(R)-1-(2-nitrophenyl)-3-buten-1-ol | 1260596-70-0

• 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: (R)-1-(2-nitrophenyl)-3-buten-1-ol
• 英文别名: (1R)-1-(2-nitrophenyl)but-3-en-1-ol
• CAS: 1260596-70-0
• 化学式: C₁₀H₁₁NO₃
• 分子量: 193.202
• InChiKey: LPHRMSHWMNZFQZ-SNVBAGLBSA-N

物化性质

• 沸点：
  340.0±27.0 °C(Predicted)
• 密度：
  1.204±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  66
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3-溴丙烯 、 邻硝基苯甲醛 在 tin 、 C₁₄H₁₇NO₅S 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以85%的产率得到(R)-1-(2-nitrophenyl)-3-buten-1-ol
  参考文献：
  名称：

  An efficient route for the allylation of arylaldehydes to give enantiopure homoallylic alcohols

  摘要：

  An efficient asymmetric synthesis of homoallylic alcohols is described by the allylation of carbonyl compounds using organocatalysts as chiral directors in the presence of tin metal. The effect of chiral environment is also studied on the allylation reactions. This method allows us to obtain two different enantiomers of homoallylic alcohol in the presence of the corresponding chiral compound. The protocol is applied to various aldehydes to obtain high yields and excellent enantioselectivities for the corresponding homoallylic alcohols. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2013.08.016

文献信息

• Chiral sulfoxides as activators of allyl trichlorosilanes in the stereoselective allylation of aldehydes
  作者：Vincenzo De Sio、Antonio Massa、Arrigo Scettri

  DOI：10.1039/c002988b

  日期：——

  Chiral aryl methyl sulfoxides proved to be efficient activators in the asymmetric allylation of aldehydes with allyl trichlorosilanes. High enantioselectivity was found in the case of electron-poor aldehydes. The high levels of diastereoselectivity and the detection of nonlinear effects have allowed the elucidation of some mechanistic aspects of the reaction.

  手性芳基甲基亚砜在不对称烯丙基化醛与烯丙基三氯硅烷反应中被证明是有效的催化剂。对于电子贫穷的醛，发现了高的对映选择性。高水平的差向选择性及非线性效应的检测使得反应的一些机理方面得以阐明。
• Bispalladacycle Catalyzed Nucleophilic Enantioselective Allylation of Aldehydes by Allylstannanes
  作者：Martin Heberle、Sarah Legendre、Nick Wannenmacher、Manuel Weber、Wolfgang Frey、René Peters

  DOI：10.1002/cctc.202200093

  日期：2022.5.6

  Bimetallic catalysis: The first palladium catalysts capable of controlling asymmetric nucleophilic allylations of aldehydes with allyltributyltin are reported. Unprecedented TONs for this reaction type were achieved (up to 620). The method is also tolerating electronically and sterically unfavorable substrates. A transmetallation occurs, favoring an η1-allyl coordination mode with the reported bispalladacycle

  双金属催化：报道了第一个能够控制醛与烯丙基三丁基锡的不对称亲核烯丙基化的钯催化剂。这种反应类型的 TON 达到了前所未有的水平（高达 620）。该方法还可以容忍电子和空间上不利的底物。发生金属转移，有利于 η 1 -烯丙基配位模式与报道的双钯环催化剂，而对于相应的单钯环催化剂，非生产性的 η 3 -配位占主导地位。
• Asymmetric Allylation of Aldehydes Catalyzed by Simple Dual Small Organic Molecules: L-Proline and L-Prolinol
  作者：Guo-hong Chen、Ling-yan Liu、Xiao-ning Wei、Wei-xing Chang、Jing Li

  DOI：10.1246/cl.2010.1013

  日期：2010.9.5

  A novel and simple methodology for the asymmetric allylation of aldehydes was reported. Double small organic molecules such as l-proline and l-prolinol were first employed for providing a chiral environment so as to afford chiral homoallylic alcohols in high yields and moderate enantioselectivities in our protocol.

  报道了一种新颖且简单的用于醛的不对称烯基化的方法。首次使用了双小有机分子如L-脯氨酸和L-脯氨醇，提供手性环境，从而在我们的方案中获得了高产率和中等对映选择性的手性同烯醇。
• Heteropoly Acid Supported on Silica Gel as Catalyst for the Asymmetric Transfer Allylation of Aromatic Aldehydes under Solvent-Free Conditions
  作者：Hiyoshizo Kotsuki、Shiori Nunokawa、Kazuya Oki、Keisuke Yamashita、Atsushi Okuyama、Tadaharu Ueda、Keiji Nakano、Yoshiyasu Ichikawa

  DOI：10.1055/s-0036-1588121

  日期：——

  A new convenient method for the asymmetric transfer allylation of aromatic aldehydes was developed. The reaction gave the best results using a chiral allyl donor molecule derived from (–)-menthone in the presence of heteropoly acids supported on silica gel under solvent-free conditions, and the desired homoallylic alcohol derivatives were obtained in good yields with good to high enantioselectivity

  开发了一种新的方便的芳香醛不对称转移烯丙基化方法。在无溶剂条件下，在硅胶负载的杂多酸存在下，使用衍生自 (-)-薄荷酮的手性烯丙基供体分子的反应得到了最好的结果，并且以良好的收率获得了所需的高烯丙醇衍生物。对映选择性。
• Hollow organic polymeric nano-bowls-supported BINOL-derived chiral phosphoric acid: enhanced catalytic performances in the enantioselective allylation of aromatic aldehydes
  作者：Zhengwei Yan、Guangxin Xie、Jianing Zhang、Xuebing Ma

  DOI：10.1016/j.mcat.2018.12.014

  日期：2019.2

  To improve the catalytic efficiency of expensive and versatile 1, 1′-binaphthol-derived chiral phosphoric acid with 2, 4, 6-tris(isopropyl)phenyl substituents and mass transfer of reactants in heterogeneous catalysis, a hollow organic polymeric nano-bowl was used as an effective catalyst support to anchor chiral phosphoric acid through the copolymerization of vinylated 1, 1′-binaphthol with 2, 4,

  为提高昂贵，通用的1，2,4-，6-三（异丙基）苯基取代的1,1'-联萘酚衍生的手性磷酸的催化效率以及在非均相催化中反应物的传质，提出了一种中空的有机聚合物纳米碗通过在聚苯乙烯纳米球核表面上将苯乙烯化的1、2'，6，三（异丙基）苯基取代的乙烯基化的1、1'-联萘酚与苯乙烯共聚，用作有效的催化剂载体来固定手性磷酸，并通过DMF蚀刻聚苯乙烯纳米球然后通过POCl 3磷酸化。从对4-氯苯甲醛与烯丙基硼酸频哪醇酯的不对称烯丙基硼化反应中反应物的反应动力学的比较动力学研究来看，所制备的空心有机聚合物纳米碗负载手性磷酸的催化速率比以往报道的相似催化剂高。在整个过程中具有恒定的催化速率（0.031 mol L -1  h -1）。芳香族醛类化合物的扩展范围进一步证明，中空有机聚合物纳米碗负载的手性磷酸由于其薄的壳厚度（18 nm）和中空结构而具有更高的活性和对映选择性。由于第六次重复使用的催化剂中恒定的