(R*)-2-((R*)-1-(benzo[d][1,3]dioxol-5-yl)-2-nitroethyl)-cyclohexan-1-one | 56579-87-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: (R*)-2-((R*)-1-(benzo[d][1,3]dioxol-5-yl)-2-nitroethyl)-cyclohexan-1-one
• 英文别名: 2-(1-(benzo[d] [1,3]dioxol-5-yl)-2-nitroethyl)cyclohexanone；2-[1-(1,3-Benzodioxol-5-yl)-2-nitroethyl]cyclohexanone；2-[1-(1,3-benzodioxol-5-yl)-2-nitroethyl]cyclohexan-1-one
• CAS: 56579-87-4
• 化学式: C₁₅H₁₇NO₅
• 分子量: 291.304
• InChiKey: OJSFQMPLWDVTCD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  81.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  1-吗啉基-1-环己烯 、 5-((E)-2-nitroethenyl)-1,3-benzodioxole 以 乙醚 为溶剂， 以91%的产率得到(R*)-2-((R*)-1-(benzo[d][1,3]dioxol-5-yl)-2-nitroethyl)-cyclohexan-1-one
  参考文献：
  名称：

  （E）-烯胺与（E）-硝基烯烃的非对映选择性迈克尔-加成合成开链2,3-二取代的4-硝基酮。前手性中心之间的C，C键形成过程的拓扑规则。初步沟通

  摘要：

  脂族，脂环族和芳基取代的硝基烯烃和烯胺的迈克尔加成导致γ-硝基酮3具有良好的化学性质和优异的（> 90％）非对映体产率（参见表1）。

  DOI：

  10.1002/hlca.19810640518

文献信息

• Highly enantioselective Michael addition reactions in water catalyzed by an insoluble MPS-supported 4-sulfonamidyl prolinol tert-butyldiphenylsilyl ether
  作者：Yongming Chuan、Guihua Chen、Yungui Peng

  DOI：10.1016/j.tetlet.2009.04.011

  日期：2009.6

  The development of a highly efficient, insoluble, and non-swelling MPS-supported organocatalyst for the direct asymmetric Michael reaction of ketones and aldehydes to nitrostyrenes at room temperature in water is described. Excellent yields (up to 100%) and high stereoselectivities (up to 94% dr and 93% ee) were achieved with 10 mol % of the catalyst. The resin-bound catalyst was simply separated and

  描述了一种高效，不溶且不溶胀的MPS负载的有机催化剂的开发，该有机催化剂用于在室温下在水中将酮和醛直接进行不对称迈克尔反应，生成硝基苯乙烯。使用10摩尔％的催化剂可获得极佳的收率（最高100％）和高的立体选择性（最高94％dr和93％ee）。树脂结合的催化剂可以简单地通过过滤进行分离和回收，然后再用于六个连续的试验中，而活性和对映选择性均不会显着下降。
• Organocatalyzed asymmetric Michael addition by an efficient bifunctional carbohydrate–thiourea hybrid with mechanistic DFT analysis
  作者：Chandra S. Azad、Imran A. Khan、Anudeep K. Narula

  DOI：10.1039/c6ob02158a

  日期：——

  core scaffold were synthesized and examined as catalysts for the asymmetric Michael addition reaction of aryl/alkyl trans-β-nitrostyrenes over cyclohexanone and other Michael donors having active methylene. Excellent enantioselectivities (<95%), diastereoselectivities (<99%), and yields (<99%) were attained under solvent free conditions using 10 mol% of 1d0. The obtained results were explained through

  合成了一系列以D-葡萄糖为核心骨架的硫脲基双功能有机催化剂，并研究了其作为芳基/烷基反式-β-硝基苯乙烯在环己酮和其他具有活性亚甲基的迈克尔供体上的不对称迈克尔加成反应的催化剂。在无溶剂条件下，使用10 mol％的1d 0可获得极好的对映选择性（<95％），非对映选择性（<99％）和产率（<99％）。通过使用B3LYP / 6-311G（d，p）// B3LYP / 6-31G（d）基本集的DFT计算来解释获得的结果。QM / MM计算揭示了在速率确定步骤中环己酮作为溶剂和反应物的作用，赋予了31.91 kcal mol -1 能量形成产品。
• Highly Efficient Amine Organocatalysts Based on Bispidine for the Asymmetric Michael Addition of Ketones to Nitroolefins
  作者：Zhigang Yang、Jie Liu、Xiaohua Liu、Zhen Wang、Xiaoming Feng、Zhishan Su、Changwei Hu

  DOI：10.1002/adsc.200800341

  日期：2008.9.5

  highly diastereoselective and enantioselective Michael addition of cyclohexanone, acetone and other ketones to nitroolefins was developed by the use of an amine organocatalyst based on bispidine. Additionally, a theoretical study of transition structures revealed that this bispidine-based primary-secondary amine catalyst could serve through an enamine intermediate and H-bond interaction, which was

  通过使用基于联吡啶的胺有机催化剂，开发了环己酮，丙酮和其他酮向硝基烯烃的高度非对映选择性和对映选择性迈克尔加成反应。另外，对过渡结构的理论研究表明，这种基于联吡啶的伯-仲胺催化剂可以通过烯胺中间体和氢键相互作用而起作用，这对于该反应的反应性和选择性很重要。
• 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。
• Highly Enantioselective Michael Additions in Water Catalyzed by a PS-Supported Pyrrolidine
  作者：Esther Alza、Xacobe C. Cambeiro、Ciril Jimeno、Miquel A. Pericàs

  DOI：10.1021/ol071366k

  日期：2007.9.1

  organocatalyst for the Michael addition of ketones to nitroolefins is described. A 1,2,3-triazole ring, constructed through a click 1,3-cycloaddition, plays the double role of grafting the chiral pyrrolidine monomer onto the polystyrene backbone and of providing a structural element, complementary to pyrrolidine, key to high catalytic activity and enantioselectivity. Optimal operation in water and full recyclability

  描述了用于酮向硝基烯烃的迈克尔加成的高效，聚合物负载的有机催化剂的开发。通过单击1,3-环加成反应构建的1,2,3-三唑环起着将手性吡咯烷单体接枝到聚苯乙烯骨架上并提供与吡咯烷互补的结构元素的双重作用，这是高催化活性的关键和对映选择性。在水中的最佳操作和充分的可循环利用性使三唑连接基对固定化有机催化剂具有吸引力。