N-methyl-10-oxabicyclo[2.2.1]hept-8-ene-3,endo-5-endo-dicarboximide | 99529-42-7

• 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: N-methyl-10-oxabicyclo[2.2.1]hept-8-ene-3,endo-5-endo-dicarboximide
• 英文别名: N-methyl-7-oxabicyclo[2.2.1]hept-5-ene-2-endo,3-endo-dicarboximide；endo,endo-N-methyl-7-oxanorborn-5-ene-2,3-dicarboximide；N-Methyl-7-oxanorbornenedicarbimide；(3aR,4R,7S,7aS)-2-methyl-3a,4,7,7a-tetrahydro-4,7-epoxyisoindole-1,3-dione
• CAS: 99529-42-7
• 化学式: C₉H₉NO₃
• 分子量: 179.175
• InChiKey: UFLZCUBVWZZTQZ-RNGGSSJXSA-N

物化性质

• 沸点：
  353.8±42.0 °C(Predicted)
• 密度：
  1.401±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 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：

  1-氯-2-碘苯 、 N-methyl-10-oxabicyclo[2.2.1]hept-8-ene-3,endo-5-endo-dicarboximide 在 甲酸 、 三苯胂 、 palladium diacetate 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以65%的产率得到N-methyl-exo-8-(2-chlorophenyl)-10-oxabicyclo[2.2.1]heptane-3-endo,5-endo-dicarboximide
  参考文献：
  名称：

  Reductive Heck Reactions of N-Methyl-substituted Tricyclic Imides

  摘要：

  研究了钯催化的N-甲基取代三环酰胺的氢芳基化，以寻找一种新的立体选择性合成一系列新的外部芳基（杂环芳基）取代的三环N-甲基酰胺的方法。

  DOI：

  10.3390/molecules15031303
• 作为产物：
  描述：

  endo,endo-2,3-dibromo-7-oxanorborneno<2,3-c>succinimide 在 氢气 、 银 、 锌 作用下， 以 四氢呋喃 为溶剂， 反应 0.08h， 以15%的产率得到N-甲基邻苯二甲酰亚胺
  参考文献：
  名称：

  伴随7-氧杂硼烷基邻二溴化物氢解的构型转化中烯烃中间体的证据

  摘要：

  的内切，ENDO -2,3-二溴-7- oxanorborneno [2,3-C]琥珀酰亚胺（1）经历在所述溴取代基的氢解形式（完整的反转5）（锌/银夫妇在THF）或（26）（H 2，Pd / C）。在锌/银偶合实验中，用呋喃捕集，显示出高反应性的亲双烯体N-甲基7-氧杂硼烷二烯[2,3-c]马来酰亚胺（3）是一种瞬时中间体。氘标记实验已用于帮助阐明这些反应的机制。

  DOI：

  10.1016/0040-4039(94)85227-8

文献信息

• [EN] BORONIC ESTER PRODRUGS AND USES THEREOF<br/>[FR] PROMÉDICAMENTS D'ESTER BORONIQUE ET LEURS UTILISATIONS
  申请人：MASSACHUSETTS INST TECHNOLOGY

  公开号：WO2020236253A1

  公开（公告）日：2020-11-26

  Disclosed herein are compounds of Formula (I) or (II). The compounds include an agent (e.g., pharmaceutical agent, cosmetic agent, or nutraceutical agent) through a linker that includes a boronic ester moiety in the backbone of the linker. The compounds may be monomers. Also provided are polymers prepared by polymerizing the monomers. The polymers may be useful for delivering the agent to a subject, tissue, biological sample, or a cell. Also provided are methods of preparing the polymers, compositions and kits comprising the polymers, and methods of use (e.g., use in delivering the agent, treating a disease, preventing a disease, diagnosing a disease) involving the polymers or compositions. The structure of the boronic ester moiety may be fine tuned so that the properties related to delivery to a subject, biological sample, tissue, or cell may be fine tuned.

