(S)-1-[5-nitro-2-furyl]-3-buten-1-ol | 1151548-83-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃
• 英文名称: (S)-1-[5-nitro-2-furyl]-3-buten-1-ol
• 英文别名: (S)-(-)-1-(5-nitro-2-furyl)but-3-en-1-ol；(1S)-1-(5-nitrofuran-2-yl)but-3-en-1-ol
• CAS: 1151548-83-2
• 化学式: C₈H₉NO₄
• 分子量: 183.164
• InChiKey: QPTSRZDXSXPPRP-LURJTMIESA-N

物化性质

• 沸点：
  266.0±40.0 °C(predicted)
• 密度：
  1.278±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  79.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  5-硝基糠醛 、 丙烯基三氯硅烷 在 (R)-(+)-甲基对甲苯砜 、 四丁基碘化铵 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 以99%的产率得到(S)-1-[5-nitro-2-furyl]-3-buten-1-ol
  参考文献：
  名称：

  Chiral sulfoxides as activators of allyl trichlorosilanes in the stereoselective allylation of aldehydes

  摘要：

  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。

  DOI：

  10.1039/c002988b

文献信息

• Sulfoxides in the allylation of aldehydes in the presence of silicon tetrachloride and allyltributylstannane
  作者：Antonio Massa、Laura Capozzolo、Arrigo Scettri

  DOI：10.2478/s11532-010-0099-7

  日期：2010.12.1

  SiCl4 can be conveniently activated by catalytic amounts of dimethyl sulfoxide or other readily-available sulfoxides for the allylation of aromatic, hetero-aromatic and unsaturated aldehydes in the presence of allyltributyl stannane. Chiral aryl methyl sulfoxides have been used to develop asymmetric allylation methods, as well as probe the aldehyde substrate scope.

  SiCl 4 可以通过催化量的二甲基亚砜或其他容易获得的亚砜在烯丙基三丁基锡烷存在下方便地活化，用于芳族、杂芳族和不饱和醛的烯丙基化。手性芳基甲基亚砜已被用于开发不对称烯丙基化方法，以及探测醛底物范围。
• A catalytic asymmetric allylation of aldehydes with allyl trichlorosilane activated by a chiral tetradentate bis-sulfoxide
  作者：Antonio Massa、Maria Rosaria Acocella、Vincenzo De Sio、Rosaria Villano、Arrigo Scettri

  DOI：10.1016/j.tetasy.2009.01.023

  日期：2009.2

  Chiral homoallylic alcohols are easily accessible by asymmetric allylation of aldehydes with allyl trichlorosilane in the presence of catalytic amounts of a chiral tetradentate bis-sulfoxide, as organocatalyst, whose synthesis is reported.

  在有催化量的手性四齿双亚砜作为有机催化剂存在下，通过醛与烯丙基三氯硅烷的不对称烯丙基化反应，很容易获得手性均烯醇。
• 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。
• 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.
• 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。