exo-N-(p-tolyl)-3,6-epoxy-4-cyclohexene-1,2-dicarboximide | 74652-47-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: exo-N-(p-tolyl)-3,6-epoxy-4-cyclohexene-1,2-dicarboximide
• 英文别名: 4-p-tolyl-10-oxa-4-aza-tricyclo[5.2.1.0^2,6]dec-8-ene-3,5-dione；2-(p-tolyl)-3a,4,7,7a-tetrahydro-1H-4,7-epoxyisoindole-1,3(2H)-dione；(3aS,4R,7S,7aR)-2-(4-methylphenyl)-3a,4,7,7a-tetrahydro-4,7-epoxyisoindole-1,3-dione
• CAS: 74652-47-4
• 化学式: C₁₅H₁₃NO₃
• 分子量: 255.273
• InChiKey: LIKBYKYBCQAIMY-MPZDIEGVSA-N

物化性质

• 沸点：
  523.1±50.0 °C(Predicted)
• 密度：
  1.355±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 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：

  exo-N-(p-tolyl)-3,6-epoxy-4-cyclohexene-1,2-dicarboximide 在 sodium tetrahydroborate 、 碘 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 4.0h， 生成 C₁₇H₁₉NO₃
  参考文献：
  名称：

  Kotha, Sambasivarao; Pulletikurti, Sunil, Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 2020, vol. 59, # 12, p. 1868 - 1874

  摘要：

  DOI：
• 作为产物：
  描述：

  exo-3,6-epoxy-1,2,3,6-tetrahydrophthalic anhydride 、 乙烷,三氯氟- 在 (AcO)2O 、 manganese(II) acetate 、 三乙胺 作用下， 以 丙酮 为溶剂， 反应 3.0h， 以59.7%的产率得到exo-N-(p-tolyl)-3,6-epoxy-4-cyclohexene-1,2-dicarboximide
  参考文献：
  名称：

  1,3-偶极环加成反应：具有潜在抗肿瘤活性的取代芳香胺的5,6-脱氢降冰片烷衍生物的合成

  摘要：

  通过取代的芳族胺的5，6-脱氢降冰鸟烷素衍生物与腈氧化物的[3 + 2] 1，3-偶极环加成反应合成了十二种新化合物。所有化合物的结构和构型均通过1 H NMR，IR，MS，1 H- 1 HCOSY和NOESY光谱数据证实。他们的抗肿瘤活动正在进行中。

  DOI：

  10.1002/jhet.5570420103

文献信息

• 1,3-dipolar cycloaddition reaction: Synthesis and configuration of norcantharidin derivatives of substituted aromatic amine
  作者：Liping Deng、Yongzhou Hu

  DOI：10.1002/jhet.5570440314

  日期：2007.5

  A series of eighteen novel compounds that have potential pharmacological properties has been synthesized by 1,3-dipolar cycloaddition reactions of 5,6-dehydronorcantharidin derivatives of substituted aromatic amine with nitrile oxide. The synthesis was carried out following straightforward three-step procedure described herein. IR, 1H nmr and ms, H-H cosy and Noesy Cyclonoe, confirmed the structure

  通过取代的芳族胺的5，6-脱氢降冰鸟烷素衍生物与一氧化氮的1，3-偶极环加成反应合成了一系列具有潜在药理学特性的十八种新型化合物。按照本文所述的简单的三步法进行合成。红外，1 H nmr和ms，HH舒适和Noesy Cyclonoe分别确认了所有产品的结构。已经筛选了三个系列的去甲斑ari素类似物对HL60细胞的生物学评价。
• Norcantharidin analogues — Synthesis and evaluation of growth inhibition in a panel of selected tumor-cell lines
  作者：Liping Deng、Li Shen、Jing Zhang、Bo Yang、Qiaojun He、Yongzhou Hu

  DOI：10.1139/v07-082

  日期：2007.11.1

  A series of norcantharidin (NCTD) analogues have been synthesized by [3+2]1,3-dipolar cycloaddition reaction of norcantharidin derivatives of substituted aromatic amines with four nitrile oximes. All analogues have been screened for their antiproliferative activity in vitro against a panel of tumor cell lines: KB, SGC-7901, HL60, Bel-7402, HO-8910, and ECA109, producing IC₅₀ values from 0.36 µmol/L to >100 µmol/L. Compound 9d showed potency for the treatment of hepatoma, with IC₅₀ value to Bel-7402 cell line comparable to that of norcantharidin.Key words: norcantharidin analogues, isoxazoline, growth inhibition.

  通过取代芳香胺的去甲蒽醌衍生物与四种腈肟的［3+2］1,3-二极环加成反应，合成了一系列去甲蒽醌（NCTD）类似物。对所有类似物进行了体外抗肿瘤细胞系增殖活性筛选：这些化合物的 IC50 值从 0.36 µmol/L 到 100 µmol/L。化合物9d显示出治疗肝癌的效力，对Bel-7402细胞株的IC50值与去甲斑蝥素相当。
• Synthesis of novel pyrazole-linked norcantharidin derivatives of substituted aromatic amines with efficient 1,3-dipolar cycloaddition
  作者：Liping Deng、Yongzhou Hu

  DOI：10.1002/jhet.5570430646

  日期：2006.11

  Highly efficient, practical and convient synthesis of fifteen compounds by the [3+2] 1,3-dipolar cycloaddition reaction of norcantharidin derivatives of substituted aromatic amines with three hydrazines in the presence of Chloramine-T.

  在氯胺-T的存在下，通过取代的芳香族胺的降鸟th啶衍生物与三种肼的[3 + 2] 1,3-偶极环加成反应，可高效，便捷地合成十五种化合物。
• 1,3-Dipolar cycloaddition reaction: Synthesis of novel 5,6-dehydronorcantharidin derivatives of substituted aromatic amines with potential antitumor activities
  作者：Li-Ping Deng、Fang-Ming Liu、Hou-Yong Wang

  DOI：10.1002/jhet.5570420103

  日期：2005.1

  Twelve novel compounds were synthesized by the [3+2] 1,3-dipolar cycloaddition reaction of 5,6-dehydronorcantharidin derivatives of substituted aromatic amines with nitrile oxides. The structure and the configuration of all compounds were confirmed by 1H NMR, IR, MS, 1H-1HCOSY, and NOESY spectral data. Their anti-tumor activities are under way.

  通过取代的芳族胺的5，6-脱氢降冰鸟烷素衍生物与腈氧化物的[3 + 2] 1，3-偶极环加成反应合成了十二种新化合物。所有化合物的结构和构型均通过1 H NMR，IR，MS，1 H- 1 HCOSY和NOESY光谱数据证实。他们的抗肿瘤活动正在进行中。
• Synthesis of Novel Norcantharidin Derivatives of Substituted Aromatic Amines with Improved 1,3‐Dipolar Cycloaddition
  作者：Liping Deng、Yongzhou Hu

  DOI：10.1080/00397910500283404

  日期：2007.1.1

  Abstract Fourteen novel compounds were synthesized in a single step in good yield by the [3+2] 1,3‐dipolar cycloaddition reaction of norcantharidin derivatives of substituted aromatic amines with nitrile oximes in the presence of chloramine‐T as compared to the conventional method.

  摘要 与传统方法相比，在氯胺-T 存在下，取代芳香胺的降斑蝥素衍生物与腈肟发生 [3+2] 1,3-偶极环加成反应，一步合成了 14 种新化合物，收率良好。 .