(2S,3S)-1,4-bis(2-methoxyphenyl)-2,3-butanediol | 239090-01-8

• 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(2-methoxyphenyl)-2,3-butanediol
• 英文别名: (2S,3S)-1,4-di(2-methoxyphenyl)-2,3-butanediol；(S,S)-1,4-bis(2-methoxyphenyl)-2,3-butanediol；(2S,3S)-1,4-bis(2-methoxyphenyl)butane-2,3-diol
• CAS: 239090-01-8
• 化学式: C₁₈H₂₂O₄
• 分子量: 302.37
• InChiKey: MPJXXBNMPKXPAA-HOTGVXAUSA-N

物化性质

• 沸点：
  490.1±40.0 °C(Predicted)
• 密度：
  1.164±0.06 g/cm3(Predicted)

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(2-methoxyphenyl)-2,3-butanediol 在 对甲苯磺酸 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 368.0h， 生成 methyl (2S,3S,3aR)-2-[1,1-[(2S,3S)-1,4-bis(2-methoxyphenyl)-2,3-butylenedioxy]ethyl]hexahydro-2H-isoxazolo[2,3-a]pyridine-3-carboxylate
  参考文献：
  名称：

  Acetals of γ-oxo-α,β-unsaturated esters in nitrone cycloadditions. Regio- and stereochemical implications

  摘要：

  Several acetals of gamma -oxo-alpha,beta -unsaturated esters have been prepared, mainly from enantiopure C-2-symmetric diols, and their 1,3-dipolar cycloaddition to 2,3,4,5-tetrahydropyridine 1-oxide has been studied. All the reactions showed complete regio selectivity and a high preference for the endo approach of the reactants in the transition state. The enantiopure acetals derived from (cis, cis) -spiro [4.4]nonane- 1, 6-diol gave the highest diastereofacial selectivity. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00294-4
• 作为产物：
  描述：

  (2S)-2-[(2S)-环氧乙烷-2-基]环氧乙烷 、 2-Methoxyphenylmagnesium bromide 在 copper(l) iodide 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 以68%的产率得到(2S,3S)-1,4-bis(2-methoxyphenyl)-2,3-butanediol
  参考文献：
  名称：

  Synthesis of new enantiomerically pure monoketals of p-benzoquinone with C2-symmetry

  摘要：

  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.

  DOI：

  10.1016/s0040-4020(99)00400-7

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.