1-(2-methoxy-phenyl)-2-nitro-propan-1-ol | 858811-30-0

• 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-(2-methoxy-phenyl)-2-nitro-propan-1-ol
• 英文别名: 1-(2-Methoxyphenyl)-2-nitropropan-1-ol
• CAS: 858811-30-0
• 化学式: C₁₀H₁₃NO₄
• 分子量: 211.218
• InChiKey: JTQOMHDMLSERRE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  75.3
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(2-methoxy-phenyl)-2-nitro-propan-1-ol 在 硫酸 、 苯甲醚 作用下， 生成 1-(2-methoxy-phenyl)-1-(4-methoxy-phenyl)-2-nitro-propane
  参考文献：
  名称：

  Synthesis of 1, 1-Bis(Alkoxyaryl)-2-Nitroalkanes for Insecticidal Evaluation

  摘要：

  DOI：

  10.1021/jo50004a012
• 作为产物：
  描述：

  邻甲氧基苯甲醛 在 sodium hydrogensulfite 作用下， 生成 1-(2-methoxy-phenyl)-2-nitro-propan-1-ol
  参考文献：
  名称：

  Synthesis of 1, 1-Bis(Alkoxyaryl)-2-Nitroalkanes for Insecticidal Evaluation

  摘要：

  DOI：

  10.1021/jo50004a012

文献信息

• Urea/Transition-Metal Cooperative Catalyst for anti-Selective Asymmetric Nitroaldol Reactions
  作者：Kai Lang、Jongwoo Park、Sukwon Hong

  DOI：10.1002/anie.201107785

  日期：2012.2.13

  A cooperative catalyst that features urea H‐bonding and a cobalt center was developed for anti‐selective asymmetric Henry reactions (see scheme). The H‐bonds of urea play a crucial role in the improvement in yield (from 30 % to 84 %), enantioselectivity (from 78 % to 96 %), and anti diastereoselectivity (from 3:1 to 48:1). A short synthesis of (1R,2S)‐methoxamine hydrochloride was also accomplished

  开发了一种具有尿素氢键和钴中心特征的协同催化剂，用于抗选择性不对称亨利反应（参见方案）。尿素的H键在提高收率（从30％到84％），对映选择性（从78％到96％）和抗非对映选择性（从3：1到48：1）方面起着至关重要的作用。用该催化剂还可以完成（1 R，2 S）-甲氧胺盐酸盐的简短合成。
• A Highly<i>anti</i>-Selective Asymmetric Henry Reaction Catalyzed by a Chiral Copper Complex: Applications to the Syntheses of (+)-Spisulosine and a Pyrroloisoquinoline Derivative
  作者：Kun Xu、Guoyin Lai、Zhenggen Zha、Susu Pan、Huanwen Chen、Zhiyong Wang

  DOI：10.1002/chem.201201775

  日期：2012.9.24

  A highly anti‐selective asymmetric Henry reaction has been developed, affording synthetically versatile β‐nitroalcohols in a predominately anti‐selective manner (mostly above 15:1) and excellent ee values (mostly above 95 %). Moreover, the anti‐selective Henry reaction was carried out in the presence of water for the first time with up to 99 % ee. The catalytic mechanism was proposed based on the detection

  已经开发出了一种高度抗选择性的不对称亨利反应，以一种主要是抗选择性的方式（大多数在15：1以上）和出色的ee值（大多数在95％以上）提供了合成通用的β-硝基醇。此外，抗选择性亨利反应是在水的存在下首次以高达99％  ee的条件进行的。基于萃取电喷雾电离质谱（EESI-MS）对中间体的检测，提出了催化机理。此外，抗加合物已成功转化为具有生化重要性的（+）-螺旋甜菜碱和吡咯并异喹啉衍生物。
• A Highly Diastereo- and Enantioselective Copper(I)-Catalyzed Henry Reaction Using a Bis(sulfonamide)−Diamine Ligand
  作者：Wei Jin、Xincheng Li、Boshun Wan

  DOI：10.1021/jo101932a

  日期：2011.1.21

  bis(sulfonamide)−diamine (BSDA) ligands were synthesized from commercially available chiral α-amino alcohols and diamines. The chiral BSDA ligand 3a, coordinated with Cu(I), catalyzes the enantioselective Henry reaction with excellent enantioselectivity (up to 99%). Moreover, with the assistance of pyridine, a CuBr−3a system promotes the diastereoselective Henry reaction with various aldehyde substrates

  从市售的手性α-氨基醇和二胺合成了一系列的双（磺酰胺）-二胺（BSDA）配体。与Cu（I）配位的手性BSDA配体3a以优异的对映选择性（高达99％）催化对映选择性亨利反应。此外，借助吡啶，CuBr- 3a系统可促进与各种醛底物的非对映选择性亨利反应，并以高达99％的收率和32.3：1的顺/反选择性提供相应的顺选择性加合物。顺式加合物的对映体过量为97％。
• A Highly syn-Selective Nitroaldol Reaction Catalyzed by CuII-Bisimidazoline
  作者：Liang Cheng、Jiaxing Dong、Jingsong You、Ge Gao、Jingbo Lan

  DOI：10.1002/chem.201000650

  日期：——

  Catalyzing Henry: Chiral bisimidazoline 1–Cu(OTf)2, in the presence of N‐methylmorpholine as a base, was discovered to efficiently catalyze the nitroaldol reaction in a highly syn‐ and enantioselective manner for a broad range of aldehydes, including aromatic, heteroaromatic, α,β‐unsaturated, and aliphatic aldehydes (see scheme).

  催化亨利（Henry）：发现在N-甲基吗啉为碱的存在下，手性双咪唑啉1 -Cu（OTf）2能以高合成和对映选择性的方式有效催化多种醛（包括芳族化合物）的硝基醛反应。杂芳族，α，β-不饱和和脂肪族醛（请参见方案）。
• Mn(OAc)2/Schiff base as a new efficient catalyst system for the Henry reaction of nitroalkanes with aldehydes
  作者：Guang Peng Zhou、Yong Hai Hui、Ning Ning Wan、Qiu Ju Liu、Zheng Feng Xie、Ji De Wang

  DOI：10.1016/j.cclet.2012.04.018

  日期：2012.6

  A series of novel Schiff bases bearing triazole structure were synthesized and characterized by IR and NMR. Mn(OAc)(2)/Schiff base efficiently catalyzed Henry reaction of nitroalkanes with aldehydes to produce the corresponding products of beta-nitroalcohols, under mild conditions with high yields (up to 99%). A reaction mechanism is proposed based on the experimental results. (C) 2012 Zheng Feng Xie. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.