N-(2-Hydroxy-2-methylpropyl)-phthalsaeureimid | 167108-05-6

• 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-(2-Hydroxy-2-methylpropyl)-phthalsaeureimid
• 英文别名: N-(β-hydroxy-isobutyl)-phthalimide；N-(β-Hydroxy-isobutyl)-phthalimid；N-(2-hydroxyisobutyl)-phthalimide；2-(2-hydroxyisobutyl)-phthalimide；2-(2-Hydroxy-2-methylpropyl)isoindole-1,3-dione
• CAS: 167108-05-6
• 化学式: C₁₂H₁₃NO₃
• 分子量: 219.24
• InChiKey: JMASLAZJPTVVNT-UHFFFAOYSA-N

物化性质

• 熔点：
  106-107 °C(Solv: ethanol (64-17-5))
• 沸点：
  361.6±25.0 °C(Predicted)
• 密度：
  1.284±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 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：

  盐酸 、 N-(2-Hydroxy-2-methylpropyl)-phthalsaeureimid 生成 N-(β-chloro-isobutyl)-phthalimide
  参考文献：
  名称：

  Dersin, Chemische Berichte, 1921, vol. 54, p. 3160

  摘要：

  DOI：
• 作为产物：
  描述：

  N-(三甲基硅基甲基)酰亚胺 在 盐酸 作用下， 生成 N-(2-Hydroxy-2-methylpropyl)-phthalsaeureimid
  参考文献：
  名称：

  A novel azomethine ylid forming photoreaction of N-trimethylsilylmethylphthalimides

  摘要：

  DOI：

  10.1016/s0040-4039(00)73798-1

文献信息

• Synthesis of β-phthalimido-alcohols via regioselective ring opening of epoxide by using reusable basic magnetic nano particles and their biological investigation
  作者：Mohammad Ali Zolfigol、Ahmad Reza Moosavi-Zare、Mahmoud Zarei、Abdolkarim Zare、Ehsan Noroozizadeh、Roya Karamian、Mostafa Asadbegy

  DOI：10.1039/c6ra07660b

  日期：——

  In this work, tetra butyl ammonium hydroxide ([Bu4N]OH) and magnetic nano particles (Fe3O4@SiO2@(CH2)3NH2) were introduced as efficient catalysts for the regioselective ring opening of epoxides including aromatic and aliphatic of epoxides to give the corresponding β-phthalimido-alcohols under mild conditions. A various range of β-phthalimido-alcohols as new compounds were prepared and fully characterized

  在这项工作中，引入四丁基氢氧化铵（[Bu 4 N] OH）和磁性纳米颗粒（Fe 3 O 4 @SiO 2 @（CH 2）3 NH 2）作为环氧化物的区域选择性开环的有效催化剂，包括在温和的条件下，形成环氧化物的芳族和脂肪族化合物，得到相应的β-邻苯二甲酰亚胺基醇。制备了各种范围的β-邻苯二甲酰亚胺醇作为新化合物，并通过IR，1 H和13对其进行了全面表征13 C NMR和质谱。还通过DPPH自由基清除测定法研究了合成的化合物的抗氧化性能。结果表明，与BHT（IC 50：0.122 mg mL -1）和抗坏血酸（IC 50：0.146 mg ）相比，所研究的β-邻苯二甲酰亚胺醇衍生物具有有效的抗氧化功能（IC 50：0.142–0.356 mg mL -1）。mL -1）作为标准。这可能是将来用于特殊用途的新型保健食品和药品补充剂。
• METHODS FOR PREPARING 2-METHOXYISOBUTYLISONITRILE AND TETRAKIS(2-METHOXYISOBUTYLISONITRILE)COPPER(I) TETRAFLUOROBORATE
  申请人：Morel Pierre

  公开号：US20080102028A1

  公开（公告）日：2008-05-01

  The present invention relates to new synthetic methods for preparing 2-methoxyisobutylisonitrile and metal isonitrile complexes, such as tetrakis(2-methoxyisobutylisonitrile)copper(I) tetrafluroroborate, which are used in the preparation of technetium ( 99m Tc) Sestamibi, and novel intermediate compounds useful in such methods.

