(1'S,3R)-3-(1'-nitroethyl)cyclohexanone | 804531-67-7

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 英文名称: (1'S,3R)-3-(1'-nitroethyl)cyclohexanone
• 英文别名: (3R)-3-[(1S)-1-nitroethyl]cyclohexan-1-one
• CAS: 804531-67-7
• 化学式: C₈H₁₃NO₃
• 分子量: 171.196
• InChiKey: UNJFNXOQUDPIMG-NKWVEPMBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  62.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  trimethyl-[(3R)-3-[(1S)-1-nitroethyl]cyclohexen-1-yl]oxysilane 在 盐酸 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以100%的产率得到(1'S,3R)-3-(1'-nitroethyl)cyclohexanone
  参考文献：
  名称：

  手性四氟化铵季铵盐催化的环状α，β-不饱和酮的不饱和迈克尔硅酸酯的不对称迈克尔加成反应：旋光性γ-硝基酮的烯醇甲硅烷基醚的分离和选择性官能化

  摘要：

  通过将N-螺碳C 2对称的手性四氟化季铵盐1作为有效催化剂，实现了对环α，β-不饱和酮的高对映选择性迈克尔加成反应，为光学上制备烯醇式甲硅烷基醚提供了一条新途径。活性γ-硝基酮。通过光学活性的烯醇甲硅烷基醚的非对映选择性衍生化为具有三个连续的立体化学定义的立体中心的相应的α-取代的环酮，已经证明了该转化的合成效用。

  DOI：

  10.1016/j.tetlet.2005.10.154

文献信息

• An efficient, asymmetric organocatalyst-mediated conjugate addition of nitroalkanes to unsaturated cyclic and acyclic ketones
  作者：Claire E. T. Mitchell、Stacey E. Brenner、Jorge García-Fortanet、Steven V. Ley

  DOI：10.1039/b601877g

  日期：——

  5-Pyrrolidin-2-yltetrazole is a versatile organocatalyst for the asymmetric conjugate addition of nitroalkanes to enones. Using this catalyst, this transformation requires short reaction times, tolerates a broad substrate scope, and possibly proceeds via generation of an iminium species.

  5-吡咯烷-2-基四唑是一种通用的有机催化剂，用于将硝基烷烃不对称地加成成烯酮。使用这种催化剂，这种转化需要较短的反应时间，可以耐受广泛的底物范围，并且可能通过生成亚胺鎓类物质进行。
• Asymmetric conjugate addition of nitroalkanes to enones with a chiral α-aminophosphonate catalyst
  作者：Marcus Malmgren、Johan Granander、Mohamed Amedjkouh

  DOI：10.1016/j.tetasy.2008.07.007

  日期：2008.8

  Chiral diethyl (2R)-tetrahydropyrro-2-ylphosphonate is an effective catalyst for the Michael addition of nitroalkanes to alpha,beta-unsaturated ketones. This Study revealed that the hydrate salt of this alpha-aminophosphonate was found to be a better catalytic species. Moderate to high enantioselectivities were achieved in reactions that tolerate various nitroalkanes and enones in the presence of low loading of both catalyst ( 10 mol %) and bulk base (25 mol %). (C) 2008 Published by Elsevier Ltd.
• 4-trans-Amino-proline based di- and tetrapeptides as organic catalysts for asymmetric C–C bond formation reactions
  作者：Svetlana B. Tsogoeva、Sunil B. Jagtap、Zoya A. Ardemasova

  DOI：10.1016/j.tetasy.2006.03.012

  日期：2006.3

  4-trans-Amino-proline based di- and tetrapeptides have been successfully applied as chiral organocatalysts in the enantioselective conjugate addition of nitroalkanes to cyclic enones and the direct aldol reaction. Two 4-trans-amino-proline residues were shown to be sufficient enough to catalyze the conjugate addition reactions with up to 88% ee and up to 100% yield. It has been demonstrated that 4-trans-amino-proline based di- and tetrapeptides are significantly more active than L-proline (at 30 mol %) and can catalyze the direct aldol reaction with good yield and enantioselectivity within 3 h and at lower catalyst loading (5 mol %). (c) 2006 Elsevier Ltd. All rights reserved.
• Asymmetric Michael addition of silyl nitronates to cyclic α,β-unsaturated ketones catalyzed by chiral quaternary ammonium bifluorides: isolation and selective functionalization of enol silyl ethers of optically active γ-nitro ketones
  作者：Takashi Ooi、Kanae Doda、Saki Takada、Keiji Maruoka

  DOI：10.1016/j.tetlet.2005.10.154

  日期：2006.1

  Highly enantioselective Michael addition of silyl nitronates to cyclic α,β-unsaturated ketones has been accomplished by the utilization of N-spiro C2-symmetric chiral quaternary ammonium bifluoride 1 as an efficient catalyst, offering a new route to the enol silyl ethers of optically active γ-nitro ketones. The synthetic utility of this transformation has been demonstrated by the diastereoselective

  通过将N-螺碳C 2对称的手性四氟化季铵盐1作为有效催化剂，实现了对环α，β-不饱和酮的高对映选择性迈克尔加成反应，为光学上制备烯醇式甲硅烷基醚提供了一条新途径。活性γ-硝基酮。通过光学活性的烯醇甲硅烷基醚的非对映选择性衍生化为具有三个连续的立体化学定义的立体中心的相应的α-取代的环酮，已经证明了该转化的合成效用。