(R)-2-phenylsuccinimide | 114531-20-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: (R)-2-phenylsuccinimide
• 英文别名: (R)-3-phenyl-2,5-pyrrolidinedione；(3R)-3-phenylpyrrolidine-2,5-dione
• CAS: 114531-20-3
• 化学式: C₁₀H₉NO₂
• 分子量: 175.187
• InChiKey: FVSWNQYFMNGPLF-MRVPVSSYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  46.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (R)-2-phenylsuccininic anhydride 在 氯化亚砜 、 氨 作用下， 生成 (R)-2-phenylsuccinimide
  参考文献：
  名称：

  Polonski, Tadeusz, Journal of the Chemical Society. Perkin transactions I, 1988, p. 629 - 638

  摘要：

  DOI：

文献信息

• Highly Enantioselective Synthesis of Chiral Succinimides via Rh/Bisphosphine-Thiourea-Catalyzed Asymmetric Hydrogenation
  作者：Zhengyu Han、Pan Li、Zongpeng Zhang、Caiyou Chen、Qian Wang、Xiu-Qin Dong、Xumu Zhang

  DOI：10.1021/acscatal.6b01615

  日期：2016.9.2

  We have successfully developed a highly enantioselective hydrogenation of various 3-aryl and 3-methyl maleinimides to access enantiomerically pure 3-substituted succinimides catalyzed by Rh/bisphosphine-thiourea (ZhaoPhos). This efficient catalytic system furnished the desired 3-substituted succinimide products with high yields and enantioselectivities (up to 99% yield, full conversions, almost all

  我们已经成功地开发了各种3-芳基和3-甲基马来酰亚胺的高度对映选择性加氢，以得到对映体纯的3-取代的琥珀酰亚胺，其被Rh /双膦-硫脲（ZhaoPhos）催化。这种高效的催化体系为所需的3-取代的琥珀酰亚胺产品提供了高收率和对映选择性（高达99％的收率，完全转化率，几乎所有3-芳基琥珀酰亚胺产品的ee达99％ee，3-甲基琥珀酰亚胺的83％ee） 。我们的催化系统具有很强的底物耐受性和通用性。无论马来酰亚胺的N-取代基是H还是其他保护基，马来酰亚胺都被充分氢化（高达> 99％ee，99％收率）。此外，氢化琥珀酰亚胺产品可轻松用于构建生物活性分子，
• Direct Synthesis of Chiral 3-Arylsuccinimides by Rhodium-Catalyzed Enantioselective Conjugate Addition of Arylboronic Acids to Maleimides
  作者：Balraj Gopula、Shu-Han Yang、Ting-Shen Kuo、Jen-Chieh Hsieh、Ping-Yu Wu、Julian P. Henschke、Hsyueh-Liang Wu

  DOI：10.1002/chem.201501059

  日期：2015.7.27

  ligands L1–L10 were utilized in the enantioselective 1,4‐addition reaction of arylboronic acids to N‐substituted maleimides. In the presence of 2.5 mol % of RhI/L2, enantioenriched conjugate addition adducts were isolated in 72–99 % yields with 86–98 % ee. This protocol offers a convenient method to access a variety of 3‐arylsuccinimides in a highly enantioselective manner. Maleimides with readily cleavable

  包含2,5-二芳基取代的双环[2.2.1]二烯配体L1 - L10的手性铑催化剂用于芳基硼酸与N-取代的马来酰亚胺的1,4-加成对映选择性反应。在存在2.5 mol％Rh I / L2的情况下，分离出对映体富集的共轭加合物，收率为72–99％，ee为86–98％  。该协议提供了一种方便的方法，可以以高对映选择性的方式访问各种3-芳基琥珀酰亚胺。具有易于裂解的N-保护基的马来酰亚胺被耐受，从而能够合成有用的合成中间体。吡咯烷4中，生物活性化合物和吡咯烷5，一个ENT -precursor到HSD-1抑制剂，合成以证明该方法的效用。
• [EN] SUBSTITUTED CYCLIC HYDROXAMATES AS INHIBITORS OF MATRIX METALLOPROTEINASES<br/>[FR] INHIBITEURS DE METALLOPROTEASES MATRICES A BASE D'HYDROXAMATES CYCLIQUES SUBSTITUES
  申请人：INCYTE CORP

