4-亚硝基二苯基醚 | 52671-42-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 4-亚硝基二苯基醚
• 中文别名: 3-吡啶羧酸,5-[2-(2,5-二氯苯基)二氮烯基]-1,2-二氢-4,6-二羟基-2-羰基-1-苯基-,甲基酯
• 英文名称: 4-nitrosophenyl phenyl ether
• 英文别名: 1-nitroso-4-phenoxybenzene；1-phenoxy-4-nitrosobenzene；4-phenoxynitrosobenzene
• CAS: 52671-42-8
• 化学式: C₁₂H₉NO₂
• mdl: MFCD01657486
• 分子量: 199.209
• InChiKey: AFZZWGLJNSCSAH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  38.7
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2909309090

反应信息

• 作为反应物：
  描述：

  4-亚硝基二苯基醚 在 4-二甲氨基吡啶 、 diisopropyl aluminum 2,6-di-tert-butyl-4-methylphenoxide 、 溶剂黄146 、 三乙胺 、 (S)-5-(吡咯烷-2-基)-1H-四唑 作用下， 以 二氯甲烷 、 甲苯 、 乙腈 为溶剂， 反应 27.0h， 生成
  参考文献：
  名称：

  Diastereo- and Enantioselective Synthesis of Nitroso Diels−Alder-Type Bicycloketones Using Dienamine:  Mechanistic Insight into Sequential Nitroso Aldol/Michael Reaction and Application for Optically Pure 1-Amino-3,4-diol Synthesis

  摘要：

  This article presents complete diastereo- and highly enantioselective synthesis of nitroso Diels-Alder-type bicycloketones using dienamine. With the hydrogen bonding of two hydroxyls in the bulky binaphthol 1c, high enantioselectivities and complete diastereoselectivity are realized in 2-oxa-3-aza-bicycloketone synthesis. On the other hand, alpha,beta-unsaturated ketone can be employed as diene precursor, utilizing readily available tetrazole catalyst 3b, to provide the 3-oxa-2-aza-bicycloketones in moderate yields with complete enantioselectivities. Investigation into the reaction utilizing 2-morpholino-4,4-diphenylcyclohexadiene 2d clearly indicated that cyclization with the bulky binaphthol 1c is involved in the sequential process, the N-nitroso aldol reaction, followed by Michael addition. In addition, optically pure 1-amino-3,4-diol is synthesized from 2-oxa-3-aza-bicycloketones. Use of p-phenoxynitrosobenzene allows access to protected amino diol via cleavage of the N-Ph bond.

  DOI：

  10.1021/ja066037m
• 作为产物：
  描述：

  对硝基二苯醚 生成 4-亚硝基二苯基醚
  参考文献：
  名称：

  Electron Spin Resonance Studies of a Stable Arylnitroso—Olefin Adduct Free Radical¹

  摘要：

  DOI：

  10.1021/jo01347a018

文献信息

• A Highly Stereoselective Organocatalytic Tandem Aminoxylation/Aza-Michael Reaction for the Synthesis of Tetrahydro-1,2-Oxazines
  作者：Di Zhu、Min Lu、Pei Juan Chua、Bin Tan、Fei Wang、Xinhao Yang、Guofu Zhong

  DOI：10.1021/ol801864c

  日期：2008.10.16

  stereoselective synthesis of multifunctionalized tetrahydro-1,2-oxazines (THOs) has been achieved by the organocatalyzed asymmetric tandem alpha-aminoxylation/aza-Michael reaction for the C-O/C-N bond formations in moderate to good yields with excellent diastereo- (>99:1 dr) and enantioselectivities (92% to >99% ee).

  通过有机催化的不对称串联α-氨基羟化/氮杂-迈克尔反应，以适中至良好的收率，具有优异的非对映异构性，可以轻松实现多官能化四氢-1,2-恶嗪（THOs）的立体选择性合成。 99：1 dr）和对映选择性（92％到> 99％ee）。
• Synthesis of dihydrobenzoxazine pyrrolidone spirocyclic compounds
  作者：Wenqin Liu、Heng Yang、Bing Sun、Fang-Lin Zhang、Dandan Liu、Hua Zheng

  DOI：10.1016/j.tetlet.2018.08.031

  日期：2018.9

  A simple and efficient synthetic strategy for the preparation of dihydrobenzoxazine spirocyclic compounds was reported via the cycloaddition reaction of o-succinimide-substituted benzaldehyde with nitrobenzene. The reactions can be conducted under very mild reaction conditions (room temperature) using 10 mol% of Cs2CO3 as catalyst. A series of dihydrobenzoxazine pyrrolidone spirocyclic compounds were

