丁苯酞标准品020 | 20871-32-3

• 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: 丁苯酞标准品020
• 英文名称: 3-butyl 3-hydroxyisoindolin-1-one
• 英文别名: 3-butyl-3-hydroxyisoindolin-1-one；3-butyl-3-hydroxy-2,3-dihydro-isoindol-1-one；3-Hydroxy-3-butylphthalimidine；3-butyl-3-hydroxy-2H-isoindol-1-one
• CAS: 20871-32-3
• 化学式: C₁₂H₁₅NO₂
• 分子量: 205.257
• InChiKey: IRGFMBXWPHRCFP-UHFFFAOYSA-N

物化性质

• 沸点：
  443.2±44.0 °C(Predicted)
• 密度：
  1.159±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  15
• 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：
  49.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  丁苯酞标准品020 在 盐酸 、 sodium cyanoborohydride 作用下， 以 甲醇 为溶剂， 生成 3-丁基-2,3-二氢异吲哚-1-酮
  参考文献：
  名称：

  Asymmetric hydrogenolysis of racemic tertiary alcohols, 3-substituted 3-hydroxyisoindolin-1-ones

  摘要：

  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。

  DOI：

  10.1039/c2cc16832d
• 作为产物：
  描述：

  溴丁基-镁 、 邻苯二甲酸亚胺 在 氯化铵 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以97%的产率得到丁苯酞标准品020
  参考文献：
  名称：

  3-N-BUTYL-1-ISOINDOLINONE AND USE THEREOF FOR PREVENTING OR TREATING CEREBRAL INFARCTION

  摘要：

  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。

  公开号：

  US20150183738A1

文献信息

• Influence of <i>N</i> ‐Substitution in 3‐Alkyl‐3‐hydroxyisoindolin‐1‐ones on the Stereoselectivity of Brønsted Acid‐Catalyzed Synthesis of 3‐Methyleneisoindolin‐1‐ones
  作者：Nikola Topolovčan、Filip Duplić、Matija Gredičak

  DOI：10.1002/ejoc.202100400

  日期：2021.7.26

  Brønsted acid-catalyzed dehydration of 3-alkyl-3-hydroxyisoindolin-1-ones is discussed. The reaction is efficiently catalyzed by methanesulfonic acid in acetonitrile and provides the corresponding 3-methyleneisoindolin-1-ones. The E/Z stereochemistry around the exocyclic double bond is in strong correlation with the size of the N-substituent. Selective formation of only one stereoisomer can be controlled

  讨论了 3-烷基-3-羟基异吲哚啉-1-酮的布朗斯台德酸催化脱水。该反应由甲磺酸在乙腈中有效催化，并提供相应的 3-亚甲基异吲哚啉-1-酮。所述ë / Ž周围环外双键的立体化学是在与所述的尺寸很强的相关性ñ -取代。仅一种立体异构体的选择性形成可以通过改变合成步骤的顺序来控制。
• Chiral Brønsted Acid Catalyzed Enantioselective aza-Friedel–Crafts Reaction of Cyclic α-Diaryl <i>N</i>-Acyl Imines with Indoles
  作者：Danijel Glavač、Chao Zheng、Irena Dokli、Shu-Li You、Matija Gredičak

  DOI：10.1021/acs.joc.7b01420

  日期：2017.8.18

  Asymmetric addition of indoles to cyclic α-diaryl-substituted N-acyl imines, which are generated in situ from 3-aryl 3-hydroxyisoindolinones, is described. The transformation proceeds smoothly with a broad range of indoles and isoindolinone alcohols using a SPINOL-derived chiral Brønsted acid catalyst to afford α-tetrasubstituted (3-indolyl)(diaryl)methanamines in excellent yields and enantioselectivities

