1-(2-bromophenyl)-2-nitropropan-1-ol | 862789-44-4

• 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-bromophenyl)-2-nitropropan-1-ol
• CAS: 862789-44-4
• 化学式: C₉H₁₀BrNO₃
• 分子量: 260.087
• InChiKey: TZQSGDSUBFFCBY-IMTBSYHQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.15
• 重原子数：
  14.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  63.37
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  硝基乙烷 、 邻溴苯甲醛 在 C₃₆H₄₆Cu₂N₂O₄ 、 4-甲氧基苯酚 作用下， 以 叔丁醇 为溶剂， 反应 123.0h， 以95%的产率得到
  参考文献：
  名称：

  氨基异冰片酚Schiff碱Cu2（SBAIB-d）2的铜配合物：直接催化不对称硝基吲哚（Henry）反应的高效催化剂

  摘要：

  为有效的直接催化不对称亨利反应，开发了一种新的氨基异冰片醇席夫碱双功能铜配合物Cu 2（SBAIB-d）2。一摩尔％的这种催化剂可产生高收率（高达99％ee）的预期亨利产物，并具有出色的对映选择性（高达98％ee）。本催化剂的实用性也扩展到了与硝基乙烷和1-硝基丙烷的亨利反应，从而以中等至高的收率（高达99％）提供了相应的产物，同时具有中等至高的对映体选择性的顺式（高达98％ee）和反（高达98％ee）非对映体。该催化体系的亮点是易于操作，耐空气和湿气，需要1摩尔％的易于合成的催化剂以及对多种底物都具有很高的对映选择性。

  DOI：

  10.1002/adsc.201200337

文献信息

• Nitroaldol-reaction of aldehydes in the presence of non-activated Mg:Al 2:1 hydrotalcite; a possible new mechanism for the formation of 2-aryl-1,3-dinitropropanes
  作者：Agnieszka Cwik、Aliz Fuchs、Zoltán Hell、Jean-Marc Clacens

  DOI：10.1016/j.tet.2005.02.055

  日期：2005.4

  Commercially available, non-activated 2:1 Mg:Al hydrotalcite catalyzes the nitroaldol reaction between a variety of aromatic and aliphatic aldehydes and simple nitroalkanes such as nitromethane and nitroethane. A new mechanism is proposed for the formation of the 1,3-dinitropropanes. The threo/erythro diastereoselectivity of the nitroethane-adducts was determined by 1H NMR spectroscopy and was found

  市售的未活化2：1 Mg：Al水滑石可催化各种芳香族和脂肪族醛与简单的硝基烷烃（如硝基甲烷和硝基乙烷）之间的硝基醛反应。提出了一种新的机理来形成1，3-二硝基丙烷。的苏/赤的硝基乙烷加合物的非对映选择性，通过测定1个H NMR光谱，发现其范围从50:50至70:30。芳族醛的取代基影响异构体比率。
• Guanidine Compound and Asymmetric Reaction Using the Same
  申请人：Terada Masahiro

  公开号：US20080154036A1

  公开（公告）日：2008-06-26

  A guanidine compound having a biaryl skeleton represented by the following formula (1), which is useful as a catalyst for various asymmetric reactions. (wherein R 1 , R 2 and R 3 each independently represent a hydrogen atom, a hydrocarbon group optionally having substituent(s), or a heterocyclic group optionally having substituent(s); R 4 to R 15 each independently represent a hydrogen atom, a hydrocarbon group optionally having substituent(s), a heterocyclic group optionally having substituent(s), a hydroxy group, an alkoxy group optionally having substituent(s), an aryloxy group optionally having substituent(s), an acyl group, an alkoxycarbonyl group optionally having substituent(s), an aryloxycarbonyl group optionally having substituent(s), a carbamoyl group optionally having substituent(s), an alkylthiocarbonyl group optionally having substituent(s), an arylthiocarbonyl group optionally having substituent(s), a carboxyl group, an alkylthio group optionally having substituent(s), an arylthio group optionally having substituent(s), an amino group or a substituted amino group, or a substituted silyl group; or in any combination of R 1 to R 15 , these substituents may be taken together to form a ring; and X 1 to X 8 represent a hydrogen atom or a nitrogen atom, provided that, in the case of a nitrogen atom, there is no substituent on X 1 to X 8 .