  通过邻琥珀酰亚胺取代的苯甲醛与硝基苯的环加成反应，报道了一种简单有效的合成二氢苯并恶嗪螺环化合物的合成策略。该反应可以在非常温和的反应条件（室温）下进行，使用10mol％的Cs 2 CO 3作为催化剂。以中等至良好的产率提供了一系列二氢苯并恶嗪吡咯烷酮螺环化合物。该策略为合成和研究二氢苯并恶嗪吡咯烷酮螺环化合物的生物活性提供了新的方向。
• Asymmetric Hetero Diels-Alder Reaction of Nitroso Compounds Utilizing Tartaric Acid Ester as a Chiral Auxiliary
  作者：Katsuhiko Inomata、Hiroki Sakai、Xia Ding、Tetsusuke Yoshida、Shuhei Fujinami、Yutaka Ukaji

  DOI：10.3987/com-08-s(n)94

  日期：——

  enantioselective hetero Diels-Alder reaction of a nitroso compound with a cyclic dienol, cyclohexa-l,3-dienylmethanol, has been realized utilizing stoichiometric amount of tartaric acid ester as a chiral auxiliary to afford the corresponding dihydro-1,2-oxazine with complete regioselectivity and high enantioselectivity of up to 92% ee. A catalytic version of the asymmetric hetero Diels-Alder reaction of nitroso

  利用化学计量的酒石酸酯作为手性助剂，实现了亚硝基化合物与环状二烯醇环己醇-1,3-二烯基甲醇的区域和对映选择性杂狄尔斯-阿尔德反应，得到相应的二氢-1,2 -恶嗪具有完全的区域选择性和高达 92% ee 的高对映选择性。还实现了亚硝基化合物与二烯醇的不对称杂 Diels-Alder 反应的催化形式，以提供高达 83% ee 的相应光学活性环加合物。添加 MS 4A 对于实现可重现的高对映选择性至关重要。
• Tetrahydroquinolines via Stereospecific [3 + 3]-Annulation of Donor–Acceptor Cyclopropanes with Nitrosoarenes
  作者：Saikat Das、Shyamal Chakrabarty、Constantin G. Daniliuc、Armido Studer

  DOI：10.1021/acs.orglett.6b01302

  日期：2016.6.3

  A stereospecific [3 + 3]-annulation of donor–acceptor cyclopropanes with nitrosoarenes under the influence of MgBr2 as a stoichiometric Lewis acid and reagent offers a novel approach to various structurally diverse C-8-brominated tetrahydroquinolines. In these cascades C–C, C–N, and C–Br bonds are formed. The reactions are easy to conduct and proceed under mild conditions, and the products can readily

  在MgBr 2作为化学计量的路易斯酸和试剂的作用下，亚硝基芳烃与立体异构[3 + 3]环化的亚硝基芳烃为各种结构多样的C-8溴化四氢喹啉提供了一种新颖的方法。在这些级联中，形成C–C，C–N和C–Br键。该反应易于进行并在温和的条件下进行，并且产物可以容易地进一步功能化，从而使该方法具有很高的价值。
• Multicomponent 1,3-Bifunctionalization of Donor–Acceptor Cyclopropanes with Arenes and Nitrosoarenes
  作者：Saikat Das、Constantin G. Daniliuc、Armido Studer

  DOI：10.1021/acs.orglett.6b02815

  日期：2016.11.4

  AlBr3-mediated multicomponent 1,3-bifunctionalization of donor–acceptor cyclopropanes using arenes and nitrosoarenes as coupling partners is presented. In the cascade, a C–C, a C–N, and a C–Br bond is formed. Reactions are easy to conduct and proceed under mild conditions. The γ,γ-disubstituted N-arylated α-amino esters obtained as products are readily further chemically modified rendering the method

  介绍了使用芳烃和亚硝基芳烃作为偶联伙伴的AlBr 3介导的供体-受体环丙烷的多组分1,3-双官能化。在级联反应中，形成一个C–C，一个C–N和一个C–Br键。反应易于进行，并在温和的条件下进行。作为产物获得的γ，γ-二取代N-芳基化α-氨基酯很容易进一步化学修饰，使该方法有价值。