N-(1-hydroxymethyl-2,2-dimethyl-propyl)-2,2-dimethyl-propanamide | 383149-98-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-(1-hydroxymethyl-2,2-dimethyl-propyl)-2,2-dimethyl-propanamide
• 英文别名: N-[(2S)-1-hydroxy-3,3-dimethylbutan-2-yl]-2,2-dimethylpropanamide
• CAS: 383149-98-2
• 化学式: C₁₁H₂₃NO₂
• 分子量: 201.309
• InChiKey: VKCBCVKQIGVRHX-MRVPVSSYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.91
• 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：

  N-(1-hydroxymethyl-2,2-dimethyl-propyl)-2,2-dimethyl-propanamide 在 三苯基膦 作用下， 生成 (S)-2,4-di-t-butyl-4,5-dihydrooxazole
  参考文献：
  名称：

  [EN] CATALYTICS ASYMMETRIC ACTIVATION OF UNACTIVATED C-H BONDS, AND COMPOUNDS RELATED THERETO
  [FR] ACTIVATION CATALYTIQUE ASYMETRIQUE DE LIAISONS C-H INACTIVEES ET COMPOSES ASSOCIES

  摘要：

  本发明的一个方面部分涉及简单有机底物中未活化C-H键的催化和对映选择性官能团化。本发明提供的化合物和方法允许在C-H活化步骤中控制立体化学，活化含有邻近导向基团的α-氢的底物，并在温和条件下移除导向基团。本发明的另一方面涉及一种过渡金属催化的方法，用于选择性和非对称氧化位于辅助基团β-或Ϝ-位置上的碳。发明的另一个方面涉及通过所述方法形成的对映体富集的底物和对映体富集的产品。在某些实施例中，使用了恶唑啉和恶嗪酮导向基团。此外，Boc保护基团被识别为不需要移除的导向基团。

  公开号：

  WO2006026053A1
• 作为产物：
  描述：

  三甲基乙酸 在 草酰氯 作用下， 生成 N-(1-hydroxymethyl-2,2-dimethyl-propyl)-2,2-dimethyl-propanamide
  参考文献：
  名称：

  钯在温和条件下催化未活化CH键的不对称碘化。

  摘要：

  DOI：

  10.1002/anie.200462884

文献信息

• [EN] CATALYTICS ASYMMETRIC ACTIVATION OF UNACTIVATED C-H BONDS, AND COMPOUNDS RELATED THERETO<br/>[FR] ACTIVATION CATALYTIQUE ASYMETRIQUE DE LIAISONS C-H INACTIVEES ET COMPOSES ASSOCIES
  申请人：UNIV BRANDEIS

  公开号：WO2006026053A1

  公开（公告）日：2006-03-09

  One aspect of the present invention is directed in part to catalytic and stereoselective functionalization of unactivated C-H bonds of simple organic substrates. The compounds and methods provided herein allow one to control the stereochemistry in a C-H activation step, activate substrates containing α-hydrogens next to the directing group, and remove a directing group under mild conditions. One aspect of the present invention relates to a transition-metal-catalyzed method for selective and asymmetric oxidation of carbons located in a β- or Ϝ-position relative to an auxiliary. Another aspect of the invention relates to the enantiomerically-enriched substrates and the enantiomerically-enriched products formed via said method. In certain embodiments, oxazoline and oxazinone directing groups are used. In addition, the Boc protecting group has been identified as a directing group which does not necessitate removal.

  本发明的一个方面部分涉及简单有机底物中未活化C-H键的催化和对映选择性官能团化。本发明提供的化合物和方法允许在C-H活化步骤中控制立体化学，活化含有邻近导向基团的α-氢的底物，并在温和条件下移除导向基团。本发明的另一方面涉及一种过渡金属催化的方法，用于选择性和非对称氧化位于辅助基团β-或Ϝ-位置上的碳。发明的另一个方面涉及通过所述方法形成的对映体富集的底物和对映体富集的产品。在某些实施例中，使用了恶唑啉和恶嗪酮导向基团。此外，Boc保护基团被识别为不需要移除的导向基团。
• Development of a Chiral DMAP Catalyst for the Dynamic Kinetic Resolution of Azole Hemiaminals
  作者：Artis Kinens、Marcis Sejejs、Adam S. Kamlet、David W. Piotrowski、Edwin Vedejs、Edgars Suna

  DOI：10.1021/acs.joc.6b02955

  日期：2017.1.20

  A new catalyst for the dynamic kinetic resolution of azole hemiaminals has been developed using late-stage structural modifications of the tert-leucinol-derived chiral subunit of DMAP species.

