(R)-3-(4-methoxyphenyl)isoindolin-1-one | 126186-81-0

• 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: (R)-3-(4-methoxyphenyl)isoindolin-1-one
• 英文别名: (3R)-3-(4-methoxyphenyl)-2,3-dihydroisoindol-1-one
• CAS: 126186-81-0
• 化学式: C₁₅H₁₃NO₂
• 分子量: 239.274
• InChiKey: JPDCTZYCUZRESY-CQSZACIVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (R)-2-((S)-2-Methoxymethylpyrrolidin-1-yl)-3-(4-methoxyphenyl)-2,3-dihydro-1H-isoindol-1-one 在 水 、 magnesium monoperoxyphthalate hexahydrate 作用下， 以 甲醇 为溶剂， 以91%的产率得到(R)-3-(4-methoxyphenyl)isoindolin-1-one
  参考文献：
  名称：

  A conceptually new approach to the asymmetric synthesis of 3-aryl and alkyl poly-substituted isoindolinones

  摘要：

  A conceptually new and efficient asymmetric synthesis of C-3 arylated or alkylated poly-substituted iso-indolinones is reported. The key step is the diastereoselective reduction of an N-acylhydrazonium species derived from the previously assembled corresponding hydroxyl derivative hearing the (S)-2-methoxymethylpyrrolidine (SMP) auxiliary. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.11.021

文献信息

• Approach to Chiral 1-Substituted Isoquinolone and 3-Substituted Isoindolin-1-one by Addition–Cyclization Process
  作者：Wen Zhou、Yan-Xue Zhang、Xiao-Di Nie、Chang-Mei Si、Xun Sun、Bang-Guo Wei

  DOI：10.1021/acs.joc.8b01282

  日期：2018.9.7

  An approach to access 1-substituted isoquinolones has been developed through the addition–cyclization of imines with Grignard reagents in the presence of 2,2′-dipyridyl. A number of substituted aromatic magnesium reagents were amenable to this process, and the desired products were obtained with excellent yields and outstanding diastereoselectivities (dr > 99:1). The utility of this convenient approach

  通过在2，2'-联吡啶存在下，用格氏试剂对亚胺进行加成环化反应，已经开发了一种获得1-取代异喹诺酮的方法。许多取代的芳族镁试剂都适用于此过程，并以优异的收率和出色的非对映选择性（dr > 99：1）获得了所需的产物。这种便利方法的实用性通过（S）-cryptostyline II的形式合成得到证明。此外，使用格氏试剂一锅加成-环化-亚胺脱保护，发现N-甲基吗啉（NMM）是形成3取代异吲哚啉-1-酮的有效添加剂。
• Asymmetric hydrogenolysis of racemic 3-substitued-3-hydroxy-isoindolin-1-ones employing SPINOL-derived chiral phosphoric acid
  作者：Yiliang Zhang、Li He、Lei Shi

  DOI：10.1016/j.tetlet.2018.03.030

  日期：2018.4

  The asymmetric hydrogenolysis of racemic 3-substitued-3-hydroxyisoindolin-1-ones has been developed employing SPINOL-derived phosphoric acid and a high steric demand Hantzsch ester as the hydrogen source. The corresponding products are obtained in good yields and up to 93% enantioselectivities.

  外消旋的3-取代的3-羟基异吲哚啉-1-酮的不对称氢解反应是利用SPINOL衍生的磷酸和高空间需求量的汉茨酯作为氢源而开发的。以高收率和高达93％的对映选择性获得相应的产物。
• Ir(I)-catalyzed enantioselective hydrogenolysis of 3-aryl-3-hydroxyisoindolin-1-ones
  作者：Chen Ge、Ren-Xiao Liang、Ren-Rong Liu、Bin Xiang、Yi-Xia Jia

  DOI：10.1016/j.tetlet.2016.11.111

  日期：2017.1

  An enantioselective hydrogenolysis of 3-aryl-3-hydroxyisoindolin-1-ones under H2 has been developed by using Ir(I)/(R)-MeO-Biphep complex as a catalyst. Cyclic diaryl methylamides were obtained in moderate to excellent yields and up to 92% ee.