  本文披露了化合物的化学式(I)或(II)。这些化合物包括通过含有硼酸酯基团的连接剂（例如，药物剂、化妆品剂或营养剂）连接的活性物质。这些化合物可以是单体。还提供了通过聚合单体制备的聚合物。这些聚合物可能用于将活性物质传递给受试者、组织、生物样本或细胞。还提供了制备这些聚合物的方法、包含这些聚合物的组合物和试剂盒，以及涉及这些聚合物或组合物的使用方法（例如，用于传递活性物质、治疗疾病、预防疾病、诊断疾病）。硼酸酯基团的结构可以进行微调，以便微调与传递给受试者、生物样本、组织或细胞相关的性质。
• A new stable Hoveyda–Grubbs catalyst with mixed anionic ligands
  作者：Kati Vehlow、Simon Maechling、Katrin Köhler、Siegfried Blechert

  DOI：10.1016/j.tetlet.2006.09.096

  日期：2006.11

  and characterisation of a new highly active Hoveyda–Grubbs 2nd generation type catalyst is described. Substitution of one chloride ligand with a partially fluorinated trialkoxysilyl substituted carboxylate leads to the stable monocarboxylate ruthenium catalyst (3). This catalyst represents the first example of a stable and isolable mono-chloride exchanged carboxylate complex suitable for both homogeneous

  描述了新型高活性Hoveyda-Grubbs第二代催化剂的合成和表征。一种氯化物配体被部分氟化的三烷氧基甲硅烷基取代的羧酸酯取代产生稳定的单羧酸酯钌催化剂（3）。该催化剂代表了适用于均相和异相复分解的稳定且可分离的一氯化物交换的羧酸盐配合物的第一个实例。在代表性的复分解反应中测试了新催化剂的反应性，并提供了与母体二氯化物体系（1）相当的活性。
• Structural Studies on Cycloadducts of Furan, 2-Methoxyfuran, and 5-Trimethylsilylcyclopentadiene with Maleic Anhydride and <i>N</i>-Methylmaleimide
  作者：Yit Wooi Goh、Brett R. Pool、Jonathan M. White

  DOI：10.1021/jo7018575

  日期：2008.1.1

  of the C−C bonds that break in this reaction is clearly related to the known reactivity of these cycloadducts toward this reaction. In the structures of the cycloadducts 21 and 22 derived from 2-methoxyfuran, the early stages of an alternative fragmentation reaction are apparent, consistent with the reactivity of these compounds in solution.

  逆Diels-Alder反应的早期在呋喃或5-三甲基甲硅烷基环戊二烯与马来酸酐和N-甲基马来酰亚胺之间形成的环加合物的结构中很明显。在该反应中断裂的CC键的加长程度显然与这些环加合物对该反应的已知反应性有关。在衍生自2-甲氧基呋喃的环加合物21和22的结构中，替代的裂解反应的早期阶段是显而易见的，这与这些化合物在溶液中的反应性一致。
• Unusual stability of N-methylmaleimide cycloadducts: characterization of isobenzofuran retro-Diels-Alder reactions
  作者：David Tobia、Roy Harrison、Brian Phillips、Thomas L. White、Marcello DiMare、Bruce Rickborn

  DOI：10.1021/jo00076a032

  日期：1993.11

  Many years ago Diels and Thiele noted the unusual stability of maleic anhydride cycloadducts and employed this feature in scavenging anthracene generated in a retro-[4 + 2] reaction. N-methylmaleimide, although nearly identical to maleic anhydride in rates of Diels-Alder reactions, forms even more stable cycloadducts. The rate constants for the four reactions that characterize the furan/N-methylmaleimide system were measured under the conditions used by Lee and Herndon to study the furan/maleic anhydride system. Comparison of the two dienophiles indicates that N-methylmaleimide adducts are ca. 3 kcal.mol-1 more stable than the corresponding exo- and endo-maleic anhydride adducts. Somewhat larger (ca. 4 +/- 0.5 kcal.mol-1) differences in stability were found for the cycloadducts of the much more reactive diene isobenzofuran. N-Methylmaleimide is used as a diene scavenger to obtain rate constants for retro-Diels-Alder reactions of isobenzofuran adducts with maleic anhydride and some substituted analogs. The rates of retro-Diels-Alder reactions of substituted N-methylmaleimide adducts were also determined by an alternative method. The substituents examined enhance the rates of exo retro-Diels-Alder reactions by factors of 15-40, while endo adduct retro-Diels-Alder rates are only slightly affected. Calculations were done at the MP2/6-31G*//HF/6-31G* level to compare the heats of hydrogenation of maleic anhydride and maleimide. The reduction of maleimide is calculated to be 2.5 kcal.mol-1 more exergonic, supporting the experimental observations.
• Goksu, Gokce; Ocal, Nuket, Acta Chimica Slovenica, 2011, vol. 58, # 2, p. 256 - 261
  作者：Goksu, Gokce、Ocal, Nuket

  DOI：——

  日期：——