2-[(3-hydroxymethyl)phenyl]isoindoline-1,3-dione | 92789-55-4

• 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-[(3-hydroxymethyl)phenyl]isoindoline-1,3-dione
• 英文别名: 3-N-phthalimidobenzyl alcohol；N--phthalimid；N-(3-hydroxymethyl-phenyl)-phthalimide；2-[3-(Hydroxymethyl)phenyl]isoindole-1,3-dione
• CAS: 92789-55-4
• 化学式: C₁₅H₁₁NO₃
• 分子量: 253.257
• InChiKey: WMVFXFHZAQLFHT-UHFFFAOYSA-N

物化性质

• 熔点：
  149-151 °C
• 沸点：
  487.1±47.0 °C(Predicted)
• 密度：
  1.402±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  57.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-[(3-hydroxymethyl)phenyl]isoindoline-1,3-dione 在 四溴化碳 、 potassium carbonate 、 一水合肼 、 三乙胺 、 三苯基膦 、 potassium iodide 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 97.0h， 生成 31-Methyl-26-thia-1,8,16,23,31,35-hexazapentacyclo[21.5.5.13,7.110,14.117,21]hexatriaconta-3(36),4,6,10(35),11,13,17,19,21(34)-nonaene-9,15-dione
  参考文献：
  名称：

  双核大环化合物及其含二价离子的镍 (II) 羟基桥连和氰桥连配合物的合成：配体特征的解剖变异

  摘要：

  平面 NNN-钳形复合物 [M II (pyN 2 Me2 )(OH)] 1– (M II = Ni, Cu) 将 CO 2固定在 η 1 -OCO 2 H 复合物中；描述了铜系统的结果。Mn II、Fe II、Co II和Zn II表现不同，形成[M II (pyN 2 Me2 ) 2 ] 2–与N 4 O 2配位。将 Ni II钳并入双核大环2含有由两个 1,3-亚联苯基连接的三氨基 M II位点提供了近端 Ni II和 M II位点，用于研究 Ni-X-M 桥单元的合成、结构和反应性。这种配体结构被用作 M II原子和结合位点和桥 X = OH -和 CN -变化的参考，以产生具有改进特性的大环家族的其他成员。显示具有 22 元环的大环2以羟基桥键结合 M II = Mn、Fe 和 Cu。引入 4-Bu i O 基团（大环3) 提高了中性配合物的溶解度，例如那些具有 Ni II -OH-Cu

  DOI：

  10.1021/ic301506x
• 作为产物：
  描述：

  苯酐 、 3-氨基苯甲醇 以 甲苯 为溶剂， 以74%的产率得到2-[(3-hydroxymethyl)phenyl]isoindoline-1,3-dione
  参考文献：
  名称：

  在碱性条件下由醛和醇制备缩醛†

  摘要：

  已经报道了在碱性条件下由不可烯化的醛和醇合成乙缩醛的一种新的，简单的方案。醇钠与相应的三氟乙酸酯一起促进了这种反应，利用三氟乙酸钠的形成作为缩醛形成的驱动力。通过与各种酸敏感保护基团的正交性以及与官能团的良好相容性，证明该方案的实用性，在酸性条件下由醛类和醇类合成时，可提供合成有用的乙缩醛以补充合成。

  DOI：

  10.1039/c8ob00017d

文献信息

• Synthesis and Immunosuppressive Activity of New Mycophenolic Acid Derivatives
  作者：Karina Barbieri、Lucas Ercolin、Thierry Louat、Marisa Polesi、Chung Chin、Iracilda Zeppone、Jean Santos

  DOI：10.2174/1573406412666161207121226

  日期：2017.1.30

  diseases. Mycophenolic acid (MPA) and its derivatives are currently one of the most prescribed immunosuppressive drugs; however, metabolic drawbacks and variable interand intrapatient responses limit their use. Objective: In order to find out new safe and effective immunosuppressive compounds, we report here the synthesis and pharmacological evaluation of hybrid MPA derivatives containing the thalidomide/

  背景：免疫抑制药物被广泛用于预防和治疗同种异体移植排斥反应和自身免疫性疾病。霉酚酸（MPA）及其衍生物目前是处方最广泛的免疫抑制药物之一。但是，新陈代谢的缺陷和患者之间以及患者内部反应的差异限制了它们的使用。 目的：为了发现新的安全有效的免疫抑制化合物，我们在此报告含有沙利度胺/邻苯二甲酰亚胺亚基的杂化MPA衍生物的合成和药理学评价。 结果：与母体药物MPA和沙利度胺相比，所有化合物3a-d均具有增强的降低促炎细胞因子水平的能力。混合淋巴细胞反应试验已证明化合物3d-（E）-（3-（1,3-二氧代异吲哚啉-2-基）-2,6-二氧代哌啶-1-基）甲基-6-（4-羟基-6 -甲氧基-7-甲基-3-氧代-1,3-二氢异苯并呋喃-5-基）-4-甲基己基-4-烯酸酯-与MPA相比具有更好的活性。另外，化合物3d对Jurkat细胞的细胞毒性比MPA少，并且没有表现出体内遗传毒性作用。 结论：所有这些数
• NDIPhos as a platform for chiral supramolecular ligands in rhodium-catalyzed enantioselective hydrogenation
  作者：Guillaume Force、Robert J. Mayer、Marie Vayer、David Lebœuf