  本发明涉及新的合成方法，用于制备2-甲氧基异丁基异腈和金属异腈络合物，例如四(2-甲氧基异丁基异腈)铜(I)四氟硼酸盐，这些化合物用于制备锝(99mTc)西斯他米和在此类方法中有用的新型中间体化合物。
• 一种绿色的可见光催化的乙酸酯化合物的制备方法
  申请人：苏州大学

  公开号：CN113754574A

  公开（公告）日：2021-12-07

  本发明公开了一种绿色的可见光催化的乙酸酯化合物的制备方法，该方法中以LED灯作为光源提供能量，经济易得的一、二、三级醇作为反应底物，三氟甲磺酸铈为催化剂，市场可购买的2,3‑丁二酮为原料。与现有技术相比较，本发明方法具有以下优点：1)采用绿色、温和、高效、节能、环境友好的可见光催化的反应模式；2)反应体系简单且底物范围广，一、二、三级醇均适用于该方法；3）无需添加脱水剂；4)反应产率较高；5)操作比较简单；6)原料廉价易得；7）反应可以实现克级规模及药物分子的后期修饰。
• [EN] BENZOHETEROCYCLIC COMPOUNDS
  申请人：OTSUKA PHARMACEUTICAL CO., LTD.

  公开号：WO1991005549A1

  公开（公告）日：1991-05-02

  (EN) Novel benzoheterocyclic compounds of formula (I), wherein R1 is H, halogen, alkyl, optionally substituted amino, alkoxy; R2 is H, halogen, alkoxy, phenylalkoxy, OH, alkyl, optionally substituted amino, carbamoyl-alkoxy, optionally substituted amino-alkoxy, optionally substituted benzoyloxy; R3 is a group: -NR4R5 or -CO-NR11R12; R4 is H, optionally substituted benzoyl, alkyl; R5 is a group $g(a) [R16 is halogen, optionally substituted alkyl, OH, alkoxy, alkanoyloxy, alkylthio, alkanoyl, carboxy, alkoxycarbonyl, CN, NO2, optionally substituted amino, phenyl, cycloalkyl, etc., or a group: -O-A-NR6R7; m is 0 to 3], phenyl-alkoxycarbonyl, alkanoyl, phenyl-alkanoyl, etc.; R11 is H or alkyl; R12 is cycloalkyl or optionally substituted phenyl; and W is a group: -(CH2)p (p is 3 to 5) or -CH=CH-(CH2)q (q is 1 to 3), the carbon atom of these groups being optionally replaced by 0, S, SO, SO2 or a group: -N(R13)- and further these groups having optionally 1 to 3 substituents of alkyl, alkoxycarbonyl, carboxy, OH, O, alkanoyloxy, etc., which have excellent vasopressin antagonistic activies and are useful as vasodilator, hypotensive agent, water diuretics, platelet agglutination inhibitor, and a vasopressin antagonistic composition containing the compound as the active ingredient.(FR) Nouveaux composés benzohétérocycliques de formule (I), dans laquelle R1 représente H, halogène, alkyle, amino éventuellement substitué, alcoxy; R2 représente H, halogène, alcoxy, phénylalcoxy, OH, alkyle, amino éventuellement substitué, carbamoyle-alcoxy, amino-alcoxy éventuellement substitué, benzoyloxy éventuellement substitué; R3 représente un groupe -NR4R5 ou -CO-NR11R12; R4 est H, benzoyle éventuellement substitué, alkyle; R5 est un groupe $g(a) [dans lequel R16 représente halogène, alkyle éventuellement substitué, OH, alcoxy, alcanoyloxy, alkylthio, alcanoyle, carboxy, alcoxycarbonyle, CN, NO2, amino éventuellement substitué, phényle, cycloalkyle, etc., ou un groupe -O-A-NR6R7; m est compris entre 0 et 3], phényl-alcoxycarbonyle, alcanoyle, phényl-alcanoyle, etc.; R11 représente H ou alkyle; R12 représente cycloalkyle ou phényle éventuellement substitué; et W est un groupe -CH2)p (p étant compris entre 3 et 5) ou -CH=CH-(CH2)q (q étant compris entre 1 et 3), l'atome de carbone de ces groupes étant éventuellement remplacé par 0, S, SO, SO2 ou un groupe -N(R13)-, ces groupes comportant éventuellement de 1 à 3 substituants d'alkyle, alcoxycarbonyle, carboxy, OH, O, alcanoyloxy, etc. Ces composés présentent d'excellentes activités antagonistes de la vasopressine et sont utiles en tant que vasodilateurs, agents hypotensifs, diurétiques et inhibiteurs d'agglutination de plaquettes. On décrit également une composition antagoniste de la vasopressine contenant ce composé en tant qu'ingrédient actif.

