(R)-(-)-1-cyclopropyl-but-3-en-1-ol | 1132094-35-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (R)-(-)-1-cyclopropyl-but-3-en-1-ol
• 英文别名: (R)-1-cyclopropyl-but-3-en-1-ol；(1R)-1-cyclopropylbut-3-en-1-ol
• CAS: 1132094-35-9
• 化学式: C₇H₁₂O
• 分子量: 112.172
• InChiKey: XFQJRACBVRDQSM-SSDOTTSWSA-N

物化性质

• 沸点：
  167.2±9.0 °C(predicted)
• 密度：
  0.980±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  8
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (R)-(-)-1-cyclopropyl-but-3-en-1-ol 、 (R)-methoxytrifluoromethylphenylacetyl chloride 在 吡啶 、 4-二甲氨基吡啶 作用下， 生成
  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：

  tert-butyl-((R)-1-cyclopropyl-but-3-enyloxy)-dimethyl-silane 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 以87%的产率得到(R)-(-)-1-cyclopropyl-but-3-en-1-ol
  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

文献信息

• Catalytic Asymmetric Allylation of Aliphatic Aldehydes by Chiral Bipyridine <i>N</i>,<i>N</i>′-Dioxides
  作者：Martin Kotora、Radim Hrdina、Thomas Boyd、Irena Valterová、Jana Hodačová

  DOI：10.1055/s-0028-1087412

  日期：——

  A new class of axially chiral bipyridine N,N¢-oxides with bis(tetrahydroisoquinoline) framework were tested as catalysts in the reaction of aliphatic aldehydes with allyl(trichloro)silane to af- ford homoallylic alcohols. The course of the reaction, that is, the catalytic activity as well as enantioselectivity, is strongly dependent on the solvent used. The products were obtained in good yields and

  测试了一类新的具有双（四氢异喹啉）骨架的轴向手性联吡啶 N,N- 氧化物作为脂肪醛与烯丙基（三氯）硅烷反应生成均烯丙醇的催化剂。反应过程，即催化活性和对映选择性，强烈依赖于所用的溶剂。以良好的收率获得了产物，在氯仿中的 ee 高达 68%。