2-(cinnamyloxy)isoindoline-1,3-dione | 74771-11-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: 2-(cinnamyloxy)isoindoline-1,3-dione
• 英文别名: N-cinnamyloxyphthalimide；2-(3-phenylprop-2-enoxy)isoindole-1,3-dione
• CAS: 74771-11-2
• 化学式: C₁₇H₁₃NO₃
• 分子量: 279.295
• InChiKey: XMRVWQYRKHBXRR-UHFFFAOYSA-N

物化性质

• 熔点：
  117-119 °C
• 沸点：
  460.1±48.0 °C(Predicted)
• 密度：
  1.31±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(cinnamyloxy)isoindoline-1,3-dione 在 盐酸 、 一水合肼 作用下， 以 1,4-二氧六环 、 乙醇 、 乙酸乙酯 为溶剂， 反应 1.17h， 生成 O-(3-phenyl-2-propenyl)hydroxylamine hydrochloride
  参考文献：
  名称：

  使用通过肟基团的分子内反应开发腈氧化物与烯烃的区域选择性 [2 + 3] 环加成反应 [1]

  摘要：

  腈氧化物通过与烯烃的 [2 + 3] 环加成反应提供 2-异恶唑啉杂环。这些杂环可以转化为有用的中间体，例如 β-羟基酮和 γ-氨基醇，从而产生药物和农用化合物。然而，由于偶极子 HOMO 的能量降低，直接与羰基连接的腈氧化物显示出低反应性。此外，当使用不对称内烯烃时，区域选择性控制很困难。在此，我们设计了通过肟基团与烯烃结合的腈氧化物，并展示了它们的分子内 [2 + 3] 环加成反应。以高产率和单一区域异构体形式获得所需的环加合物。此外，通过在接头部分引入立体中心来实现面选择性环加成反应，

  DOI：

  10.1016/j.tet.2022.132833
• 作为产物：
  描述：

  肉桂醛 在 sodium tetrahydroborate 、 偶氮二甲酸二异丙酯 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 3.0h， 生成 2-(cinnamyloxy)isoindoline-1,3-dione
  参考文献：
  名称：

  O-alkylhydroxylamines as rationally-designed mechanism-based inhibitors of indoleamine 2,3-dioxygenase-1

  摘要：

  Indoleamine 2,3-dioxygenase-1 (IDO1) is a promising therapeutic target for the treatment of cancer, chronic viral infections, and other diseases characterized by pathological immune suppression. Recently important advances have been made in understanding IDO1's catalytic mechanism. Although much remains to be discovered, there is strong evidence that the mechanism proceeds through a heme-iron bound alkylperoxy transition or intermediate state. Accordingly, we explored stable structural mimics of the alkylperoxy species and provide evidence that such structures do mimic the alkylperoxy transition or intermediate state. We discovered that O-benzylhydroxylamine, a commercially available compound, is a. potent sub-micromolar inhibitor of IDO1. Structure activity studies of over forty derivatives of O-benzylhydroxylamine led to further improvement in inhibitor potency, particularly with the addition of halogen atoms to the meta position of the aromatic ring. The most potent derivatives and the lead, O-benzylhydroxylamine, have high ligand efficiency values, which are considered an important criterion for successful drug development. Notably, two of the most potent compounds demonstrated nanomolar-level cell-based potency and limited toxicity. The combination of the simplicity of the structures of these compounds and their excellent cellular activity makes them quite attractive for biological exploration of IDO1 function and antitumor therapeutic applications. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.12.028

文献信息

• nBu₄NI-catalyzed intermolecular C–O cross-coupling reactions: synthesis of alkyloxyamines
  作者：Yunhe Lv、Kai Sun、Tingting Wang、Gang Li、Weiya Pu、Nannan Chai、Huihui Shen、Yingtao Wu

  DOI：10.1039/c5ra12691f

  日期：——

  nBu₄NI-catalyzed cross-coupling of benzyl and allylic compounds with N-hydroxyphthalimide for the synthesis of alkyloxyamines were realized for the first time.

  nBu4NI催化的苄基和烯丙基化合物与N-羟基邻苯二甲酰亚胺的交叉偶联反应，首次实现了烷氧胺的合成。
• 2-(4,6-dimethoxy-2-pyrimidinyloxy)benzaldoximes, preparation processes
  申请人：Mitsui Toatsu Chemicals, Incorporated

  公开号：US04986846A1

  公开（公告）日：1991-01-22

  Disclosed are herbicidally active pyrimidine derivatives of the formula ##STR1## wherein R represents a hydrogen atom or an etherifying group, e.g., a lower alkyl, lower alkenyl, lower alkynyl, phenyl-substituted lower alkenyl, lower haloalkenyl, cycloalkyl, substituted phenyl-substituted lower alkenyl or phenyl-substituted lower alkynyl group; or a group represented by the following formula: ##STR2## wherein R.sup.1 represents a hydrogen atom or a lower alkyl group, X a halogen atom or a lower alkyl or lower alkoxyl group, m and n individually 0-2, and when m is 2, both Xs may be the same or different, and herbicidal compositions containing the same, alone or in combination with another herbicidally active compound, the pyrimidine derivatives being prepared by reaction of 2-(4,6-dimethoxy-2-pyrimidinyloxy)benzaldehyde with NH.sub.2 OR or with a salt of hydroxylamine followed by reaction with a halide of the formula RY wherein R has the same value as above and Y is Cl, Br or I.

