(E,R)-N-(4-methylpentan-2-ylidene)-2-methylpropane-2-sulfinamide | 220263-62-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 亚磺酸及其衍生物
• 英文名称: (E,R)-N-(4-methylpentan-2-ylidene)-2-methylpropane-2-sulfinamide
• 英文别名: (R)-2-methyl-N-[(2E)-1,3-dimethylbutanylidene]-2-propanesulfinamide；(R)-2-methyl-N-[(2E)-1,3-dimethylbutylene]-2-propanesulfinamide；(NE,R)-2-methyl-N-(4-methylpentan-2-ylidene)propane-2-sulfinamide
• CAS: 220263-62-7
• 化学式: C₁₀H₂₁NOS
• 分子量: 203.349
• InChiKey: BPMCPPXULCUUSE-YGNAEDSMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  48.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E,R)-N-(4-methylpentan-2-ylidene)-2-methylpropane-2-sulfinamide 在 盐酸 、 L-Selectride 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 4.0h， 生成 (2S)-4-methyl-2-pentanamine hydrochloride
  参考文献：
  名称：

  [EN] 3-AZABICYCLO(3.1.0)HEXANE DERIVATIVES HAVING KDM5 INHIBITORY ACTIVITY AND USE THEREOF
  [FR] DÉRIVÉS DE 3-AZABICYCLO(3.1.0)HEXANE PRÉSENTANT UNE ACTIVITÉ INHIBITRICE DE KDM5 ET LEUR UTILISATION

  摘要：

  本发明提供了KDM5抑制剂。本文所披露的化合物由一般式(I)表示：其中所有符号的含义与规范中描述的定义相同；或其盐可用作癌症、亨廷顿病、阿尔茨海默病等的预防和/或治疗剂。

  公开号：

  WO2021223699A1
• 作为产物：
  描述：

  4-甲基-2-戊酮 、 (R)-(+)-叔丁基亚磺酰胺 在 titanium(IV) tetraethanolate 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以44.332%的产率得到(E,R)-N-(4-methylpentan-2-ylidene)-2-methylpropane-2-sulfinamide
  参考文献：
  名称：

  [EN] 3-AZABICYCLO(3.1.0)HEXANE DERIVATIVES HAVING KDM5 INHIBITORY ACTIVITY AND USE THEREOF
  [FR] DÉRIVÉS DE 3-AZABICYCLO(3.1.0)HEXANE PRÉSENTANT UNE ACTIVITÉ INHIBITRICE DE KDM5 ET LEUR UTILISATION

  摘要：

  本发明提供了KDM5抑制剂。本文所披露的化合物由一般式(I)表示：其中所有符号的含义与规范中描述的定义相同；或其盐可用作癌症、亨廷顿病、阿尔茨海默病等的预防和/或治疗剂。

  公开号：

  WO2021223699A1

文献信息

• Asymmetric synthesis of pre-protected α,α-disubstituted amino acids from tert-butanesulfinyl ketimines
  作者：George Borg、Masao Chino、Jonathan A Ellman

  DOI：10.1016/s0040-4039(00)02300-5

  日期：2001.2

  method for the asymmetric synthesis of pre-protected α,α-disubstituted amino acids is described. 5-Methylfuryllithium is added into sulfinyl ketimines 1 in the presence of AlMe3 to afford the sulfinamides 2 in 75–97% yields and with diastereoselectivities ranging from 75:25 to 99:1. Subsequent oxidation with RuCl3/NaIO4 affords tert-butanesulfonyl (Bus)-protected α,α-disubstituted amino acids 3 in 62–69%

  描述了一种不对称合成预保护的α，α-二取代氨基酸的方法。5- Methylfuryllithium加入到亚硫酮亚胺1中阿尔梅的存在3，得到亚磺酰胺2在75-97％的产率和非对映选择性与范围从75:25至99：1。用的RuCl随后氧化3 /的NaIO 4，得到叔-butanesulfonyl（总线）保护的α，α-二取代的氨基酸3在62-69％的产率。总线保护的氨基酸容易形成酰胺键，此后可以用TfOH / CH 2 Cl 2除去总线基团，得到游离胺。
• Synthesis of Enantiomerically Pure <i>N</i>-<i>tert</i>-Butanesulfinyl Imines (<i>tert</i>-Butanesulfinimines) by the Direct Condensation of <i>tert</i>-Butanesulfinamide with Aldehydes and Ketones
  作者：Guangcheng Liu、Derek A. Cogan、Timothy D. Owens、Tony P. Tang、Jonathan A. Ellman

  DOI：10.1021/jo982059i

  日期：1999.2.1

  Experimental details for the first general methods for the one-step preparation of N-tert-butanesulfinyl imines (tert-butanesulfinimines) (2) from aldehydes and ketones is described. To effect the condensations of tert-butanesulfinamide (1) with aldehydes, the Lewis acidic dehydrating agents MgSO4, CuSO4, or Ti(OEt)(4) are employed. Aldehyde condensations mediated by MgSO4 proceed in high yields (84-96%) when an excess of aldehyde is used. In contrast, only a slight excess of aldehyde (1.1 equiv) relative to tert-butanesulfinamide provides sulfinimines in high yields when the more Lewis acidic dehydrating agent CuSO4 is used. The CuSO4-mediated procedure is effective for a wide range of aldehydes, including sterically demanding aldehydes, such as isobutyraldehyde (90%), and electron-rich aldehydes, such as p-anisaldehyde (81%). The still more Lewis acidic Ti(OEt)(4) and Ti(O-i-Pr)(4) also afford N-tert-butanesulfinyl aldimines from especially unreactive aldehydes, such as pivaldehyde (82%). In addition, Ti(OEt)(4) is effective for the condensation of I with ketones to afford a wide range of N-tert-butanesulfinyl ketimines in good yields (77-91%). For sulfinyl ketimines derived from methyl or n-alkyl phenyl ketones and methyl or n-alkyl isopropyl ketones, only the E isomer is detected by H-1 and C-13 NMR in CDCl3. For those cases where the difference in steric demand about the imine is very small, such as for 2-hexanone, high E/Z ratios are still observed (5:1).
• One-Pot Asymmetric Synthesis of Either Diastereomer of <i>tert</i>-Butanesulfinyl-protected Amines from Ketones
  作者：Jessica Tanuwidjaja、Hillary M. Peltier、Jonathan A. Ellman

  DOI：10.1021/jo0616512

  日期：2007.1.1

  [GRAPHIC]A one-pot method for the asymmetric synthesis of tert-butanesulfinyl-protected amines is described. Condensation of aryl alkyl and dialkyl ketones with tert-butanesulfinamide followed by in situ reduction with the appropriate reagent provides either diastereomer of the sulfinamide products in good yields and with diastereomeric ratios of up to 99:1.
• Asymmetric Synthesis of α,α-Dibranched Amines by the Trimethylaluminum-Mediated 1,2-Addition of Organolithiums to <i>tert</i>-Butanesulfinyl Ketimines
  作者：Derek A. Cogan、Jonathan A. Ellman

  DOI：10.1021/ja983217q

  日期：1999.1.1