113663

  日期：2024.1

  resolution of racemic 1,4-diols, affording diverse chiral 1,4-diols and γ-lactones with good or excellent chemo-, regio, and enantioselectivity. We also show that this cooperative Cu/TEMPO-BOX catalytic strategy is applicable to the electro-oxidative kinetic resolution of 1,2- and 1,3-amino alcohols. This work demonstrates the potential of bifunctional electrocatalysis for asymmetric synthetic methods and

  不对称电催化有望为获得对映体富集分子提供独特的途径，而这些分子很难通过更传统的方法获得，但开发能够进行高度对映选择性转化的高效电催化剂仍然难以实现。为了实现这一令人羡慕的目标，需要能够介导氧化还原和提供高立体控制的双功能电催化剂。在这里，我们公开了一种新型 TEMPO-BOX 连接的铜电催化剂，能够氧化动力学拆分外消旋 1,4-二醇，提供具有良好或优异的化学选择性、区域选择性和对映选择性的多种手性 1,4-二醇和 γ-内酯。我们还表明，这种协同 Cu/TEMPO-BOX 催化策略适用于 1,2- 和 1,3- 氨基醇的电氧化动力学拆分。这项工作展示了双功能电催化在不对称合成方法中的潜力，我们预计它将刺激新型混合电催化剂的开发，以实现新颖的不对称电催化方法。
• Investigating the role of the hydroxyl groups of substrate erythrose 4-phosphate in the reaction catalysed by the first enzyme of the shikimate pathway
  作者：David Tran、Amy L. Pietersma、Linley R. Schofield、Matthias Rost、Geoffrey B. Jameson、Emily J. Parker

  DOI：10.1016/j.bmcl.2011.09.017

  日期：2011.11

  3-Deoxy-D-arabino-heptulosonate 7-phosphate (DAH7P) synthase catalyses the first step of the shikimate pathway, which is responsible for the biosynthesis of aromatic amino acids in microorganisms and plants. This enzyme catalyses an aldol reaction between phosphoenolpyruvate and D-erythrose 4-phosphate to generate DAH7P. Both 2-deoxyerythrose 4-phosphate and 3-deoxyerythrose 4-phosphate were synthesised and tested as alternative substrates for the enzyme. Both compounds were found to be substrates for the DAH7P synthases from Escherichia coli, Pyrococcus furiosus and Mycobacterium tuberculosis, consistent with an acyclic mechanism for the enzyme for which neither C2 nor C3 hydroxyl groups are required for catalysis. The enzymes all showed greater tolerance for the loss of the C2 hydroxyl group than the C3 hydroxyl group. (C) 2011 Elsevier Ltd. All rights reserved.
• Regio- and enantioselective properties of the lipase-catalyzed irreversible transesterification of some 2-substituted-1,4-butanediols in organic solvents
  作者：Patrizia Ferraboschi、Silvana Casati、Elisa Verza、Enzo Santaniello

  DOI：10.1016/0957-4166(95)00116-7

  日期：1995.5

  The regioselectivity of the Pseudomonas fluorescens (P. cepacia) lipase (PFL)-catalyzed irreversible transesterification of 2-substituted-1,4-butanediols 1a-3a has been studied and, in the case of 3a, it has been shown that (R)- and (S)-diols are acylated with opposite regioselectivity.
• Regioselective Transformation of Malic Acid: A Practical Method for the Construction of Enantiomerically Pure Indolizidines
  作者：Peter Gmeiner、Dagmar Junge

  DOI：10.1021/jo00117a052

  日期：1995.6
• CARDILLO, GIULIANA;ORENA, MARIO;ROMERO, MARTA;SANDRI, SERGIO, TETRAHEDRON, 45,(1989) N, C. 1501-1508
  作者：CARDILLO, GIULIANA、ORENA, MARIO、ROMERO, MARTA、SANDRI, SERGIO

  DOI：——

  日期：——