(S)-1-(2-nitrophenyl)but-3-en-1-ol | 942066-78-6

• 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)-1-(2-nitrophenyl)but-3-en-1-ol
• 英文别名: (S)-1-(2-nitrophenyl)-3-buten-1-ol；(1S)-1-(2-nitrophenyl)but-3-en-1-ol
• CAS: 942066-78-6
• 化学式: C₁₀H₁₁NO₃
• 分子量: 193.202
• InChiKey: LPHRMSHWMNZFQZ-JTQLQIEISA-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 、 (S)-1-acetyl-N-tosylpyrrolidine-2-carboxamide 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以92%的产率得到(S)-1-(2-nitrophenyl)but-3-en-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。
• 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。
• Chiral phosphine oxide aziridinyl phosphonate as a Lewis base catalyst for enantioselective allylsilane addition to aldehydes
  作者：Özdemir Dogan、Adnan Bulut、M. Ali Tecimer

  DOI：10.1016/j.tetasy.2015.07.002

  日期：2015.9

  A series of chiral Lewis bases, phosphine oxide ferrocenyl aziridinyl methanol 1-4, phosphinyl aziridinyl phosphonates 5 and 6, and phosphine oxide aziridinyl phosphonates 7 and 8 were screened for allylsilane additions to aldehydes. Among the Lewis bases, 8 was found to catalyze the reaction by forming the product in up to 94% yield and with 77% ee. (C) 2015 Elsevier Ltd. All rights reserved.
• New chiral imino- and amino-sulfoxides as activators of allyl trichlorosilane in the asymmetric allylation of aldehydes
  作者：Vincenzo De Sio、Maria Rosaria Acocella、Rosaria Villano、Arrigo Scettri

  DOI：10.1016/j.tetasy.2010.04.015

  日期：2010.6

  Chiral 2-methylsulfinyl benzaldehyde proved to be a valuable starting material for a convenient approach towards a variety of imino- and amino-sulfoxides. The catalytic properties of these new ligands, as potential activators of allyl trichlorosilane, have been exploited in new catalytic procedures for the synthesis of enantioenriched homoallylic alcohols. (C) 2010 Elsevier Ltd. All rights reserved.