  通过使用Ir（I）/（R）-MeO-Biphep配合物作为催化剂，开发了H 2下3-芳基-3-羟基异吲哚啉-1-酮的对映选择性氢解反应。以中等至优异的产率和高达92％的ee获得环状二芳基甲基酰胺。
• Cobalt‐Catalyzed Enantioselective C−H Carbonylation towards Chiral Isoindolinones
  作者：Ming‐Ya Teng、Yong‐Jie Wu、Jia‐Hao Chen、Fan‐Rui Huang、De‐Yang Liu、Qi‐Jun Yao、Bing‐Feng Shi

  DOI：10.1002/anie.202318803

  日期：2024.3.4

  Transition metal‐catalyzed enantioselective C−H carbonylation with carbon monoxide, an essential and easily available C1 feedstock, remains challenging. Here, we disclosed an unprecedented enantioselective C−H carbonylation catalyzed by inexpensive and readily available cobalt(II) salt. The reactions proceed efficiently through desymmetrization, kinetic resolution, and parallel kinetic resolution, affording a broad range of chiral isoindolinones in good yields with excellent enantioselectivities (up to 92 % yield and 99 % ee). The synthetic potential of this method was demonstrated by asymmetric synthesis of biological active compounds, such as (S)‐PD172938 and (S)‐Pazinaclone. The resulting chiral isoindolinones also serve as chiral ligands in cobalt‐catalyzed enantioselective C−H annulation with alkynes to construct phosphorus stereocenter.

  摘要过渡金属催化的对映体选择性C-H羰基化反应与一氧化碳--一种重要且容易获得的C1原料--仍然具有挑战性。在此，我们揭示了一种前所未有的由廉价易得的钴（II）盐催化的对映体选择性 C-H 羰基化反应。反应通过非对称化、动力学解析和平行动力学解析高效地进行，以良好的产率和优异的对映选择性（高达 92% 的产率和 99% 的ee）获得了多种手性异吲哚啉酮。通过不对称合成生物活性化合物，如(S)-PD172938 和 (S)-Pazinaclone，证明了该方法的合成潜力。所得手性异吲哚啉酮还可作为手性配体，在钴催化下与炔烃进行对映选择性 C-H 环化反应，构建磷立体中心。
• Enantioconvergent Cu-Catalyzed Intramolecular C–C Coupling at Boron-Bound C(sp³) Atoms of α-Aminoalkylboronates Using a <i>C</i>₁-Symmetrical 2,2′-Bipyridyl Ligand Attached to a Helically Chiral Macromolecular Scaffold
  作者：Yukako Yoshinaga、Takeshi Yamamoto、Michinori Suginome

  DOI：10.1021/jacs.0c09080

  日期：2020.10.28

  Enantioconvergent intramolecular coupling of alpha-(2-bromobenzoylamino)benzylboronic esters was achieved using a copper catalyst having helically chiral macromolecular bipyridyl ligand, PQXbpy. Racemic alpha-(2-bromobenzoylamino)benzylboronic esters were converted into (R)-configured 3-arylisoindolinones with high enantiopurity using right-handed helical PQXbpy as a chiral ligand in a toluene/CHCI3 mixed solvent. When enantiopure (R)- and (S)-configured boronates were separately reacted under the same reaction conditions, both afforded (R)-configured products through formal stereoinvertive and stereoretentive processes, respectively. From these results, a mechanism involving deracemization of organocopper intermediates in the presence of PQXbpy is assumed. PQXbpy switched its helical sense to left-handed when a toluene/1,1,2-trichloroethane mixed solvent was used, resulting in the formation of the corresponding (S)-products from the racemic starting material.