1R,2S-2-methyl-1-phenylethynylcyclopropanol | 208516-67-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1R,2S-2-methyl-1-phenylethynylcyclopropanol
• 英文别名: (1R,2S)-2-methyl-1-(2-phenylethynyl)cyclopropan-1-ol
• CAS: 208516-67-0
• 化学式: C₁₂H₁₂O
• 分子量: 172.227
• InChiKey: TWVUTGIFYRJTAM-CMPLNLGQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 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：

  1R,2S-2-methyl-1-phenylethynylcyclopropanol 在 1,3-丙二硫醇 、 氢氧化钾 、 lithium aluminium tetrahydride 、 sodium azide 、 15-冠醚-5 、 三乙胺 、 三苯基膦 、 bis(dibenzylideneacetone)-palladium⁽⁰⁾ 作用下， 以 甲醇 、 乙醚 、 叔丁醇 为溶剂， 生成 [(1R,2S)-2-Methyl-1-((E)-styryl)-cyclopropyl]-carbamic acid tert-butyl ester
  参考文献：
  名称：

  Diastereoselective palladium(0)-catalyzed azidation of 1-alkenylcyclopropyl esters: asymmetric synthesis of (−)-(1R,2S)-norcoronamic acid

  摘要：

  Palladium(0)-catalyzed azidation of (1R,2S)-1-(1-alkenyl)2-methylcyclopropyl esters 10a,b proceeds with complete retention of configuration to provide, after reduction of the azide and oxidative cleavage of the allylic double bond, the (1R,2S)-norcoronamic acid 22 (>99% e.e.). (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(98)00107-4
• 作为产物：
  描述：

  lithium phenylacetylide 、 (S)-1-Ethoxy-2-methyl-cyclopropanol 在 乙基溴化镁 作用下， 生成 (1R^*,2R^*)-2-methyl-1-phenylethynylcyclopropanol 、 1R,2S-2-methyl-1-phenylethynylcyclopropanol
  参考文献：
  名称：

  Diastereoselective palladium(0)-catalyzed azidation of 1-alkenylcyclopropyl esters: asymmetric synthesis of (−)-(1R,2S)-norcoronamic acid

  摘要：

  Palladium(0)-catalyzed azidation of (1R,2S)-1-(1-alkenyl)2-methylcyclopropyl esters 10a,b proceeds with complete retention of configuration to provide, after reduction of the azide and oxidative cleavage of the allylic double bond, the (1R,2S)-norcoronamic acid 22 (>99% e.e.). (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(98)00107-4

文献信息

• Rearrangement of 1-(1-Alkynyl)cyclopropanols to 2-Cyclopentenones via Their Hexacarbonyldicobalt Complexes. A New Use of Alkyne−Co₂(CO)₆ Complexes in Organic Synthesis
  作者：Nobuharu Iwasawa、Takeshi Matsuo、Mari Iwamoto、Taketo Ikeno

  DOI：10.1021/ja9734004

  日期：1998.4.1

  protective group of the substrates. This rearrangement was successfully applied to cyclopentenone annulation reactions onto cycloalkenes. An efficient synthesis of alkynyl-substituted bicyclo[n.1.0]alkanol derivatives from the corresponding cycloalkenes according to Danheiser's protocol was developed, and bicyclic cyclopentenones were obtained in moderate to good yield by applying to these the cobalt-mediated

  1-(1-炔基) 环丙醇向 2-环戊烯-1-酮的新重排是在其炔基部分与八羰基二钴 (Co2(CO8)) 络合后进行的。1-(1-炔基) 环丙醇在其炔烃末端具有广泛的取代基，以良好的产率重排为相应的 3-取代的 2-环戊烯-1-酮。In case of the reactions of 1-alkynylcyclopropanols with an alkyl substituent on the cyclopropane ring, either 4-substituted or 5-substituted 2-cyclopenten-1-ones could be selectively obtained by appropriate choice of stereochemistry and protective group of the substrates. 这种重排成功地应用于环戊烯酮环化成环烯烃的反应。根据