2-(2-nitro-1-(thioan-2-yl)ethyl)cyclohexanone

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: 2-(2-nitro-1-(thioan-2-yl)ethyl)cyclohexanone
• 英文别名: 2-(2-nitro-1-(thiophen-2-yl)ethyl)cyclohexan-1-one；2-(2-nitro-1-(thiophen-2-yl)ethyl)cyclohexanone；2-(2-Nitro-1-thiophen-2-ylethyl)cyclohexan-1-one；2-(2-nitro-1-thiophen-2-ylethyl)cyclohexan-1-one
• 化学式: C₁₂H₁₅NO₃S
• 分子量: 253.322
• InChiKey: IXTLLOSYBIWABX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  91.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-硝基乙烯基噻吩 、 环己酮 在 lipozyme TLIM 作用下， 以 水 、 二甲基亚砜 为溶剂， 反应 168.0h， 以73%的产率得到2-(2-nitro-1-(thioan-2-yl)ethyl)cyclohexanone
  参考文献：
  名称：

  The lipase-catalyzed asymmetric C–C Michael addition

  摘要：

  The example of enzyme-catalyzed asymmetric C-C Michael addition was observed using Lipozyme TLIM (immobilized lipase from Thermomyces lanuginosus) in organic medium in the presence of water. This biocatalysis is applicable to the Michael additions of a wide range of 1,3-dicarbonyl compounds and cyclohexanone to aromatic and heteroaromatic nitroolefins and cyclohexenone. The enantioselectivities up to 83% ee and yields up to 90% were achieved. The enzyme can be reused for three cycles. (C) 2010 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcatb.2010.11.011

文献信息

• Novel thiourea-amine bifunctional catalysts for asymmetric conjugate addition of ketones/aldehydes to nitroalkenes: rational structural combination for high catalytic efficiency
  作者：Jia-Rong Chen、Yi-Ju Cao、You-Quan Zou、Fen Tan、Liang Fu、Xiao-Yu Zhu、Wen-Jing Xiao

  DOI：10.1039/b925962g

  日期：——

  A series of thiourea-amine bifunctional catalysts have been developed by a rational combination of prolines with cinchona alkaloids, which are connected by a thiourea motif. The catalyst 3a, prepared from L-proline and cinchonidine, was found to be a highly efficient catalyst for the conjugate addition of ketones/aldehydes to a wide range of nitroalkenes (up to 98/2 dr and 96% ee). The privileged cinchonidine

  一系列 硫脲-胺双功能催化剂是通过脯氨酸与金鸡纳生物碱的合理组合而开发的，金鸡纳生物碱通过硫脲基序连接。催化剂3a由大号脯氨酸 和 辛可尼定被发现是一种高效的催化剂，用于将酮/醛共轭加成到各种各样的硝基烯烃中（高达98/2 dr和96％ee）。特权的辛可尼定骨架和硫脲基序对于反应活性和对映选择性是必不可少的。
• Novel bifunctional chiral squaramide-amine catalysts for highly enantioselective addition of mono and diketones to nitroalkenes
  作者：Ze Dong、Xiaoqing Jin、Pengcheng Wang、Chang Min、Jin Zhang、Zhe Chen、Hai-Bing Zhou、Chune Dong

  DOI：10.3998/ark.5550190.0012.927

  日期：——

  Novel bifunctional chiral squaramide–amine organocatalysts have been developed by rational combination of pyrrolidine and a cinchona alkaloid. The catalysts promoted the enantioselective Michael addition of both mono- and diketones to a broad range of nitroalkenes providing the corresponding products in moderate to high yields with excellent enantioselectivities and diastereoselectivities (up to 96%

  通过吡咯烷和金鸡纳生物碱的合理组合开发了新型双功能手性方酸酰胺-胺有机催化剂。该催化剂促进了单酮和二酮对广泛范围的硝基烯烃的对映选择性迈克尔加成，以中等至高产率提供相应的产物，具有优异的对映选择性和非对映选择性（产率高达 96%，96% ee，98:2 dr）。条件温和。这些结果表明，将两个手性特权骨架、吡咯烷和辛可宁与方酸酰胺连接器组装在一起是实现更广泛底物范围、高反应效率和对映选择性的有用策略。嵌入催化剂的两个主链之间手性的匹配对于提高对映选择性也很关键。
• Asymmetric Direct Michael Reactions of Cyclohexanone with Aromatic Nitroolefins in Water Catalyzed by Novel Axially Unfixed Biaryl-Based Bifunctional Organocatalysts
  作者：Hong-Wu Zhao、Zhao Yang、Yuan-Yuan Yue、Hai-Long Li、Xiu-Qing Song、Zhi-Hui Sheng、Wei Meng、Xiao-Yu Guo

  DOI：10.1055/s-0033-1340289

  日期：——

  new family of axially unfixed biaryl-based water-compatible bifuctional organocatalysts were designed and synthesized for the asymmetric direct Michael reaction of cyclohexanone with various nitroolefins in water. One of the organocatalysts incorporates pyrrolidine and arylsulfonamide motifs as active organocatalytic sites, and axially unfixed biaryl as a skeleton; with this organocatalyst, the direct

  设计并合成了一类新的轴向未固定联芳基水相容双功能有机催化剂，用于环己酮与水中各种硝基烯烃的不对称直接迈克尔反应。其中一种有机催化剂包含吡咯烷和芳基磺酰胺基序作为活性有机催化位点，以及轴向未固定的联芳基作为骨架；使用这种有机催化剂，直接迈克尔反应很容易进行，以高产率（高达 99% 的产率）提供所需的迈克尔加合物，并具有高水平的立体控制（高达 >99:1 dr 和 94% ee）。
• Pyrrolidine-diaminomethylenemalononitrile organocatalyst for Michael additions of carbonyl compounds to nitroalkenes under solvent-free conditions
  作者：Kosuke Nakashima、Shin-ichi Hirashima、Masahiro Kawada、Yuji Koseki、Norihiro Tada、Akichika Itoh、Tsuyoshi Miura

  DOI：10.1016/j.tetlet.2014.03.042

  日期：2014.4

  The novel pyrrolidine-diaminomethylenemalononitrile organocatalyst 7 promotes the asymmetric conjugate addition of a carbonyl compound to a nitroalkene to afford the corresponding adduct in high yield with up to 99% ee, under solvent-free conditions.

  新型的吡咯烷-二氨基亚甲基丙二腈有机催化剂7促进了羰基化合物向硝基烯烃的不对称共轭加成，从而在无溶剂条件下以高达99％ee的高收率提供了相应的加合物。
• Organocatalytic asymmetric Michael addition of aldehydes and ketones to nitroalkenes catalyzed by adamantoyl <scp>l</scp>-prolinamide
  作者：Yongchao Wang、Dong Li、Jun Lin、Kun Wei

  DOI：10.1039/c4ra11214h

  日期：——

  series of adamantoyl L-prolinamides have been synthesized. These compounds have been found to be highly efficient organocatalysts for the Michael addition of aldehydes and ketones to nitroalkenes. Under the optimized reaction conditions, the corresponding Michael adducts were obtained in good yields (up to 95%), excellent enantioselectivities (up to 99% ee) and moderate diastereoselectivities.

  已经合成了一系列的金刚烷基L-脯氨酰胺。已经发现这些化合物是用于将醛和酮迈克尔加成至硝基烯烃的高效有机催化剂。在优化的反应条件下，以高收率（最高95％），优异的对映选择性（最高99％ee）和中等非对映选择性获得了相应的迈克尔加合物。