3-(3-硝基苯氧基)-1,2-丙烷二醇 | 63991-99-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 3-(3-硝基苯氧基)-1,2-丙烷二醇
• 英文名称: rac-3-(3-nitrophenoxy)-1,2-propanediol
• 英文别名: (3-nitrophenoxy)propan-1,2-diol；3-(m-Nitrophenoxy)-1,2-propanediol；3-(3-nitrophenoxy)propane-1,2-diol
• CAS: 63991-99-1
• 化学式: C₉H₁₁NO₅
• 分子量: 213.19
• InChiKey: HJYXCTLKGAOVHQ-UHFFFAOYSA-N

物化性质

• 沸点：
  436.3±30.0 °C(Predicted)
• 密度：
  1.387±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 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

• 作为反应物：
  描述：

  3-(3-硝基苯氧基)-1,2-丙烷二醇 在 吡啶 、 4-二甲氨基吡啶 、 baker's yeast 、 草酰氯 、 sodium phosphate buffer 、 二甲基亚砜 、 三乙胺 、 蔗糖 作用下， 以 二氯甲烷 为溶剂， 反应 4.83h， 生成 (R)-3-(3-nitrophenoxy)-1,2-propanediol
  参考文献：
  名称：

  Baker's yeast mediated stereoselective biotransformation of 1-acetoxy-3-aryloxypropan-2-ones

  摘要：

  A series of 1-acetoxy-3-aryloxypropan-2-ones la-m were synthesized and subjected to biotransformation by baker's yeast yielding optically active monoacetates 5 or ent-5 and/or diols 4 of moderate to excellent enantiomeric purity. The dependence of the reduction/hydrolysis ratio and stereoselectivity on the size and substitution pattern of the aromatic moiety in the substrate is also discussed. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(97)00626-5
• 作为产物：
  描述：

  间硝基苯酚 、 3-氯-1,2-丙二醇 在 丙醇 、 sodium 作用下， 反应 24.0h， 以60%的产率得到3-(3-硝基苯氧基)-1,2-丙烷二醇
  参考文献：
  名称：

  Farsa, Oldrich; Kana, Jakub; Macku, Irena, Acta poloniae pharmaceutica, 2017, vol. 74, # 1, p. 127 - 135

  摘要：

  DOI：

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。
• 4-oxo-4,7-dihydrothieno[2,3-b]pyridine-5-carboxamides as antiviral agents
  申请人：Schnute Edward Mark

  公开号：US20050004161A1

  公开（公告）日：2005-01-06

  The invention provides a compound of formula I: wherein A, B, R 1 , R 2 , R 3 , and R 4 are as defined in the specification. The compounds of the present invention are useful for treating viral infections, in particular a herpesviral infection.

  该发明提供了化合物I的结构，其中A、B、R1、R2、R3和R4如规范中定义。本发明的化合物对治疗病毒感染，特别是单纯疱疹病毒感染，具有实用价值。
• A biocatalytic approach for regioselective monoacetylation of 3-aryloxy-1,2-propanediols by porcine pancreatic lipase
  作者：Vachan Singh Meena、U. C. Banerjee

  DOI：10.1007/s00706-011-0688-y

  日期：2012.6

  AbstractAmong the various lipases screened for the regioselective monoacetylation of 3-aryloxy-1,2-propanediols, porcine pancreatic lipase was found to afford a higher yield. The selectivity for the monoacetylation process was maximized by using different organic solvents and diisopropyl ether gave the highest conversion to monoacetylated product (ca. 98%). The optimized reaction afforded excellent

  摘要在为3-芳氧基-1，2-丙二醇的区域选择性单乙酰化而筛选的各种脂肪酶中，发现猪胰脂肪酶的产率更高。通过使用不同的有机溶剂，可以使单乙酰化过程的选择性最大化，二异丙醚转化为单乙酰化产物的转化率最高（约98％）。优化的反应提供了优异的单乙酰化产物收率，并且在原料中存在各种芳基取代基的情况下，在末端羟基处具有区域选择性。 图形概要
• 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.
• [EN] 2-PHENYLAMINO-4-(5-PYRAZOLYLAMINO)-PYRIMIDINE DERIVATIVES AS KINASE INHIBITORS, IN PARTICULAR, SRC KINASE INHIBITORS<br/>[FR] DERIVES DE 2-PHENYLAMINO-4-(5-PYRAZOLYLAMINO)-PYRIMIDINE EN TANT QU'INHIBITEURS DE LA KINASE, NOTAMMENT, DES INHIBITEURS DE LA KINASE SRC
  申请人：BAYER AG

  公开号：WO2003026665A1

  公开（公告）日：2003-04-03

  This application discloses and claims 5-substituted-2,4-diaminopyrimidines, (I) in which R1 represents C¿1-6? alkyl, C3-6 cycloalkyl, adamantyl, phenyl, or a 5-membered heteroaromatic containing a single heteroatom selected from N, O, and S. R?2¿ represents H, F, Cl, or C¿1-4? alkyl. R?3¿ represents H, halogen,O(C¿1-4alkyl), or C¿1-6?alkyl. R?4 represents halogen, NO2, C1-6 alkyl, NR?5R6¿, O(CH¿2?)1-4-CO2R?7¿, O(CH¿2?)1-4-C(O)NR?5R6, N(R5¿)C(O)CH¿2OR?8, OC(O)R9, C(O)NR5R6, CO2R7, CN, or O(C¿1-4?alkyl) optionally substituted by OH or phenoxy, pharmaceutical compositions containing them, a method of making them, and methods of using them for treatment of cancers.