(R)-1-[1-(2-bromophenyl)-2-nitroethyl]cyclopentanecarbaldehyde | 1198362-19-4

• 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)-1-[1-(2-bromophenyl)-2-nitroethyl]cyclopentanecarbaldehyde
• 英文别名: (S)-1-[1-(2-bromophenyl)-2-nitroethyl]cyclopentanecarbaldehyde；1-[1-(2-bromophenyl)-2-nitroethyl]cyclopentanecarboxaldehyde
• CAS: 1198362-19-4
• 化学式: C₁₄H₁₆BrNO₃
• 分子量: 326.19
• InChiKey: ZTDLMIDKGDBTEP-GFCCVEGCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.57
• 重原子数：
  19.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  60.21
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  环戊基甲醛 、 o-bromonitrostyrene 在 (S)-1-(pyrrolidine-2-ylmethyl)-1H-pyrazole 、 苯甲酸 作用下， 以 neat (no solvent) 为溶剂， 反应 24.33h， 以94%的产率得到(R)-1-[1-(2-bromophenyl)-2-nitroethyl]cyclopentanecarbaldehyde
  参考文献：
  名称：

  吡咯烷-吡唑催化的α，α-二取代醛对硝基烯烃的对映选择性迈克尔加成

  摘要：

  为α的不对称催化Michael加成的高效的协议，α二取代的醛与吡咯烷吡唑nitroolefins进行说明。期望的产物γ-nitrocarbonyl化合物具有全碳季中心，是在良好的产率和高对映选择性的水平的无溶剂反应条件下获得的，使用苯甲酸作为添加剂。

  DOI：

  10.1016/j.tetasy.2014.06.009

文献信息

• ORGANOCATALYST
  申请人：Chen Kwunmin

  公开号：US20110040104A1

  公开（公告）日：2011-02-17

  The present invention provides an organocatalyst of formula (I), wherein R 1 is —H, —OH, —O—Si(R 4 )(R 5 )(R 6 ) or C 1-6 alkoxy, in which R 4 , R 5 and R 6 are identical or different and independently selected from the group consisting of C 1-6 alkyl, phenyl and phenyl substituted with C 1-6 alkyl; R 2 is —OH or ═O; X 1 is one selected from the group consisting of —NH—, —S— and X 2 is one selected from the group consisting of —C(═O)—, —CH 2 — and and X 1 is different from X 2 . The high yield and enantioselectivity of an addition reaction are obtained by using the organocatalyst of the present invention.

  本发明提供了一种式(I)的有机催化剂，其中R1为—H，—OH，—O—Si(R4)(R5)(R6)或C1-6烷氧基，其中R4、R5和R6相同或不同，并且独立地选自由C1-6烷基、苯基和苯基上取代的C1-6烷基的群；R2为—OH或═O；X1为从—NH—、—S—中选择的一种；X2为从—C(═O)—、—CH2—中选择的一种；X1与X2不同。通过使用本发明的有机催化剂，可以获得加成反应的高产率和对映选择性。
• Pyrrolidine–oxyimide catalyzed asymmetric Michael addition of α,α-disubstituted aldehydes to nitroolefins
  作者：Togapur Pavan Kumar

  DOI：10.1016/j.tetasy.2015.07.009

  日期：2015.9

  Organocatalytic enantioselective Michael addition of α,α-disubstituted aldehydes onto nitroolefins using pyrrolidine–oxyimide catalyst was reported. The reaction works effectively under neat conditions with 15 mol % of catalyst and 10 mol % of p-nitrobenzoic acid as an additive at 0 °C; this results in the formation of Michael adducts possessing an all-carbon quaternary center with good yields and

  报道了使用吡咯烷-氧酰亚胺催化剂将α，α-二取代醛有机催化对映选择性迈克尔加成到硝基烯烃上。该反应在纯净条件下在0°C下以15 mol％的催化剂和10 mol％的对硝基苯甲酸为添加剂可有效地进行；这导致形成具有全碳四元中心并具有良好收率和对映选择性的迈克尔加合物。
• Calixarene-based highly efficient primary amine–thiourea organocatalysts for asymmetric Michael addition of aldehydes to nitrostyrenes
  作者：Mustafa Durmaz、Abdulkadir Sirit

  DOI：10.1080/10610278.2013.773331

  日期：2013.5.1

  The synthesis of calix[4]arene-based chiral bifunctional primary amine–thiourea catalysts has been described from p-tert-butylcalix[4]arene for the first time. The calix[4]arene-based catalysts were successfully applied to promote Michael addition of aldehydes with nitroalkenes affording preferentially the (R)- or (S)-adducts in high yields (up to 95%) and excellent enantioselectivities (up to 99%

  首次描述了从对叔丁基杯[4]芳烃合成基于杯[4]芳烃的手性双功能伯胺-硫脲催化剂。杯[4]芳烃基催化剂被成功应用于促进醛与硝基烯烃的迈克尔加成，优先提供（R）-或（S）-加合物的高产率（高达95%）和优异的对映选择性（高达99%） es）。
• Pyrrolidinyl-Camphor Derivatives as a New Class of Organocatalyst for Direct Asymmetric Michael Addition of Aldehydes and Ketones to β-Nitroalkenes
  作者：Ying-Fang Ting、Chihliang Chang、Raju Jannapu Reddy、Dhananjay R. Magar、Kwunmin Chen

  DOI：10.1002/chem.201000483

  日期：——

  Practical and convenient synthetic routes have been developed for the synthesis of a new class of pyrrolidinyl–camphor derivatives (7 a–h). These novel compounds were screened as catalysts for the direct Michael addition of symmetrical α,α‐disubstituted aldehydes to β‐nitroalkenes. When this asymmetric transformation was catalyzed by organocatalyst 7 f, the desired Michael adducts were obtained in

  已经开发了实用且方便的合成路线来合成新型的吡咯烷基-樟脑衍生物（7 a–h）。筛选出这些新型化合物作为催化剂，将对称的α，α-二取代醛直接迈克尔加成至β-硝基烯烃。当该非对称转变是由有机催化剂催化的7 F，在高的化学产率得到所需的迈克尔加合物，具有高至优良的立体选择性（高达98：2非对映比（DR）和99％对映体过量（EE））。催化体系的范围已扩大到涵盖各种醛和酮作为供体来源。合成的应用由（S）-香茅醛，具有高立体选择性。
• Pyrrolidine-Camphor Derivative as an Organocatalyst for Asymmetic Michael Additions of α,α-Disubstituted Aldehydes to β-Nitroalkenes: Construction of Quaternary Carbon-Bearing Aldehydes under Solvent-Free Conditions
  作者：Chihliang Chang、Ssu-Hsien Li、Raju Jannapu Reddy、Kwunmin Chen

  DOI：10.1002/adsc.200800771

  日期：2009.6

  Abstractmagnified imageA novel pyrrolidine‐camphor organocatalyst 3 was designed, synthesized and proven to be an efficient catalyst for the asymmetric Michael reaction. Treatment of α,α‐disubstituted aldehydes with β‐nitroalkenes in the presence of 20 mol% organocatalyst 3 and 20 mol% benzoic acid under solvent‐free conditions provided the desired Michael product possessing an all‐carbon quaternary center with high chemical yields (up to 99% yield) and high levels of enantioselectivities (up to 95% ee).