  新的苯并杂环化合物，其化学式为（I），其中R1为H，卤素，烷基，可选择取代的氨基，烷氧基；R2为H，卤素，烷氧基，苯基烷氧基，OH，烷基，可选择取代的氨基，氨基-卡巴莫基烷氧基，可选择取代的氨基-烷氧基，可选择取代的苯甲酰氧基；R3为一个基团：-NR4R5或-CO-NR11R12；R4为H，可选择取代的苯甲酰基，烷基；R5为一个基团$g(a) [其中R16为卤素，可选择取代的烷基，OH，烷氧基，烷酰氧基，烷硫基，烷酰基，羧基，烷氧羰基，CN，NO2，可选择取代的氨基，苯基，环烷基等，或一个基团：-O-A-NR6R7；m为0至3]，苯基-烷氧羰基，烷酰基，苯基-烷酰基等；R11为H或烷基；R12为环烷基或可选择取代的苯基；W为一个基团：-(CH2)p（p为3至5）或-CH=CH-(CH2)q（q为1至3），这些基团的碳原子可以选择性地被0，S，SO，SO2或一个基团：-N（R13）-替换，并且这些基团还可以具有1至3个取代基，如烷基，烷氧羰基，羧基，OH，O，烷酰氧基等，具有出色的抗利尿激素拮抗活性，并且可用作扩血管剂，降压剂，利尿剂，血小板凝聚抑制剂和含有该化合物的抗利尿激素拮抗剂组合物的活性成分。
• Novel and Efficient Azomethine Ylide Forming Photoreactions of N-(Silylmethyl)phthalimides and Related Acid and Alcohol Derivatives
  作者：Ung Chan Yoon、Dong Uk Kim、Chan Woo Lee、Young Sun Choi、Yean-Jang Lee、Herman L. Ammon、Patrick S. Mariano

  DOI：10.1021/ja00115a004

  日期：1995.3

  An investigation of the photochemistry of N-(silylmethyl)phthalimides and related alpha-phthaloylacetic acids and 2-phenylethanol derivatives has uncovered new excited state processes resulting in the formation of azomethine ylide intermediates. Irradiation of N-[(trimethylsilyl)methyl]phthalimide in MeCN promotes C to O silyl transfer to generate the corresponding azomethine ylide which is efficiently trapped by reaction with water to yield the N-methylphthalimide or by dipolar cycloaddition with acetone, methyl acrylate, or acrylonitrile. Cycloadditions with the latter two dipolarophiles are both regioselective and endo-stereoselective. These processes can be triplet photosensitized by use of acetophenone. The related N-[(trimethylsilyl)methyl]-1,8-naphthalimide reacts in a similar manner upon irradiation in MeCN solutions containing the dipolarophiles methyl acrylate and acrylonitrile to produce cycloadducts which undergo spontaneous elimination of TMSOH, yielding alpha,beta-unsaturated ester or nitrile products. The ylide formed by irradiation of the (silylmethyl)phthalimide is trapped in a stereospecific (retention) manner by the dipolarophiles trans-hex-4-en-3-one, dimethyl maleate, and dimethyl fumarate. The effect of aryl ring substitution on the regiochemical course of the photoinduced C to O silyl migration process was probed by use of the 4-methoxy- and 4-carbomethoxyl-N-(silylmethyl)phthalimides. Irradiation of the former substance in an MeCN solution containing acrylonitrile gives rise to a single adduct whose structure suggests that silyl migration to oxygen of the carbonyl meta to the OMe substituent is highly favored. In contrast, the 4-carbomethoxyphthalimide is converted under these conditions to a mixture of regioisomeric adducts. Thus, silyl migration in the excited state of this substance is nonselective. In accord with hints found in earlier observations made by Kanaoka (Chem. Pharm. Bull. 1982, 30, 1263), N-phthalimide derivatives of the alpha-amino acids glycine, alanine, and phenylalanine undergo similar ylide forming photoreactions upon irradiation in MeCN solutions. The azomethine ylides produced by photodecarboxylation of these substances are efficiently trapped by dipolarophiles, and the overall photoreactions starting with the alanine and phenylalanine derivatives are highly stereoselective. Finally, the N-phthalimide derivative of 2-amino-1-phenylethanol also is transformed to a related ylide upon irradiation in MeCN. The nature, regiochemical and stereochemical course, and mechanistic interpretation of these new azomethine ylide forming photoreactions are discussed in this publication.