(R)-1-(3,4,5-trimethoxyphenyl)-1-propanol

• 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)-1-(3,4,5-trimethoxyphenyl)-1-propanol
• 英文别名: (R)-1-(3,4,5-trimethoxyphenyl)propan-1-ol；(S)-1-(3,4,5-trimethoxyphenyl)propan-1-ol；(1R)-1-(3,4,5-trimethoxyphenyl)propan-1-ol
• 化学式: C₁₂H₁₈O₄
• 分子量: 226.273
• InChiKey: FLYMDKWKEGXJLA-SECBINFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  47.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  diethylzinc 、 3,4,5-三甲氧基苯甲醛 在 C₃₁H₃₁NO₃ 作用下， 以 正己烷 、 甲苯 为溶剂， 以43%的产率得到(R)-1-(3,4,5-trimethoxyphenyl)-1-propanol
  参考文献：
  名称：

  1,2,3,4-四氢异喹啉β-氨基醇催化二乙基锌向芳醛的对映选择性加成

  摘要：

  摘要研究了一种高效的新型手性1,2,3,4-四氢异喹啉催化剂1，用于将二乙基锌加成芳基醛。使用10 mol％的这种手性催化剂，在温和条件下，可以以高达87％的收率和99.5％ee的速率获得仲醇。

  DOI：

  10.1016/j.cclet.2009.11.046

文献信息

• New polymer anchored chiral amino oxazolines as effective catalysts for enantioselective addition of diethylzinc to aldehydes
  作者：Nadim S Shaikh、Vishnu H Deshpande、Ashutosh V Bedekar

  DOI：10.1016/s0040-4039(02)01139-5

  日期：2002.8

  The application of a new type of polymer anchored chiral amino-oxazolinyl ligand as catalyst for the enantioselective addition of diethylzinc to aldehydes is reported. The catalyst is effective at a low ligand concentration and can be reused with minimal loss of activity.

  报道了一种新型的聚合物锚定的手性氨基-恶唑啉基配体作为催化剂将二乙基锌对醛进行对映选择性加成的报道。该催化剂在低配体浓度下是有效的，并且可以在活性损失最小的情况下重复使用。
• A practical o-hydroxybenzylamines promoted enantioselective addition of dialkylzincs to aldehydes with asymmetric amplification
  作者：Gianni Palmieri

  DOI：10.1016/s0957-4166(00)00290-1

  日期：2000.8

  The addition of dialkylzincs to aldehydes is accelerated considerably by the presence of a catalytic amount of o-hydroxybenzylamine (R,R)-2e to give, after hydrolysis, the corresponding alcohol (S)-9 in good enantiomeric purity. The origins of the enantioselection have been elucidated. A strong positive nonlinear relationship was observed for the reaction enantioselectivity with the use of o-hydroxybenzylamine 2e, which is very accessible through a short stereoselective synthetic route. The enantiomeric purity of the product 9 is much higher than the d.e. of the chiral source 2e, and the rate of the enantioselective catalysis increases considerably with the increase of the d.e. of(R,R)-2e. (C) 2000 Elsevier Science Ltd. All rights reserved.
• 2-Pyridylsulfinamides as effective catalysts in the asymmetric alkylation of aldehydes with diethylzinc
  作者：Kavirayani R. Prasad、Omkar Revu

  DOI：10.1016/j.tet.2013.07.061

  日期：2013.9

  Chiral 2-pyridylsulfinamides were shown to be effective catalysts in the alkylation of aryl and alkyl aldehydes with diethylzinc providing the corresponding alcohols in excellent enantioselectivity. Sulfinamide catalysts possessing solitary chirality at the sulfur center produced the product phenethyl alcohol in good enantioselectivity. Diastereomeric sulfinamides possessing chirality at the carbon-bearing nitrogen and at the sulfur of the sulfinamide increased the enantioselectivity of the product alcohols up to >99%. However, there is no effect of the match-mismatch pair of sulfinamide diastereomers on the outcome of the chiral induction of the product phenethyl alcohols. It was conclusively proved that chirality at the sulfur center is mandatory for obtaining good enantioselectivity in the reaction. (C) 2013 Elsevier Ltd. All rights reserved.
• Enantioselective addition of diethylzinc to aryl aldehydes catalyzed by 1,2,3,4-tetrahydroisoquinoline β-amino alcohol
  作者：Geng Xu、Zhan Zhu Liu

  DOI：10.1016/j.cclet.2009.11.046

  日期：2010.3

  Abstract A highly effective, new chiral 1,2,3,4-tetrahydroisoquinoline catalyst 1 for the diethylzinc addition to aryl aldehydes has been investigated. Using 10 mol% of this chiral catalyst, secondary alcohols can be obtained in up to 87% yield and 99.5% ee under mild conditions.

  摘要研究了一种高效的新型手性1,2,3,4-四氢异喹啉催化剂1，用于将二乙基锌加成芳基醛。使用10 mol％的这种手性催化剂，在温和条件下，可以以高达87％的收率和99.5％ee的速率获得仲醇。