(R)-3-p-chlorophenyl-2,3-dihydro-1H-isoindolin-1-one | 1329993-61-4

• 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: (R)-3-p-chlorophenyl-2,3-dihydro-1H-isoindolin-1-one
• 英文别名: 3-(4-chlorophenyl)isoindolinone；(3R)-3-(4-chlorophenyl)-2,3-dihydroisoindol-1-one
• CAS: 1329993-61-4
• 化学式: C₁₄H₁₀ClNO
• 分子量: 243.692
• InChiKey: OMUHBVDRMKRVLW-CYBMUJFWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 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：

  氯噻酮杂质J(EP) 在 (11aS)-3,7-di-9-anthracenyl-10,11,12,13-tetrahydro-5-hydroxy-5-oxide diindeno[7,1de:10,70-fg][1,3,2] dioxaphosphocin 、 2,6-二甲基-1,4-二氢吡啶-3,5-二甲酸二叔丁酯 作用下， 以 甲苯 为溶剂， 以94%的产率得到(R)-3-p-chlorophenyl-2,3-dihydro-1H-isoindolin-1-one
  参考文献：
  名称：

  SPINOL衍生的手性磷酸消旋3-取代-3-羟基-异吲哚啉-1-酮的不对称氢解

  摘要：

  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。

  DOI：

  10.1016/j.tetlet.2018.03.030

文献信息

• Stereoselective synthesis of isoindolinones and tert -butyl sulfoxides
  作者：Robert Kawęcki、Wojciech Stańczyk、Agnieszka Jaglińska

  DOI：10.1016/j.tet.2017.12.035

  日期：2018.2

  A reaction of Grignard reagents with an optically pure N-sulfinylimine derived from methyl 2-formylbenzoate yields enantioenriched isoindolinones and tert-butyl sulfoxides. The products are formed by the addition of the nucleophile to N-sulfinylimine followed by cyclization to form N-tert-butylsulfinylisoindolinone, which readily undergoes substitution with a second equivalent of Grignard reagent.

  格氏试剂与衍生自2-甲酰基苯甲酸甲酯的光学纯的N-亚磺酰亚胺反应，得到对映体富集的异吲哚啉酮和叔丁基亚砜。该产品通过加入亲核试剂，以形成Ñ -sulfinylimine随后环化，以形成ñ -叔-butylsulfinylisoindolinone，这容易经历取代与格氏试剂的第二等效。该反应可以在二氯甲烷中在室温或升高的温度下进行，而没有任何立体选择性的损失。还研究了格氏试剂以外的亲核试剂的使用。
• Stereoinvertive C–C Bond Formation at the Boron‐Bound Stereogenic Centers through Copper‐Bipyridine‐Catalyzed Intramolecular Coupling of α‐Aminobenzylboronic Esters
  作者：Yukako Yoshinaga、Takeshi Yamamoto、Michinori Suginome

  DOI：10.1002/anie.201914864

  日期：2020.4.27

  Enantiospecific intramolecular Suzuki-Miyaura-type coupling with α-(2-halobenzoylamino)benzylboronic esters to give 3-substituted isoindolinones is achieved by using copper catalysts with 2,2'-bipyridine-based achiral ligands. Enantioenriched α-aminobenzylboron reactants bearing a hydrogen atom at the boron-bound stereogenic carbons undergo stereoinvertive coupling in the presence of a 6-phenyl-2,2'-bipyridine

  通过使用具有2,2'-联吡啶的非手性配体的铜催化剂，可以实现与α-（2-卤代苯甲酰基氨基）苄基硼酸酯的对映体分子内Suzuki-Miyaura型偶联，生成3-取代的异吲哚啉酮。在具有高对映体特异性的6-苯基-2,2'-联吡啶配体的存在下，在硼结合的立体碳上带有氢原子的对映体富集的α-氨基苄基硼反应物进行立体反转偶联。在存在简单的2,2'-联吡啶作为配体的情况下，带有完全取代的与硼结合的立体成核中心的α-氨基苄基硼酸酯也给出了3,3-二取代的异吲哚啉酮，具有立体定向的立体化学转化作用。
• 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。
• 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.
• Chiral phosphoric acid catalyzed asymmetric hydrogenolysis of racemic 3-aryl-3-hydroxyisoindolin-1-ones
  作者：Jian-Qing Zhou、Wei-Jian Sheng、Jian-Hong Jia、Qing Ye、Jian-Rong Gao、Yi-Xia Jia

  DOI：10.1016/j.tetlet.2013.03.138

  日期：2013.6

  The enantioselective hydrogenolysis of racemic 3-aryl-3-hydroxyisoindolin-1-ones catalyzed by BINOL-derived chiral phosphoric acid with benzothiazoline as the hydride source is described. The corresponding cyclic diaryl methylamines are obtained in good to excellent yields and up to 91% enantioselectivities. (C) 2013 Elsevier Ltd. All rights reserved.