3-(4'-nitrophenyl)isochromane | 214550-39-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 3-(4'-nitrophenyl)isochromane
• 英文别名: 3-(4-nitrophenyl)-3,4-dihydro-1H-isochromene
• CAS: 214550-39-7
• 化学式: C₁₅H₁₃NO₃
• 分子量: 255.273
• InChiKey: FXEKVOGCWSKQNJ-UHFFFAOYSA-N

物化性质

• 沸点：
  411.9±33.0 °C(Predicted)
• 密度：
  1?+-.0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  55
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(4'-nitrophenyl)isochromane 在 二甲基二环氧乙烷 、 三氯氧磷 作用下， 以 吡啶 、 丙酮 为溶剂， 反应 18.0h， 生成 3-(4-nitrophenyl)-1H-isochromen-1-one
  参考文献：
  名称：

  Oxidation of 3-arylisochromans by dimethyldioxirane. An easy route to substituted 3-arylisocoumarins

  摘要：

  The selective oxidation of the two different benzylethereal position of 3-arylisochromans by dimethyldioxirane as a function of different substituents on the aromatic rings was studied. The easy oxidation of these compounds was exploited for a new easy access to substituted 3-arylisocoumarins. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00917-5
• 作为产物：
  描述：

  2-(2-Hydroxymethyl-phenyl)-1-(4-nitro-phenyl)-ethanol 在 silica-immobilized p-TsOH 作用下， 以 氯仿 为溶剂， 反应 4.0h， 以64%的产率得到3-(4'-nitrophenyl)isochromane
  参考文献：
  名称：

  3,4-二氢-1H-2-苯并吡喃环闭合的改进程序。一般可获得3-取代的异色烷

  摘要：

  报道了使用负载在硅胶上的对-TsOH将1-取代的2-（-（羟甲基）-苯基乙醇闭环为3-取代的异色烷的一般方法。

  DOI：

  10.1016/s0040-4039(98)01417-8

文献信息

• Traceless Linkers for Solid-phase Synthesis. Homo- and Hetero-Diels-Alder Reactions of <i>o</i>-Quinodimethanes
  作者：Donald Craig、Michael J. Robson、Simon J. Shaw

  DOI：10.1055/s-1998-1968

  日期：1998.12

  The synthesis and Diels-Alder reactions of a polymer-supported o-quinodimethane are described. Reaction with dimethyl acetylenedicarboxylate, benzoquinone and trichloroacetonitrile as dienophiles gives respectively substituted naphthalenes or an isoquinoline off-resin, whilst reaction with aldehydes and imines gives polymer-supported benzodihydropyrans and tetrahydroisoquinolines. The latter heterocyclic products undergo Lewis or Brønsted acid-mediated cleavage reactions which allow incorporation of further functionality at the point of cleavage whilst leaving no trace of attachment to the polymer support.

  描述了聚合物支持的o-奎吡达美烯的合成及其Diels-Alder反应。与二甲基乙炔二羧酸酯、苯醌和三氯乙腈作为二烯亲体的反应分别生成取代的萘或离础的异喹啉，而与醛和亚胺的反应则生成聚合物支持的苯二氢吡喃和四氢异喹啉。后者的杂环产物经历路易斯或布朗斯特酸介导的裂解反应，这些反应允许在裂解点引入进一步的功能团，同时不留任何与聚合物支持的结合痕迹。
• Sultines as o-Quinodimethane Precursors in an Oxa-Diels–Alder Reaction: Synthesis of Functionalized Isochromans
  作者：Aurapat Ngamnithiporn、Padon Chuentragool、Poramate Songthammawat、Supakarn Punnita、Kittithuch Photong、Poonsakdi Ploypradith、Somsak Ruchirawat

  DOI：10.1055/a-2236-9589

  日期：——

  The development of an oxa-Diels–Alder reaction between sultines and carbonyl compounds is reported. o-Quinodimethanes, generated from sultines, undergo a [4+2]-cycloaddition with activated aldehydes or ketones in the presence of Cu(OTf)2 to provide a variety of functionalized isochromans, including spiroisochromans, in up to 99% yield. The developed protocol demonstrates broad functional-group compatibility

  据报道，磺胺类化合物和羰基化合物之间发生了 oxa-Diels-Alder 反应。由磺基磺胺产生的邻喹啉二甲烷在 Cu(OTf) 2存在下与活化的醛或酮进行 [4+2]-环加成，以提供各种官能化的异色满，包括螺异色满，产率高达 99%。所开发的方案表现出广泛的官能团兼容性，并耐受带有游离 NH 官能团的未受保护的靛红。
• Improved procedure for 3,4-dihydro-1H-2-benzopyran ring closure. A general access to 3-substituted isochromanes
  作者：Roberto Antonioletti、Paolo Bovicelli、Benedetta Crescenzi、Paolo Lupattelli

  DOI：10.1016/s0040-4039(98)01417-8

  日期：1998.9

  A general method for the ring closure of 1-substituted 2-(-hydroxymethyl)-phenylethanols to 3-substituted isochromanes using p-TsOH supported on silica gel is reported.

  报道了使用负载在硅胶上的对-TsOH将1-取代的2-（-（羟甲基）-苯基乙醇闭环为3-取代的异色烷的一般方法。
• Oxidation of 3-arylisochromans by dimethyldioxirane. An easy route to substituted 3-arylisocoumarins
  作者：Paolo Bovicelli、Paolo Lupattelli、Benedetta Crescenzi、Anna Sanetti、Roberta Bernini

  DOI：10.1016/s0040-4020(99)00917-5

  日期：1999.12

  The selective oxidation of the two different benzylethereal position of 3-arylisochromans by dimethyldioxirane as a function of different substituents on the aromatic rings was studied. The easy oxidation of these compounds was exploited for a new easy access to substituted 3-arylisocoumarins. (C) 1999 Elsevier Science Ltd. All rights reserved.