  揭示了具有以下式的除草活性嘧啶衍生物##STR1##其中R代表氢原子或醚化基团，例如，较低的烷基，较低的烯基，较低的炔基，苯基取代的较低烯基，较低的卤代烯基，环烷基，取代的苯基取代的较低烯基或苯基取代的较低炔基；或由以下式表示的基团：##STR2##其中R.sup.1代表氢原子或较低的烷基，X代表卤原子或较低的烷基或较低的烷氧基，m和n分别为0-2，当m为2时，两个X可能相同或不同，并且含有这些衍生物的除草组合物，单独或与另一种除草活性化合物结合使用，所述嘧啶衍生物通过2-(4,6-二甲氧基-2-嘧啶氧基)苯甲醛与NH.sub.2 OR或与羟胺盐反应，然后与具有上述相同值的R的卤化物RY反应，其中Y为Cl，Br或I制备而成。
• Ultrasound accelerated synthesis of <i>O</i>-alkylated hydroximides under solvent- and metal-free conditions
  作者：Hongmei Jiang、Xiaoyue Tang、Sihan Liu、Lian Wang、Haicheng Shen、Jiankui Yang、Huixian Wang、Qing-Wen Gui

  DOI：10.1039/c9ob02245g

  日期：——

  A novel, sustainable, environmentally friendly, solvent-free and metal catalyst-free method for the CDC reaction between NHPI and benzyl/ether compounds is described.

  描述了一种新颖、可持续、环保、无溶剂和无金属催化剂的方法，用于NHPI和苄基/醚化合物之间的CDC反应。
• Alkene Oxyamination Using Malonoyl Peroxides: Preparation of Pyrrolidines and Isoxazolidines
  作者：Carla Alamillo-Ferrer、Jonathan M. Curle、Stuart C. Davidson、Simon C. C. Lucas、Stephen J. Atkinson、Matthew Campbell、Alan R. Kennedy、Nicholas C. O. Tomkinson

  DOI：10.1021/acs.joc.8b00392

  日期：2018.6.15

  functionalized pyrrolidines and isoxazolidines. This metal free alkene oxyamination proceeds in 50–85% yield and up to 13:1 trans-selectivity. In addition, the relative stereochemistry of the oxygen and nitrogen substituents can be inverted through an oxidation/reduction sequence or inverting the stereochemistry of the starting alkene. Mechanistic investigations show a higher reactivity for hydroxyl

  高烯丙基的治疗Ñ甲苯磺酰胺或烯丙基ñ -tosyl用的过氧化物malonoyl 1.5当量羟胺提供一种立体选择性的方法来访问官能吡咯烷和异恶唑烷。这种无金属的烯烃氧胺化反应收率可达50-85％，反式选择性高达13：1 。另外，氧和氮取代基的相对立体化学可以通过氧化/还原序列或起始烯烃的立体化学来反转。机理研究表明，羟基亲核试剂比磺酰胺亲核试剂具有更高的反应性，表明对双加氧反应的偏好高于对氧胺的反应。
• Pd^II -Catalyzed Oxidative Tandem aza-Wacker/Heck Cyclization for the Construction of Fused 5,6-Bicyclic N,O-Heterocycles
  作者：Chenghao Ye、Xuezhen Kou、Jingzhao Xia、Guoqiang Yang、Li Kong、Quhao Wei、Wanbin Zhang

  DOI：10.1002/asia.201800646

  日期：2018.8.6

  A PdII‐catalyzed oxidative tandem cyclization was developed for the construction of fused 5,6‐bicyclic N, O‐heterocycles. This reaction was enabled by the combined use of a 3‐methylpyridine ligand and pentafluorobenzoic acid additive. A range of heterocyclic products with different substituents could be prepared in moderate to good yields via this methodology. Several transformations, including a scaled‐up

  Pd II催化的氧化串联环化反应被开发用于构建稠合的5,6-双环N，O-杂环。通过联合使用3-甲基吡啶配体和五氟苯甲酸添加剂可以实现该反应。通过该方法，可以以中等到良好的产率制备一系列具有不同取代基的杂环产物。一些变革，包括产品的扩大规模的准备 2，也分别进行了展示我们的方法的良好的适用性。