[(2R)-2-(1,3-dioxoisoindol-2-yl)propyl] trifluoromethanesulfonate | 171557-15-6

• 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: [(2R)-2-(1,3-dioxoisoindol-2-yl)propyl] trifluoromethanesulfonate
• CAS: 171557-15-6
• 化学式: C₁₂H₁₀F₃NO₅S
• 分子量: 337.276
• InChiKey: JNLNCGFLPFDIMW-SSDOTTSWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  89.1
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  [(2R)-2-(1,3-dioxoisoindol-2-yl)propyl] trifluoromethanesulfonate 在 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 52.0h， 生成 [1-[(R)-2-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-propyl]-3-((R)-1-phenyl-ethyl)-ureido]-acetic acid tert-butyl ester
  参考文献：
  名称：

  Stereocontrolled Synthesis of DTPA Analogs Branched in the Ethylene Unit

  摘要：

  Stereochemically controlled synthesis of diethylenetriaminepentaacetic acid (DTPA) analogues substituted on the ethylene backbones with methyl groups, the chiral center a to the terminal nitrogen being derived from (S)- or (R)-alanine, has been achieved. The key intermediate (S)-propylenediaminetriacetic acid triester was synthesized via selective detosylation of the alkylation product derived from (S)-alanine and tert-butyl glycinate. Attaching the remaining modified alanine (or glycine) fragment through acyl coupling and then selective reduction of the amide followed by hydrolysis of the esters afforded the substituted DTPA analogues. Ester differentiation has been accomplished through alkylation rather than acylation of the (S)-propylenediaminetriacetic acid triester. A byproduct from this alkylation is the oxazoloisoindole formed by internal alkylation of the oxygen of the phthaloyl protecting group. Phthaloyl deprotection followed by dialkylation afforded the ester-differentiated (S,S)-dipropylenetriaminepentaacetic esters. The enantiomeric purity of the chiral intermediates (S)-alaninol and (S)-propylenediamines were determined by HPLC using epimeric standards.

  DOI：

  10.1021/jo00126a059
• 作为产物：
  描述：

  三氟甲磺酸酐 、 (R)-(-)-2-酞酰亚胺基-1-丙醇 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.75h， 以92%的产率得到[(2R)-2-(1,3-dioxoisoindol-2-yl)propyl] trifluoromethanesulfonate
  参考文献：
  名称：

  Stereocontrolled Synthesis of DTPA Analogs Branched in the Ethylene Unit

  摘要：

  Stereochemically controlled synthesis of diethylenetriaminepentaacetic acid (DTPA) analogues substituted on the ethylene backbones with methyl groups, the chiral center a to the terminal nitrogen being derived from (S)- or (R)-alanine, has been achieved. The key intermediate (S)-propylenediaminetriacetic acid triester was synthesized via selective detosylation of the alkylation product derived from (S)-alanine and tert-butyl glycinate. Attaching the remaining modified alanine (or glycine) fragment through acyl coupling and then selective reduction of the amide followed by hydrolysis of the esters afforded the substituted DTPA analogues. Ester differentiation has been accomplished through alkylation rather than acylation of the (S)-propylenediaminetriacetic acid triester. A byproduct from this alkylation is the oxazoloisoindole formed by internal alkylation of the oxygen of the phthaloyl protecting group. Phthaloyl deprotection followed by dialkylation afforded the ester-differentiated (S,S)-dipropylenetriaminepentaacetic esters. The enantiomeric purity of the chiral intermediates (S)-alaninol and (S)-propylenediamines were determined by HPLC using epimeric standards.

  DOI：

  10.1021/jo00126a059

文献信息

• SUBSTITUTED PIPERAZINES AS CB1 ANTAGONISTS
  申请人：Gilbert Eric J.

  公开号：US20100286160A1

  公开（公告）日：2010-11-11

  Compounds of Formula (I): or pharmaceutically acceptable salts, solvates, or esters thereof, are useful in treating diseases or conditions mediated by CB1 receptors, such as metabolic syndrome and obesity, neuroinflammatory disorders, cognitive disorders and psychosis, addiction (e.g., smoking cessation), gastrointestinal disorders, and cardiovascular conditions.
• [EN] SUBSTITUTED PIPERAZINES AS CB1 ANTAGONISTS<br/>[FR] PIPÉRAZINES À SUBSTITUTION SERVANT D'ANTAGONISTES DES RÉCEPTEURS CB1
  申请人：SCHERING CORP

  公开号：WO2009005671A2

  公开（公告）日：2009-01-08

  Compounds of Formula (I): or pharmaceutically acceptable salts, solvates, or esters thereof, are useful in treating diseases or conditions mediated by CB1 receptors, such as metabolic syndrome and obesity, neuroinflammatory disorders, cognitive disorders and psychosis, addiction (e.g., smoking cessation), gastrointestinal disorders, and cardiovascular conditions.
• Stereocontrolled Synthesis of DTPA Analogs Branched in the Ethylene Unit
  作者：Christopher W. Grote、Dong Jin Kim、Henry Rapoport

  DOI：10.1021/jo00126a059

  日期：1995.10

  Stereochemically controlled synthesis of diethylenetriaminepentaacetic acid (DTPA) analogues substituted on the ethylene backbones with methyl groups, the chiral center a to the terminal nitrogen being derived from (S)- or (R)-alanine, has been achieved. The key intermediate (S)-propylenediaminetriacetic acid triester was synthesized via selective detosylation of the alkylation product derived from (S)-alanine and tert-butyl glycinate. Attaching the remaining modified alanine (or glycine) fragment through acyl coupling and then selective reduction of the amide followed by hydrolysis of the esters afforded the substituted DTPA analogues. Ester differentiation has been accomplished through alkylation rather than acylation of the (S)-propylenediaminetriacetic acid triester. A byproduct from this alkylation is the oxazoloisoindole formed by internal alkylation of the oxygen of the phthaloyl protecting group. Phthaloyl deprotection followed by dialkylation afforded the ester-differentiated (S,S)-dipropylenetriaminepentaacetic esters. The enantiomeric purity of the chiral intermediates (S)-alaninol and (S)-propylenediamines were determined by HPLC using epimeric standards.