1-benzyloxy-3-(p-methoxybenzyloxy)propan-2-ol | 162427-33-0

• 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: 1-benzyloxy-3-(p-methoxybenzyloxy)propan-2-ol
• 英文别名: 1-Benzyloxy-3-[(4-methoxyphenyl)methoxy]propan-2-ol；1-[(4-methoxyphenyl)methoxy]-3-phenylmethoxypropan-2-ol
• CAS: 162427-33-0
• 化学式: C₁₈H₂₂O₄
• 分子量: 302.37
• InChiKey: SDVLJRAVKFCRPY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  22
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  47.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-benzyloxy-3-(p-methoxybenzyloxy)propan-2-ol 在 N-溴代丁二酰亚胺(NBS) 、 4 A molecular sieve 、 sodium hydride 、 sodium iodide 作用下， 以 四氢呋喃 、 二氯甲烷 、 paraffin 为溶剂， 反应 0.5h， 生成 (R,S)-1-<(1-benzyloxy-3-(p-methoxybenzyloxy)-2-propoxy)methyl>thymine
  参考文献：
  名称：

  Synthesis and Antiviral Study of Acyclic Analogs of 3′-Azido, 3′-Amino, and 3′-Fluoro-3′-deoxythymidine, and of HEPT analogs

  摘要：

  几种新的无环核苷酸已从外消旋氯氢醇或外消旋氟氢醇中合成。该过程涉及环氧化物的开环，然后与碘甲基苯硫醚进行链延伸，接着将苯硫乙缩醛与胸腺嘧啶偶联。去保护后得到标题化合物6、8和18，而在C-6位置引入苯硫基团则生成了三种HEPT类似物，13、19和24。

  DOI：

  10.1055/s-1994-25609
• 作为产物：
  描述：

  4-甲氧基氯苄 在 lithium perchlorate 、 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 169.0h， 生成 1-benzyloxy-3-(p-methoxybenzyloxy)propan-2-ol
  参考文献：
  名称：

  Synthesis of 2,5-dihydrofurans via alkylidene carbene insertion reactions

  摘要：

  已证明，烷叉亚甲基卡宾的插入反应是合成2,5-二氢呋喃环体系的有效方法。在含有吸电子取代基的底物上获得了最佳结果，这些底物似乎不太容易发生竞争性的重排反应。这一认识促进了合成角鲨烯内酯-扎戈唑酸天然产物核心结构新方法的发展。

  DOI：

  10.1039/b111097g

文献信息

• Conformationally constrained analogues of diacylglycerol (DAG). 14.1 Dissection of the roles of the sn-1 and sn-2 carbonyls in DAG mimetics by isopharma cophore replacement
  作者：Victor E. Marquez、Rajiv Sharma、Shaomeng Wang、Nancy E. Lewin、Peter M. Blumberg、In-Sik Kim、Jeewoo Lee

  DOI：10.1016/s0960-894x(98)00307-2

  日期：1998.7

  The replacement of the sn-l and sn-2 carbonyl esters in DAG-surrogate lactones by sulfonate esters showed that their isosteric properties in protein kinase C binding are controlled by the location of the hydrophobic alkyl chain on the molecule. The CO and SO2 groups appear to be true isosteres only when they are adjacent to the alkyl chain, which is presumed to insert normal to the lipid bilayer. Published by Elsevier Science Ltd.
• 5-Acyloxy-5-hydroxymethyltetrahydro-2-furancarboxylate as a novel template for protein kinase C (PKC) binding
  作者：Jeewoo Lee、Kee-Chung Han、Sang-Yoon Lee、Su-Yeon Kim、Ji-Hye Kang、Nancy E. Lewin、Lionel S. Best、Peter M. Blumberg、Victor E. Marquez

  DOI：10.1016/s0014-827x(01)01077-1

  日期：2001.4

  A series of alkyl tetrahydrofuran-2-carboxylates (1-4) bearing a new set of three pharmacophoric groups were tested as protein kinase C (PKC) ligands. The compounds were synthesized from commercially available glycidyl 4-methoxyphenyl ether. The correlation between their binding affinities for PKC-alpha and a conformational fit to phorbol ester indicates they mimic a pharmacophore model comprising the C-20-OH, C-3-C=O and C-9-OH rather than that including the C-13-C=O moiety. (C) 2001 Elsevier Science S.A. All rights reserved.
• The scope and limitation of the regio- and enantioselective hydrolysis of aliphatic epoxides using Bacillus subtilis epoxide hydrolase, and exploration toward chirally differentiated tris(hydroxymethyl)methanol
  作者：Ken-ichi Shimizu、Maki Sakamoto、Manabu Hamada、Toshinori Higashi、Takeshi Sugai、Mitsuru Shoji

  DOI：10.1016/j.tetasy.2010.07.014

  日期：2010.8

  The substrate specificity of an engineered Bacillus subtilis epoxide hydrolase, which so far had shown high activity and enantioselectivity with 1-benzyloxymethyl-1 -methyloxirane, has been studied by altering the methyl substituent into hydrogen, oxygen-containing functionalities, and unsaturated homologs. High enantioselectivity (E = 44) was observed with 1-benzyloxymethyl-1-vinyloxirane with a proper catalytic activity. The elaboration of the reaction conditions and work-up procedures enabled a preparative-scale kinetic resolution, to give (R)-2-benzyloxymethyl-3-butene-1,2-diol and its antipodal (R)-epoxide in high ees. (C) 2010 Elsevier Ltd. All rights reserved.
• Facile chelation-controlled reductive opening of methoxybenzylidene acetals with Bu3SnH and MgBr2. Regioselective protection strategy as MPM ethers
  作者：Bao-Zhong Zheng、Megumi Yamauchi、Hiroo Dei、Shin-ichi Kusaka、Katsuya Matsui、Osamu Yonemitsu

  DOI：10.1016/s0040-4039(00)01017-0

  日期：2000.8

  A mild and efficient regioselective reductive opening of methoxybenzylidene acetals using a combination of Bu3SnH and MgBr2. OEt2, mainly via five-membered chelation intermediates is described. This reaction was applied to synthetic intermediates of myriaporon and tedanolide. (C) 2000 Elsevier Science Ltd. All rights reserved.
• Synthesis of 2,5-dihydrofurans via alkylidene carbene insertion reactions
  作者：Louise F. Walker、Ahmed Bourghida、Stephen Connolly、Martin Wills

  DOI：10.1039/b111097g

  日期：2002.3.25

  The insertion reaction of alkylidene carbenes is demonstrated to be an effective method for the synthesis of 2,5-dihydrofuran ring systems. The best results have been obtained on substrates containing electron-withdrawing substituents, which appear less prone to the competing rearrangement reaction. This insight has led to the development of a new method for the synthesis of the core structure of the squalestatin–zaragozic acid natural products.

  已证明，烷叉亚甲基卡宾的插入反应是合成2,5-二氢呋喃环体系的有效方法。在含有吸电子取代基的底物上获得了最佳结果，这些底物似乎不太容易发生竞争性的重排反应。这一认识促进了合成角鲨烯内酯-扎戈唑酸天然产物核心结构新方法的发展。