(2S,3S)-2-(1-methylethyl)-4-nitro-3-phenylbutyraldehyde | 384354-78-3

• 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: (2S,3S)-2-(1-methylethyl)-4-nitro-3-phenylbutyraldehyde
• 英文别名: 2-isopropyl-4-nitro-3-phenyl butyraldehyde；(2S,3S)-2-isopropyl-3-phenyl-4-nitro-butyraldehyde；2-isopropyl-4-nitro-3-phenylbutanal；(2S,3S)-4-nitro-3-phenyl-2-propan-2-ylbutanal
• CAS: 384354-78-3
• 化学式: C₁₃H₁₇NO₃
• 分子量: 235.283
• InChiKey: XOGIFCAGQBTOQE-OLZOCXBDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  62.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  对甲苯磺酰氯 、 (2S,3S)-2-(1-methylethyl)-4-nitro-3-phenylbutyraldehyde 在 palladium dihydroxide 氢气 作用下， 生成 3-isopropyl-4-phenyl-1-(toluene-4-sulfonyl) pyrrolidine
  参考文献：
  名称：

  Catalytic Direct Asymmetric Michael Reactions:  Taming Naked Aldehyde Donors

  摘要：

  [GRAPHICS]Direct catalytic enantio- and diastereoselective Michael addition reactions of unmodified aldehydes to nitro olefins using (S)-2-(morpholinomethyl)-pyrrolidine as a catalyst are described. The reactions proceed in good yield (up to 96%) in a highly syn-selective manner (up to 98:2) with enantloselectivities approaching 80%. The resulting gamma -formyl nitro compounds are readily converted to chiral, nonracemic 3,4-disubstituted pyrrolidines.

  DOI：

  10.1021/ol0167006
• 作为产物：
  描述：

  反式硝基苯乙烯 、 异戊醛 在 (S)-(diphenyltrimethylsiloxymethyl)-pyrrolidine 作用下， 以 正己烷 为溶剂， 反应 46.0h， 生成 (2R,3S)-2-(1-methylethyl)-4-nitro-3-phenylbutanal 、 (2R,3R)-2-(1-methylethyl)-4-nitro-3-phenylbutyraldehyde 、 (2S,3S)-2-(1-methylethyl)-4-nitro-3-phenylbutyraldehyde
  参考文献：
  名称：

  二苯丙醇基甲硅烷基醚作为醛和硝基烯烃不对称迈克尔反应的有效有机催化剂。

  摘要：

  DOI：

  10.1002/anie.200500599

文献信息

• Readily Accessible 9-epi-amino Cinchona Alkaloid Derivatives Promote Efficient, Highly Enantioselective Additions of Aldehydes and Ketones to Nitroolefins
  作者：Séamus H. McCooey、Stephen J. Connon

  DOI：10.1021/ol0628006

  日期：2007.2.1

  from commercially available starting materials, have been shown to promote highly enantio- and diastereoselective Michael-type addition reactions between enolizable carbonyl compounds and nitroalkenes of broad scope. The influence of both the absolute and relative stereochemistry at C-9 on catalyst performance has also been assessed. [reaction: see text].

  通过一锅法可从市售原料中获得的简单金鸡纳生物碱衍生物已显示出可促进可烯丙基的羰基化合物与广泛范围的硝基烯烃之间的高度对映和非对映选择性迈克尔型加成反应。还评估了C-9处绝对和相对立体化学对催化剂性能的影响。[反应：请参见文字]。
• Efficient access to enantiomerically pure rigid diamines
  作者：Loı̈c Planas、Joëlle Pérard-Viret、Jacques Royer

  DOI：10.1016/j.tetasy.2004.06.011

  日期：2004.8

  Asymmetric spiro cyclization of a pyrrolidine derivative was used as a key step for constructing novel rigid diamines. A selected example has proved its utility as a chiral nonmetallic catalyst in a Michael reaction.

