(2S,3S)-1,4-bis(4-methoxyphenyl)-2,3-butanediol | 239090-00-7

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物
• 英文名称: (2S,3S)-1,4-bis(4-methoxyphenyl)-2,3-butanediol
• 英文别名: (1S,2S)-1,2-bis(p-methoxybenzyl)ethyleneglycol；(2S,3S)-1,4-di(4-methoxyphenyl)-2,3-butanediol；(2S,3S)-1,4-bis(4-methoxyphenyl)butane-2,3-diol
• CAS: 239090-00-7
• 化学式: C₁₈H₂₂O₄
• 分子量: 302.37
• InChiKey: UKELBQLJXCICKC-ROUUACIJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 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：

  (2S,3S)-1,4-bis(4-methoxyphenyl)-2,3-butanediol 在 四丁基氟化铵 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 15.0h， 生成 (4S,5S)-2-fluoro-4,5-bis[(4-methoxyphenyl)methyl]-1,3,2-dioxaborolane
  参考文献：
  名称：

  Use of chiral B(III) complexes in the cycloaddition of C,N-diphenylnitrone to tert-butyl vinyl ether

  摘要：

  The 1,3-dipolar cycloaddition of C,N-diphenylnitrone to tert-butyl vinyl ether in the presence of several chiral B(III) complexes which incorporate different bidentate ligands has been investigated. The use of these B(III) species reverses the endo/exo diastereoselectivity in relation to the uncatalysed reaction, giving trans cycloadducts as major products. Some of the catalysts gave very fast and high yielding reactions, but the enantioselectivities were only low to moderate. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(00)00405-5
• 作为产物：
  描述：

  cis-2,3-bis(4-methoxybenzyl)oxirane 在 硫酸 作用下， 反应 72.0h， 以0.035 g的产率得到(2S,3S)-1,4-bis(4-methoxyphenyl)-2,3-butanediol
  参考文献：
  名称：

  Ring-opening reactions of cis- and trans-2,3-bis(4-methoxybenzyl)oxirane: competition between assistance by and migration of anti aryl group

  摘要：

  DOI：

  10.1021/jo00364a026

文献信息

• The attempted stereoselective synthesis of chiral 2,2′-biindoline
  作者：Mary J. Gresser、Steven M. Wales、Paul A. Keller

  DOI：10.1016/j.tet.2010.06.035

  日期：2010.8

  The attempted first stereoselective synthesis of 2,2'-biindoline using a metathesis-Sharpless asymmetric dihydroxylation strategy results in the synthesis of the heterocycle in poor to modest stereoselectivity. Attempts to improve the ee by varying the heteroatom protecting groups in key intermediates did not enhance the outcome of the Sharpless AD reaction. Therefore a limitation of this AD reaction is the use of 1,4-substituted but-2-enes where these substituents are ortho-substituted aromatics. Crown Copyright (C) 2010 Published by Elsevier Ltd. All rights reserved.
• Synthesis of new enantiomerically pure monoketals of p-benzoquinone with C2-symmetry
  作者：Pedro de March、Marta Figueredo、Josep Font、Jordi Medrano

  DOI：10.1016/s0040-4020(99)00400-7

  日期：1999.6

  Several new monoketals of p-benzoquinone with the structure of 1,3-dioxaspiro[4.5]deca-6,9-dien-8-one have been synthesised in enantiopure form by the straightforward reaction of the quinone with secondary C-2-symmetric 1,2-diols. The preparation of two new enantiopure C-2-1,2-glycolsis also reported. (C) 1999 Elsevier Science Ltd. All rights reserved.
• Use of chiral B(III) complexes in the cycloaddition of C,N-diphenylnitrone to tert-butyl vinyl ether
  作者：Pau Bayón、Pedro de March、Marta Figueredo、Josep Font、Jordi Medrano

  DOI：10.1016/s0957-4166(00)00405-5

  日期：2000.11

  The 1,3-dipolar cycloaddition of C,N-diphenylnitrone to tert-butyl vinyl ether in the presence of several chiral B(III) complexes which incorporate different bidentate ligands has been investigated. The use of these B(III) species reverses the endo/exo diastereoselectivity in relation to the uncatalysed reaction, giving trans cycloadducts as major products. Some of the catalysts gave very fast and high yielding reactions, but the enantioselectivities were only low to moderate. (C) 2000 Elsevier Science Ltd. All rights reserved.
• Ring-opening reactions of cis- and trans-2,3-bis(4-methoxybenzyl)oxirane: competition between assistance by and migration of anti aryl group
  作者：Paolo Crotti、Maria Ferretti、Franco Macchia、Annalisa Stoppinoni

  DOI：10.1021/jo00364a026

  日期：1986.7