  DOI：10.1039/d3cc00695f

  日期：——

  Chiral naphthalene diimide ligands (NDIPhos) were exploited in rhodium-catalyzed enantioselective hydrogenation. The key feature of these ligands is their ability to self-assemble via π–π interactions to mimic bidentate ligands, offering a complementary method to traditional supramolecular strategies. This concept was further substantiated by computations with the composite electronic-structure method

  手性萘二酰亚胺配体 (NDIPhos) 被用于铑催化的对映选择性氢化。这些配体的关键特征是它们能够通过π-π 相互作用自组装以模拟双齿配体，为传统的超分子策略提供了一种补充方法。复合电子结构方法 r 2 SCAN-3c 的计算进一步证实了这一概念。
• Design, Synthesis, and Pharmacological Evaluation of Novel Hybrid Compounds To Treat Sickle Cell Disease Symptoms
  作者：Jean Leandro dos Santos、Carolina Lanaro、Lídia Moreira Lima、Sheley Gambero、Carla Fernanda Franco-Penteado、Magna Suzana Alexandre-Moreira、Marlene Wade、Shobha Yerigenahally、Abdullah Kutlar、Steffen E. Meiler、Fernando Ferreira Costa、ManChin Chung

  DOI：10.1021/jm200531f

  日期：2011.8.25

  A novel series of thalidomide derivatives (4a-f) designed by molecular hybridization were synthesized and evaluated in vitro and in vivo for their potential use in the oral treatment of sickle cell disease symptoms. Compounds 4a-f demonstrated analgesic, anti-inflammatory, and NO-donor properties. Compounds 4c and 4d were considered promising candidate drugs and were further evaluated in transgenic sickle cell mice to determine their capacity to reduce the levels of the proinflammatory cytokine tumor necrosis factor alpha (TNF alpha). Unlike hydroxyurea, the compounds reduced the concentrations of TNF alpha to levels similar to those induced with the control dexamethasone (300 mu mol/kg). These compounds are novel lead drug candidates with multiple beneficial actions in the treatment of sickle cell disease symptoms and offer an alternative to hydroxyurea treatment.
• Antiplatelet activity and TNF-α release inhibition of phthalimide derivatives useful to treat sickle cell anemia
  作者：Rafael C. Chelucci、Isabela J. de Oliveira、Karina P. Barbieri、Maria E. Lopes-Pires、Marisa C. Polesi、Diego E. Chiba、Iracilda Z. Carlos、Sisi Marcondes、Jean L. Dos Santos、ManChin Chung

  DOI：10.1007/s00044-019-02371-z

  日期：2019.8

  Sickle Cell Anemia (SCA) is one of the most prevalent hereditary hematological diseases worldwide. The disease is characterized by chronic inflammation, hypercoagulable state, and pro-thrombotic profile, which lead the vaso-occlusive process. In this work, we described the antiplatelet activity and the ability to reduce tumor necrosis factor-alpha (TNF-) levels of phthalimide derivatives. All compounds inhibited platelet aggregation induced by collagen and adenosine diphosphate, at levels ranging from 26.0 to 74.2% and 30.7 to 79.6%, respectively. The compounds exhibited reduced bleeding time compared to acetylsalicylic acid (ASA). Moreover, compounds 4c and 10c inhibited TNF- levels at 73.5% and 65.0%, respectively. These findings suggest that phthalimide derivatives 4c and 10c are promising lead compounds useful to prevent vaso-occlusion and inflammation associated with the sickle cell anemia.[GRAPHICS].
• Preparation of acetals from aldehydes and alcohols under basic conditions
  作者：Jakub Grabowski、Jarosław M. Granda、Janusz Jurczak

  DOI：10.1039/c8ob00017d

  日期：——

  A new, simple protocol for the synthesis of acetals under basic conditions from non-enolizable aldehydes and alcohols has been reported. Such reactivity is facilitated by a sodium alkoxide along with a corresponding trifluoroacetate ester, utilizing formation of sodium trifluoroacetate as a driving force for acetal formation. The usefulness of this protocol is demonstrated by its orthogonality with

  已经报道了在碱性条件下由不可烯化的醛和醇合成乙缩醛的一种新的，简单的方案。醇钠与相应的三氟乙酸酯一起促进了这种反应，利用三氟乙酸钠的形成作为缩醛形成的驱动力。通过与各种酸敏感保护基团的正交性以及与官能团的良好相容性，证明该方案的实用性，在酸性条件下由醛类和醇类合成时，可提供合成有用的乙缩醛以补充合成。