(R)-3-(1-(3-chlorophenyl)-2-nitroethyl)pentane-2,4-dione | 1020665-79-5

• 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: (R)-3-(1-(3-chlorophenyl)-2-nitroethyl)pentane-2,4-dione
• 英文别名: (R)-3-[1-(3-chlorophenyl)-2-nitroethyl]pentane-2,4-dione；3-((R)-1-(3-chlorophenyl)-2-nitroethyl)pentane-2,4-dione
• CAS: 1020665-79-5
• 化学式: C₁₃H₁₄ClNO₄
• 分子量: 283.711
• InChiKey: MHRIDRUYJXQIRT-LBPRGKRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.49
• 重原子数：
  19.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  77.28
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  3-chloroβ-nitrostyrene 、 乙酰丙酮 在 [N-[(1R,2R)-2-(二甲基氨基)环己基]-N'-[[(1R,4AS,10AR)-1,2,3,4,4A,9,10,10A-八氢-1,4A-二甲基-7-异丙基-1-菲基]甲基]硫脲] 作用下， 以 甲苯 为溶剂， 反应 12.0h， 以96%的产率得到(R)-3-(1-(3-chlorophenyl)-2-nitroethyl)pentane-2,4-dione
  参考文献：
  名称：

  双官能松香衍生的硫代硫脲催化剂催化双立体控制方式下，将1,3-二羰基化合物对硝基和非对映选择性不对称加成至硝基烯烃。

  摘要：

  从可商购的天然松香衍生物开始，设计并合成了一类双官能松香衍生的胺硫脲催化剂。研究了将多种1,3-二羰基化合物双立体控制的不对称加成到硝基烯烃中。通过研究硫脲催化剂与已报道的其他硫脲催化剂的功效，已证明这些松香衍生的手性硫脲可作为该双酯控制的有机催化方法的有效催化剂。另外，这些手性硫脲配体容易获得。此外，

  DOI：

  10.1021/jo9009276

文献信息

• Novel ferrocene-based bifunctional amine–thioureas for asymmetric Michael addition of acetylacetone to nitroolefins
  作者：Xiaochen Ren、Chunyan He、Yingle Feng、Yonghai Chai、Wei Yao、Weiping Chen、Shengyong Zhang

  DOI：10.1039/c5ob00298b

  日期：——

  efficient method was developed to synthesize ferrocene-based bifunctional amine–thioureas bearing multiple hydrogen-bonding donors. Asymmetric Michael addition of acetylacetone to nitroolefins catalyzed by these novel bifunctional catalysts affords the Michael adducts in high yield and moderate to excellent enantioselectivities. Multiple hydrogen-bonds play an important role in accelerating the reaction.

  开发了一种有效的方法来合成带有多个氢键供体的二茂铁基双功能胺-硫脲。由这些新型双功能催化剂催化的乙酰丙酮不对称迈克尔加成到硝基烯烃上，可以高收率和中等至极好的对映选择性提供迈克尔加合物。多个氢键在加速反应中起重要作用。
• Chiral amine-thioureas bearing multiple hydrogen bonding donors: highly efficient organocatalysts for asymmetric Michael addition of acetylacetone to nitroolefins
  作者：Chun-Jiang Wang、Zhi-Hai Zhang、Xiu-Qin Dong、Xiao-Jun Wu

  DOI：10.1039/b718949d

  日期：——

  New bifunctional organocatalysts amine-thioureas bearing multiple hydrogen bonding donors were synthesized and applied in catalytic asymmetric Michael addition of acetylacetone to aryl and alkyl nitroolefins. Multiple hydrogen bonding donors play a significant role in accelerating reactions, improving yields and enantioselectivities.

  合成了具有多个氢键供体的新型双功能有机催化剂胺-硫脲，并将其用于乙酰丙酮催化芳基和烷基硝基烯烃的不对称迈克尔加成反应。多个氢键供体在加速反应，提高产率和对映选择性方面起着重要作用。
• Noncovalent Modification Strategy with Achiral Phosphoric Acid Diesters for Designing a Chiral Brønsted Base Organocatalyst
  作者：Momoko Hara、Aya Ogawa、Keiji Minagawa、Yasushi Imada、Yukihiro Arakawa

  DOI：10.1246/bcsj.20210462

  日期：2022.4.15

  A strategy for designing chiral Brønsted base organocatalysts through noncovalent modification of a chiral dibasic molecule with an achiral phosphoric acid diester is introduced for the first time. Such a molecular modification concept utilizing acid-base interactions may facilitate the on-demand design of asymmetric organocatalysts, as preliminarily demonstrated in this work.

  首次介绍了一种通过用非手性磷酸二酯对手性二元分子进行非共价修饰来设计手性 Brønsted 碱有机催化剂的策略。这种利用酸碱相互作用的分子修饰概念可以促进不对称有机催化剂的按需设计，正如这项工作中初步证明的那样。
• New class of bifunctional thioureas from l-proline: highly enantioselective Michael addition of 1,3-dicarbonyls to nitroolefins
  作者：Poopathy Vinayagam、Manjunatha Vishwanath、Venkitasamy Kesavan

  DOI：10.1016/j.tetasy.2014.02.011

  日期：2014.4

  A new class of bifunctional tertiary amine thiourea was synthesized from L-proline. The reported thiourea is amenable to steric and electronic modifications at the stereogenic center bearing a thiourea moiety. Excellent enantioselectivity was obtained in the Michael addition of 2,4-pentanedione to various nitro olefins using the new organocatalyst. The construction of contiguous stereocenters via the Michael reaction of substituted 1,3-dicarbonyls to nitro olefins was also carried out with very good yield, enantioselectivity, and diastereoselectivity. (C) 2014 Elsevier Ltd. All rights reserved.
• Cinchona–diaminomethylenemalononitrile organocatalyst for asymmetric conjugate addition of 1,3-diketone to nitroalkene
  作者：Shin-ichi Hirashima、Kosuke Nakashima、Yuki Fujino、Ryoga Arai、Takaaki Sakai、Masahiro Kawada、Yuji Koseki、Miho Murahashi、Norihiro Tada、Akichika Itoh、Tsuyoshi Miura

  DOI：10.1016/j.tetlet.2014.06.037

  日期：2014.8

  A diaminomethylenemalononitrile organocatalyst with a cinchona motif efficiently promotes the enantioselective conjugate addition of acetylacetone to various nitroalkenes to yield the corresponding addition products in high to excellent yields with up to 89% ee. (C) 2014 Elsevier Ltd. All rights reserved.