  吡咯烷衍生物的不对称螺环化被用作构建新型刚性二胺的关键步骤。一个选定的实例证明了其在迈克尔反应中作为手性非金属催化剂的用途。
• 3,3‘-Bimorpholine Derivatives as a New Class of Organocatalysts for Asymmetric Michael Addition
  作者：Sarah Mossé、Marju Laars、Kadri Kriis、Tõnis Kanger、Alexandre Alexakis

  DOI：10.1021/ol0607490

  日期：2006.6.1

  New N-alkyl-3,3'-bimorpholine derivatives (iPBM) were revealed to be efficient organocatalysts for the asymmetric direct Michael addition of aldehydes to nitroolefins and a vinyl sulfone. In these transformations using iPBM, 1,4-adducts were afforded in high yields, with good to high levels of diastereo- and enantioselectivity. The stereochemical outcome of the reaction could be explained by an acyclic

  揭示了新的N-烷基-3,3'-双吗啉衍生物（iPBM）是将醛不对称直接迈克尔加成至硝基烯烃和乙烯基砜的有效有机催化剂。在使用iPBM进行的这些转化中，以高收率提供了良好的非对映选择性和对映选择性的1,4-加合物。反应的立体化学结果可以用无环向斜模型解释。[反应：看文字]
• Remarkable Effect of <i>tert</i> ‐Amine Additives in the Asymmetric Direct Michael Reaction of Ketones with β‐Arylnitroethenes Catalyzed by an <i>L</i> ‐Hydroxyproline‐Based Amino Tf‐Amide Organocatalyst
  作者：Hanbin Lu、Jiamin Lv、Canhua Zhou、Mi Zhou、Yanxiong Fang、Jinxiang Dong、Terumasa Kato、Yan Liu、Keiji Maruoka

  DOI：10.1002/ejoc.202100090

  日期：2021.3.26

  A catalytic asymmetric direct Michael reaction of ketones with trans‐β‐arylnitroethenes has been developed by using optically pure L‐hydroxyproline‐based secondary‐amino aromatic Tf‐amide organocatalyst. The effect of diethylmethylamine base additive is of crucial importance to accelerate the reaction and also to achieve high enantioselectivity.

  通过使用光学纯的基于L-羟基脯氨酸的仲氨基芳族Tf-酰胺有机催化剂，已开发了酮与反式-β-芳基硝基乙烯的催化不对称直接迈克尔反应。二乙基甲胺碱添加剂的作用对于加快反应并实现高对映选择性至关重要。
• Environmental modulation of chiral prolinamide catalysts for stereodivergent conjugate addition
  作者：Xiaowei Li、Yan Zhao

  DOI：10.1016/j.jcat.2022.01.003

  日期：2022.2

  Synthetic chiral catalysts generally rely on proximal functional groups or ligands for chiral induction. Enzymes often employ environmental chirality to achieve stereoselectivity. Environmentally controlled catalysis has benefits such as size and shape selectivity but is underexplored by chemists. We here report molecularly imprinted nanoparticles (MINPs) that utilized their environmental chirality to either

  合成手性催化剂通常依靠近端官能团或配体进行手性诱导。酶通常利用环境手性来实现立体选择性。环境控制的催化具有尺寸和形状选择性等优点，但化学家尚未充分探索。我们在此报告了分子印迹纳米粒子 (MINPs)，该纳米粒子利用其环境手性来增强或逆转手性脯氨酰胺辅因子的内在选择性。后一种能力允许催化剂产生在醛与硝基烯烃的共轭加成中不受欢迎的产物。催化在室温下发生在水中，并以优异的收率（高达 94%）和 ee（在大多数情况下>90%）提供 γ-硝基醛。高达 25:1同步/反通过结合催化剂衍生的选择性和环境启用的选择性，实现了1:6的顺/反比。MINP 的高对映选择性也使外消旋催化剂能够进行不对称催化，共轭加成的 ee 高达 80%。