  具有以下式（1）表示的双芳基骨架的胍啉化合物，可用作各种不对称反应的催化剂。（其中，R1、R2和R3分别独立表示氢原子，可选地具有取代基的烃基或可选地具有取代基的杂环基；R4到R15独立地表示氢原子，可选地具有取代基的烃基，可选地具有取代基的杂环基，羟基，可选地具有取代基的烷氧基，可选地具有取代基的芳基氧基，酰基，可选地具有取代基的烷氧羰基，可选地具有取代基的芳基氧羰基，可选地具有取代基的氨基甲酰基，可选地具有取代基的硫代氨基甲酰基，可选地具有取代基的硫代芳基氨基甲酰基，羧基，可选地具有取代基的烷硫基，可选地具有取代基的芳基硫基，氨基或取代氨基，或取代硅基；或在R1到R15的任何组合中，这些取代基可结合在一起形成环；X1到X8表示氢原子或氮原子，前提是，在氮原子的情况下，X1到X8上没有取代基。
• Catalytic Asymmetric Henry Reaction of Nitroalkanes and Aldehydes Catalyzed by a Chiral <i>N</i>,<i>N</i>′<i>-</i>Dioxide/Cu(I) Complex
  作者：Hongjiang Mei、Xiao Xiao、Xiaohu Zhao、Bing Fang、Xiaohua Liu、Lili Lin、Xiaoming Feng

  DOI：10.1021/jo5027832

  日期：2015.2.20

  An easily available N,N′-dioxide/Cu(I) complex has been developed for the catalytic asymmetric nitroaldol (Henry) reaction of aldehydes with nitroethane. Under mild reaction conditions, a series of substituted aromatic, heteroaromatic and α,β-unsaturated aldehydes are transformed to the corresponding anti-β-nitroalcohols in good to excellent yields (up to 99%) with moderate to good dr (up to 16.7:1

  已开发出一种易于获得的N，N'-二氧化物/ Cu（I）络合物，用于醛与硝基乙烷的催化不对称硝基醛醇（Henry）反应。下温和的反应条件下，一系列的取代的芳族，杂芳族和α，β -不饱和醛转化为相应的抗-β-硝基醇以良好至优异的产率（高达99％）的中度至良好博士（高达1670： 1 anti / syn）和高ee值（高达97％）。除硝基乙烷外，还使用硝基甲烷和1-硝基丙烷作为亲核试剂，并获得了良好的对映选择性。
• Enantioselective Henry (nitroaldol) reaction catalyzed by axially chiral guanidines
  作者：Hitoshi Ube、Masahiro Terada

  DOI：10.1016/j.bmcl.2009.03.097

  日期：2009.7

  The enantioselective activation of nitroalkanes was attempted on the basis of the complexation between chiral guanidinium and nitronate through two hydrogen bonds. The proposed enantioselective activation was applied to the diastereo- and enantioselective Henry (nitroaldol) reaction of nitroalkanes with aldehydes using axially chiral guanidine bases as the catalyst. Optically active nitroaldol products

  在手性胍和亚硝酸盐通过两个氢键的络合的基础上，尝试了对硝基烷的对映选择性活化。使用轴向手性胍碱作为催化剂，将拟议的对映选择性活化作用应用于硝基烷烃与醛的非对映和对映选择性亨利（硝基醛醇）反应。在低温下以可接受的产率获得了旋光性硝基醛醇产物，其具有相当好的对映体和非对映体选择性。
• (S)-Pyrrolidine-Containing Chiral Manganese(III)–Salalen and –Salan Complexes as Catalysts for the Asymmetric Henry Reaction
  作者：Surendra Singh、Pramod Kumar、ManMohan Chauhan、Geeta Yadav

  DOI：10.1055/s-0035-1560595

  日期：——

  Chiral Mn(III)-salalen and -salan complexes derived from (S)-proline have been used as catalysts for the asymmetric Henry (nitro-aldol) reaction. We have also used this methodology for a variety of substrates to afford nitroaldol products in 40-94% yields with 25-92% ee.