  公开号：WO2005037826A1

  公开（公告）日：2005-04-28

  The present invention provides compounds of the formula I: its enantiomers, diastereomers, racemic mixtures thereof, prodrugs, crystalline forms, non-crystalline forms, amorphous forms thereof, solvates thereof, metabolites thereof, and pharmaceutically acceptable salts, wherein the ring A substituent groups are fully defined in the following disclosure. The compounds of formula I are inhibitors of metalloproteases such as matrix metalloproteases and sheddases, and are useful in treating diseases such as rheumatoid arthritis, psoriasis, neoplastic diseases, allergies and all those diseases wherein inhibition of MMPs is desirable.

  本发明提供了公式I的化合物：其对映异构体，二对映异构体，混合物，前药，结晶形式，非晶形式，无定形形式，溶剂化物，代谢物和药学上可接受的盐，其中环A取代基在以下披露中被完全定义。公式I的化合物是金属蛋白酶抑制剂，如基质金属蛋白酶和剪切酶的抑制剂，并且在治疗风湿性关节炎，牛皮癣，肿瘤性疾病，过敏和所有需要MMPs抑制的疾病中有用。
• Substituted cyclic hydroxamates as lnhibitors of matrix metalloproteinases
  申请人：Li Yun Long

  公开号：US20080167288A1

  公开（公告）日：2008-07-10

  The present invention provides compounds of the formula: its enantiomers, diastereomers, racemic mixtures thereof, prodrugs, crystalline forms, non-crystalline forms, amorphous forms thereof, solvates thereof, metabolites thereof, and pharmaceutically acceptable salts, wherein the ring A substituent groups are fully defined in the following disclosure. The compounds of formula are inhibitors of metalloproteases such as matrix metalloproteases and sheddases, and are useful in treating diseases such as rheumatoid arthritis, psoriasis, neoplastic diseases, allergies and all those diseases wherein inhibition of MMPs is desirable.

  本发明提供了公式的化合物：其对映异构体、非对映异构体、混合物、前药、晶体形式、非晶体形式、无定形形式、溶剂化物、代谢物和药学上可接受的盐，其中环A的取代基在下面的披露中被完全定义。公式化合物是金属蛋白酶抑制剂，如基质金属蛋白酶和脱落酶，可用于治疗风湿性关节炎、银屑病、肿瘤性疾病、过敏和所有需要抑制MMP的疾病。
• SUBSTITUTED CYCLIC HYDROXAMATES AS INHIBITORS OF MATRIX METALLOPROTEINASES
  申请人：Li Yun-Long

  公开号：US20110224189A1

  公开（公告）日：2011-09-15

  The present invention provides compounds of the formula: its enantiomers, diastereomers, racemic mixtures thereof, prodrugs, crystalline forms, non-crystalline forms, amorphous forms thereof, solvates thereof, metabolites thereof, and pharmaceutically acceptable salts, wherein the ring A substituent groups are fully defined in the following disclosure. The compounds of formula are inhibitors of metalloproteases such as matrix metalloproteases and sheddases, and are useful in treating diseases such as rheumatoid arthritis, psoriasis, neoplastic diseases, allergies and all those diseases wherein inhibition of MMPs is desirable.

  本发明提供了化合物的公式：其对映异构体，对映体混合物，前药，晶体形式，非晶体形式，无定形形式，其溶剂化物，代谢产物以及药学上可接受的盐，其中环A的取代基在以下披露中完全定义。公式化合物是金属蛋白酶抑制剂，例如基质金属蛋白酶和剪切酶，并且在治疗风湿性关节炎，牛皮癣，肿瘤性疾病，过敏和所有需要抑制MMP的疾病中有用。