  描述了将吲哚不对称地加成到环状α-二芳基取代的N-酰基亚胺上，所述环状α-二芳基取代的N-酰基亚胺是由3-芳基3-羟基异吲哚满酮原位产生的。使用SPINOL衍生的手性布朗斯台德酸催化剂，可在多种吲哚和异吲哚啉酮醇中顺利进行转化，从而以极佳的收率和对映选择性（高达98％的收率，最高可达98％的收率）提供α-四取代的（3-吲哚基）（二芳基）甲胺。 > 99：1 er）。DFT计算和实验数据支持了立体化学诱导的起源。
• Organocatalyzed Enantioselective Synthesis of Quaternary Carbon-Containing Isoindolin-1-ones
  作者：Xiaolei Yu、Youming Wang、Guiping Wu、Haibin Song、Zhenghong Zhou、Chuchi Tang

  DOI：10.1002/ejoc.201100163

  日期：2011.6

  corresponding quaternary carbon-containing 3,3-disubstituted isoindolin-1-ones in good yields (up to 99 %) with good to excellent enantioselectivities (up to 95 % ee). The optical purity of the product was further improved after a single recrystallization. This protocol provides a convenient method for the catalytic asymmetric synthesis of valuable 3,3-disubstituted isoindolin-1-ones in high yields

  3,3'-三苯基甲硅烷基取代的 (S)-BINOL-基（1,1'-bi-2-萘酚）磷酸已被证明是一种有效的有机催化剂，用于吲哚与 3-取代 3 的不对称 Friedel-Crafts 烷基化-羟基异吲哚啉-1-酮，以良好的产率（高达 99%）提供相应的含季碳的 3,3-二取代异吲哚啉-1-酮，具有良好至极好的对映选择性（高达 95% ee）。单次重结晶后产物的光学纯度进一步提高。该协议为以高产率和对映选择性催化不对称合成有价值的 3,3-二取代异吲哚啉-1-酮提供了一种方便的方法。
• A Practical Two‐Step Synthesis of 3‐Alkyl‐2,3‐dihydro‐1<i>H</i>‐isoindolin‐1‐ones
  作者：Yuan‐Ping Ruan、Ming‐De Chen、Ming‐Zhu He、Xiang Zhou、Pei‐Qiang Huang

  DOI：10.1081/scc-120028358

  日期：2004.12.31

  A flexible approach to 3-alkyl-2,3-dihydro-1H-isoindolin-1-ones via the reductive-alkylation procedure is described. Present method is versatile in scope, allowing the easy introduction of various C-3 carbon -substituents by Grignard addition to phthalimide.
• Discovery of 3-n-butyl-2,3-dihydro-1H-isoindol-1-one as a potential anti-ischemic stroke agent
  作者：Chunshun Zhao、Zujian Lan、Xiaoyu Xu、Xuefei Zhang、Ming Lei、Wenkai Xu、Jin Li、Zengrong Liang

  DOI：10.2147/dddt.s84731

  日期：——

  To develop novel anti-ischemic stroke agents with better therapeutic efficacy and bioavailability, we designed and synthesized a series of 3-alkyl-2,3-dihydro-1H-isoindol-1-ones compounds (3a-i) derivatives, one of which (3d) exhibited the strongest inhibitory activity for the adenosine diphosphate-induced and arachidonic acid-induced platelet aggregation. This activity is superior to that of 3-n-butylphthalide and comparable with aspirin and edaravone. Meanwhile, 3d not only exhibited a potent activity in scavenging free radicals and improving the survival of HT22 cells against the reactive oxygen species-mediated cytotoxicity in vitro but also significantly attenuated the ischemia/reperfusion-induced oxidative stress in ischemic rat brains. Results from transient middle cerebral artery occlusion and permanent middle cerebral artery occlusion model, indicated that 3d could significantly reduce infarct size, improve neurobehavioral deficits, and prominently decrease attenuation of cerebral damage. Most importantly, 3d possessed a very high absolute bioavailability and was rapidly distributed in brain tissue to keep high plasma drug concentration for the treatment of ischemic strokes. In conclusion, our findings suggest that 3-alkyl-2,3-dihydro-1H-isoindol-1-ones, a novel series of compounds, might be candidate drugs for the treatment of acute ischemic strokes, and 3d may be a promising therapeutic agent for the primary and secondary prevention of ischemic stroke.