3-丁基-2,3-二氢异吲哚-1-酮 | 122654-56-2

• 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
• 中文名称: 3-丁基-2,3-二氢异吲哚-1-酮
• 中文别名: 丁苯酞杂质
• 英文名称: 3-n-butyl-2,3-dihydro-1H-isoindolin-1-one
• 英文别名: 3-butyl-2,3-dihydro-1H-isoindol-1-one；3-butylisoindolin-1-one；3-n-butyl-1-isoindolinone；(±)-3-n-butyl-2,3-dihydro-1H-isoindol-1-one；3-n-butyl isoindoline ketone；3-Butyl-isoindolin-1-on；NBI；1H-Isoindol-1-one, 3-butyl-2,3-dihydro-；3-butyl-2,3-dihydroisoindol-1-one
• CAS: 122654-56-2
• 化学式: C₁₂H₁₅NO
• 分子量: 189.257
• InChiKey: GMRHNUZCUUOQOX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  3-丁基-1(3H)-异苯并呋喃酮 在 hafnium tetrakis(trifluoromethanesulfonate) 、 草酰氯 、 palladium on activated carbon 、 5-methoxy-8-[N-(methyloxycarbonyl)amino]quinoline bound Cp*-Iridium complex 、 盐酸羟胺 、 氢气 、 potassium carbonate 、 四(3,5-二(三氟甲基)苯基)硼酸钠 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 、 水 、 乙酸乙酯 为溶剂， 80.0 ℃ 、101.33 kPa 条件下， 反应 42.5h， 生成 3-丁基-2,3-二氢异吲哚-1-酮
  参考文献：
  名称：

  Strategic Approach to the Metamorphosis of γ-Lactones to NH γ-Lactams via Reductive Cleavage and C–H Amidation

  摘要：

  A new approach has elaborated on the conversion of γ-lactones to the corresponding NH γ-lactams that can serve as γ-lactone bioisosteres. This approach consists of reductive C-O cleavage and an Ir-catalyzed C-H amidation, offering a powerful synthetic tool for accessing a wide range of valuable NH γ-lactam building blocks starting from γ-lactones. The synthetic utility was further demonstrated by the late-stage transformation of complex bioactive molecules and the asymmetric transformation.

  DOI：

  10.1021/acs.orglett.9b02673

文献信息

• A simple and convenient one-pot synthesis of substituted isoindolin-1-ones via lithiation, substitution and cyclization of <i>N'</i>-benzyl-<i>N,N</i>-dimethylureas
  作者：Keith Smith、Gamal A El-Hiti、Amany S Hegazy、Benson Kariuki

  DOI：10.3762/bjoc.7.142

  日期：——

  Lithiation of N'-benzyl-N,N-dimethylurea and its substituted derivatives with t-BuLi (3.3 equiv) in anhydrous THF at 0 °C followed by reaction with various electrophiles afforded a range of 3-substituted isoindolin-1-ones in high yields.

  在无水THF中，将N'-苄基-N,N-二甲基脲及其取代衍生物与t-BuLi（3.3当量）锂化，然后与各种亲电试剂反应，可以得到高产率的3-取代异吲哚啉酮。
• 3-N-BUTYL-1-ISOINDOLINONE AND USE THEREOF FOR PREVENTING OR TREATING CEREBRAL INFARCTION
  申请人：ZHAO Chunshun

  公开号：US20150183738A1

  公开（公告）日：2015-07-02

  3-n-Butyl-1-isoindolinone and use thereof for preventing or treating cerebral infarction. The compound is prepared by: 1) employing phthalimide as a starting reactant, contacting a nucleophilic Grignard reagent with the original reactant to add an alkyl group to a carbonyl carbon of an amide bond of the original reactant, thus yielding an intermediate; and 2) removing an oxygen atom connected to a third carbon atom of the intermediate in the presence of boron trifluoride diethyl etherate as a catalyst and triethylsilane as a reductant.

  3-n-丁基-1-异吲哚啉酮及其在预防或治疗脑梗死中的应用。该化合物的制备方法为：1）采用邻苯二甲酰亚胺作为起始反应物，将亲核格氏试剂与原始反应物接触，将烷基基团加到原始反应物的酰胺键的羰基碳上，从而得到中间体；2）在三氟化硼二乙醚酸催化剂和三乙基硅烷还原剂的存在下，去除中间体的第三个碳原子连接的氧原子。
• Asymmetric hydrogenolysis of racemic tertiary alcohols, 3-substituted 3-hydroxyisoindolin-1-ones
  作者：Mu-Wang Chen、Qing-An Chen、Ying Duan、Zhi-Shi Ye、Yong-Gui Zhou

  DOI：10.1039/c2cc16832d

  日期：——

  Asymmetric hydrogenolysis of racemic tertiary alcohols, 3-substituted 3-hydroxyisoindolin-1-ones, was developed using chiral phosphoric acid as catalyst and a Hantzsch ester as the hydrogen source with up to 95% ee. The reaction process of this asymmetric transfer hydrogenation may occur directly through the acyliminium ion intermediate.

  使用手性磷酸作为催化剂和 Hantzsch 酯作为氢源开发了外消旋叔醇（3-取代的 3-羟基异吲哚啉-1-酮）的不对称氢解，其 ee 高达 95%。这种不对称转移氢化的反应过程可以直接通过酰亚胺离子中间体发生。
• USE OF 3-N-BUTYL ISOINDOLINE KETONE IN PREPARATION OF DRUGS FOR PREVENTING AND TREATING CEREBRAL INFARCTION
  申请人：Sun Yat-Sen University

  公开号：EP2896611A1

  公开（公告）日：2015-07-22

  Disclosed is the use of the compound 3-n-butyl isoindoline ketone shown as formula I in the preparation of drugs for preventing and treating cerebral infarction. Since the compound has a structure of solid crystal, it has more freedom in terms of preparation, provides more choices for clinical medication and decreases medication costs, compared with the oily liquid form of the similar drug butylphthalide.

  本发明公开了式 I 所示化合物 3-正丁基异吲哚啉酮在制备预防和治疗脑梗塞药物中的用途。由于该化合物具有固态晶体结构，与同类药物丁苯酞的油状液态相比，制备自由度更高，为临床用药提供了更多选择，降低了用药成本。
• Synthesis of 3-alkyl-1-isoindolinones by alkylation of a benzotriazolyl substituted N-dimethylamino-phthalimidine
  作者：Eric Deniau、Dieter Enders

  DOI：10.1016/s0040-4020(01)00073-4

  日期：2001.3

  A convenient and versatile synthesis of 3-alkyl-2,3-dihydro-1H-isoindol-1-ones (isoindolinones) based upon sequential metalation, alkylation alpha to nitrogen and C,N-deprotection from 3-benzotriazolyl-2-dimethylamino-phthalimidine is described. (C) 2001 Elsevier Science Ltd. All rights reserved.