(S)-1-cyclopropyl-ethane-1,2-diol | 615251-45-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (S)-1-cyclopropyl-ethane-1,2-diol
• 英文别名: (1S)-1-cyclopropyl-1,2-dihydroxyethane；(1S)-1-Cyclopropyl-1,2-ethanediol；(1S)-1-cyclopropylethane-1,2-diol
• CAS: 615251-45-1
• 化学式: C₅H₁₀O₂
• 分子量: 102.133
• InChiKey: BGVZHHMFIIQQEX-RXMQYKEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  7
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-1-cyclopropyl-ethane-1,2-diol 、 对甲苯磺酰氯 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 以59%的产率得到toluene-4-sulfonic acid (S)-2-cyclopropyl-2-hydroxy-ethyl ester
  参考文献：
  名称：

  Enantioselective Synthesis of Iclaprim Enantiomers―A Versatile Approach to 2-Substituted Chiral Chromenes

  摘要：

  Both enantiomers of the DHFR inhibitor iclaprim (R)-1 and (5)-1 were synthesized from the cyclopropyl homoallyl alcohols (R)-6 and (S)-6. respectively. As key steps these transformations include a Mitsunobu reaction and the formation of the diaminopyrimidine unit prior to a novel cyclization procedure to obtain the desired chromene heterocycle. The moderate enantioselectivity of the products (R)-1 and OH is related to the Mitsunobu reaction, which unfortunately did not proceed with complete inversion or configuration.

  DOI：

  10.1021/jo100566c
• 作为产物：
  描述：

  乙烯基环丙烷 在 potassium osmate(VI) 、 2,5-diphenyl-4,6-pyrimidynediyl hydrochininine diether 、 potassium carbonate 、 potassium hexacyanoferrate(III) 、 sodium sulfite 作用下， 以 水 、 叔丁醇 为溶剂， 反应 25.25h， 以64%的产率得到
  参考文献：
  名称：

  [EN] PREPARATION OF 24 ALKYL ANALOGS OF CHOLECALCIFEROL AND NON-RACEMIC COMPOUNDS
  [FR] PREPARATION D'ANALOGUES ALKYL-24 DE CHOLECALCIFEROL ET DE COMPOSES NON RACEMIQUES

  摘要：

  公开号：

  WO2003087048A3

文献信息

• [EN] PREPARATION OF 24 ALKYL ANALOGS OF CHOLECALCIFEROL AND NON-RACEMIC COMPOUNDS<br/>[FR] PREPARATION D'ANALOGUES ALKYL-24 DE CHOLECALCIFEROL ET DE COMPOSES NON RACEMIQUES
  申请人：——

  公开号：WO2003087048A3

  公开（公告）日：2004-03-18
• Enantioselective Synthesis of Iclaprim Enantiomers―A Versatile Approach to 2-Substituted Chiral Chromenes
  作者：Chouaib Tahtaoui、Arnold Demailly、Carole Guidemann、Cécile Joyeux、Peter Schneider

  DOI：10.1021/jo100566c

  日期：2010.6.4

  Both enantiomers of the DHFR inhibitor iclaprim (R)-1 and (5)-1 were synthesized from the cyclopropyl homoallyl alcohols (R)-6 and (S)-6. respectively. As key steps these transformations include a Mitsunobu reaction and the formation of the diaminopyrimidine unit prior to a novel cyclization procedure to obtain the desired chromene heterocycle. The moderate enantioselectivity of the products (R)-1 and OH is related to the Mitsunobu reaction, which unfortunately did not proceed with complete inversion or configuration.