(S)-3-(2-nitrophenoxy)-1,2-propanediol | 785817-21-2

• 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: (S)-3-(2-nitrophenoxy)-1,2-propanediol
• 英文别名: (S)-3-(2-nitrophenoxy)propane-1,2-diol；(2S)-3-(2-nitrophenoxy)propane-1,2-diol
• CAS: 785817-21-2
• 化学式: C₉H₁₁NO₅
• 分子量: 213.19
• InChiKey: VYYIKGCZHKHONW-ZETCQYMHSA-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：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  95.5
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-allyloxy-1-nitrobenzene 在 AD-mix-α 作用下， 以 水 、 叔丁醇 为溶剂， 以42%的产率得到
  参考文献：
  名称：

  A rare case of facial selectivity inversion for Sharpless asymmetric dihydroxylation in a series of structurally homogeneous substrates: synthesis of non-racemic 3-(nitrophenoxy)-propane-1,2-diols

  摘要：

  Asymmetric dihydroxylation of mono nitrophenyl allyl ethers leads to the corresponding non-racemic 3-(nitrophenoxy)-propane-1,2-diols 1a-c. As this takes place, regardless of the reagent used (AD-mix-alpha or AD-mix-beta), the configuration of the predominant enantiomer for the para- and meta-nitrosubstituted products is opposite to the configuration of the ortho-nitrophenyl derivative. A correlation between the melting points and vibrational spectra of the racemic and enantiopure diols 1a-c allowed us to establish that all of the chiral substances investigated formed stable racemic compounds in the solid phase. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2014.05.008

文献信息

• An Unusual (R)-Selective Epoxide Hydrolase with High Activity for Facile Preparation of Enantiopure Glycidyl Ethers
  作者：Jing Zhao、Yan-Yan Chu、Ai-Tao Li、Xin Ju、Xu-Dong Kong、Jiang Pan、Yun Tang、Jian-He Xu

  DOI：10.1002/adsc.201100031

  日期：2011.6

  ortho‐substituted phenyl glycidyl ethers and para‐nitrostyrene oxide. Worthy of note is that the substrate structure remarkably affected the enantioselectivities of the enzyme, as a reversed (S)‐enantiopreference was unexpectedly observed for the ortho‐nitrophenyl glycidyl ether. As a proof‐of‐concept, five enantiopure epoxides (>99% ee) were obtained in high yields, and a gram‐scale preparation of

  从巨大芽孢杆菌ECU1001中克隆了一种新的环氧水解酶（BMEH），该酶具有异常的（R）-对映体选择性和很高的活性。在对位取代的苯基缩水甘油醚和对硝基苯乙烯氧化物的生物拆分中，实现了最高的对映选择性（E > 200）。值得一提的是，底物结构显着影响了酶的对映选择性，因为人们意外地观察到邻硝基硝基苯缩水甘油醚的反向（S）-对映体选择性。作为概念验证，以高收率获得了五种对映纯环氧化合物（> 99％ee），并以克级制备了（S） -邻甲基苯基缩水甘油基醚，然后成功地在几个小时内完成，这表明BMEH为光学活性的环氧化物的高效制备有吸引力的生物催化剂。
• Chiral Nanoporous Metal–Metallosalen Frameworks for Hydrolytic Kinetic Resolution of Epoxides
  作者：Chengfeng Zhu、Guozan Yuan、Xu Chen、Zhiwei Yang、Yong Cui

  DOI：10.1021/ja302340b

  日期：2012.5.16

  recyclable heterogeneous catalyst for hydrolytic kinetic resolution (HKR) of racemic epoxides with up to 99.5% ee. The MOF structure brings Co(salen) units into a highly dense arrangement and close proximity that enhances bimetallic cooperative interactions, leading to improved catalytic activity and enantioselectivity in HKR compared with its homogeneous analogues, especially at low catalyst/substrate ratios

  手性纳米多孔金属有机框架是通过使用二羧基功能化的手性 Ni(salen) 和 Co(salen) 配体构建的。基于 Co(salen) 的框架被证明是一种高效且可回收的多相催化剂，用于外消旋环氧化物的水解动力学拆分 (HKR)，ee 高达 99.5%。MOF 结构使 Co(salen) 单元形成高度密集的排列和紧密接近，增强了双金属协同相互作用，与均相类似物相比，HKR 的催化活性和对映选择性提高，尤其是在低催化剂/底物比的情况​​下。
• Bacillus alcalophilus MTCC10234 catalyzed enantioselective kinetic resolution of aryl glycidyl ethers
  作者：Neeraj Bala、Swapandeep Singh Chimni、Harvinder Singh Saini、Bhupinder Singh Chadha

  DOI：10.1016/j.molcatb.2009.12.019

  日期：2010.5

  The phenyl glycidyl ether derivatives have been kinetically resolved with the growing cells of Bacillus alcalophilus MTCC10234 yielding (S)-epoxides with up to >99% ee and (R)-diols with up to 89% ee. The enantiomeric ratio (E) of up to 67 has been obtained for biohydrolysis process. The effect of different substituents of phenyl glycidyl ether on the biocatalytic efficiency of B. alcalophilus MTCC10234

  苯缩水甘油醚衍生物已经与嗜碱芽孢杆菌MTCC10234的生长细胞动力学分离，产生了（S）-环氧化合物，其ee含量高达> 99％，（R）-二醇的ee含量高达89％。对于生物水解过程，已获得高达67的对映体比率（E）。苯基缩水甘油基醚的不同取代基对嗜酸芽孢杆菌MTCC10234的生物催化效率的影响表明，甲基和氯取代的芳基缩水甘油基醚衍生物较为可取，而硝基衍生物的转化速度较慢。将含有在两个邻位均具有甲基的大体积芳基的2，6-二甲基苯基缩水甘油醚用N-甲基-N-二甲基苯甲酸酯进行拆分。E  = 39。
• A rare case of facial selectivity inversion for Sharpless asymmetric dihydroxylation in a series of structurally homogeneous substrates: synthesis of non-racemic 3-(nitrophenoxy)-propane-1,2-diols
  作者：Zemfira A. Bredikhina、Alexey V. Kurenkov、Olga A. Antonovich、Alexander V. Pashagin、Alexander A. Bredikhin

  DOI：10.1016/j.tetasy.2014.05.008

  日期：2014.7

  Asymmetric dihydroxylation of mono nitrophenyl allyl ethers leads to the corresponding non-racemic 3-(nitrophenoxy)-propane-1,2-diols 1a-c. As this takes place, regardless of the reagent used (AD-mix-alpha or AD-mix-beta), the configuration of the predominant enantiomer for the para- and meta-nitrosubstituted products is opposite to the configuration of the ortho-nitrophenyl derivative. A correlation between the melting points and vibrational spectra of the racemic and enantiopure diols 1a-c allowed us to establish that all of the chiral substances investigated formed stable racemic compounds in the solid phase. (C) 2014 Elsevier Ltd. All rights reserved.