  使用DMAP物种的叔亮氨酸衍生的手性亚基的后期结构修饰，开发了用于苯丙胺醛缩甲醛的动力学动力学拆分的新催化剂。
• Aryl, heteroaryl, and heterocyclic pharmaceutical compounds for treatment of medical disorders
  申请人：Achillion Pharmaceuticals, Inc.

  公开号：US11084800B2

  公开（公告）日：2021-08-10

  Complement Factor D inhibitors, pharmaceutical compositions, and uses thereof, as well as processes for their manufacture are provided. The compounds provided include Formula I, Formula II, Formula III, Formula IV, and Formula V, or a pharmaceutically acceptable salt, prodrug, isotopic analog, N-oxide, or isolated isomer thereof, optionally in a pharmaceutically acceptable composition. The inhibitors described herein target Factor D and inhibit or regulate the complement cascade.

  本发明提供了补体因子 D 抑制剂、药物组合物及其用途以及制造工艺。所提供的化合物包括式I、式II、式III、式IV和式V，或其药学上可接受的盐、原药、同位素类似物、N-氧化物或分离异构体，可选药学上可接受的组合物。本文所述的抑制剂以因子 D 为靶点，抑制或调节补体级联。
• Nucleophilic Acyl Substitutions of Anhydrides with Protic Nucleophiles Catalyzed by Amphoteric, Oxomolybdenum Species
  作者：Chien-Tien Chen、Jen-Huang Kuo、Vijay D. Pawar、Yogesh S. Munot、Shieu-Shien Weng、Cheng-Hsiu Ku、Cheng-Yuan Liu

  DOI：10.1021/jo048363v

  日期：2005.2.1

  [GRAPHICS]Among six different group VIb oxometallic species examined, dioxomolybdenum dichloride and oxomolybdenum tetrachloride were the most efficient catalysts to facilitate nucleophilic acyl substitution (NAS) of anhydrides with a myriad array of alcohols, amines, and thiols in high yields and high chemoselectivity. In contrast to the well-recognized redox chemical behaviors associated with oxomolybdenum(VI) species, the catalytic NAS was unprecedented and tolerates virtually all kinds of functional groups. By using benzoic anhydride as a mediator for in situ generation of an incipient mixed anhydride -MoO2Cl2 adduct with a given functional alkanoic acid, one can achieve oleate, dipeptide, diphenylmethyl, N-Fmoc-alpha-amino, pyruvic, and tert-butylthio ester, N-tert-butylamide, and trityl methacrylate syntheses with appropriate protic nucleophiles. The amphoteric character of the Mo=O unit in oxomolybdenum chlorides was found to be responsible for the catalytic NAS profile as supported by a control NAS reaction of using an authentic adduct-MoOCl2(O-2-CBut)(2) between pivalic anhydride and MoO2Cl2 as the catalyst.
• Catalytic Nucleophilic Acyl Substitution of Anhydrides by Amphoteric Vanadyl Triflate
  作者：Chien-Tien Chen、Jen-Huang Kuo、Chun-Hsin Li、N. B. Barhate、Sang-Wen Hon、Tai-Wei Li、Shi-Deh Chao、Chia-Cheng Liu、Ying-Chieh Li、I-Hsin Chang、Jin-Sheng Lin、Chin-Jing Liu、Y-Chen Chou

  DOI：10.1021/ol016684c

  日期：2001.11.1

  [GRAPHICS]Among four vanadyl species examined, vanadyl triflate was the most efficient catalyst to facilitate nucleophilic acyl substitution of anhydrides with a myriad array of alcohols, amines, and thiols in high yields and high chemoselectivity. By using mixed-anhydride technique, one can achieve oleate and peptide syntheses. In marked contrast to common metal triflates, the amphoteric character of the V=O unit in vanadyl species was proven to be responsible for the catalytic profile in this process.