2-methyl-1-(phenylethynyl)cyclopentanol | 154020-87-8

• 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: 2-methyl-1-(phenylethynyl)cyclopentanol
• 英文别名: 2-methyl-1-phenylethynylcyclopentanol；2-methyl-1-(2-phenylethynyl)cyclopentan-1-ol
• CAS: 154020-87-8
• 化学式: C₁₄H₁₆O
• 分子量: 200.28
• InChiKey: DXRMLMZKGWTYSH-UHFFFAOYSA-N

物化性质

• 沸点：
  327.5±25.0 °C(Predicted)
• 密度：
  1.08±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 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：

  2-methyl-1-(phenylethynyl)cyclopentanol 在 对甲苯磺酸 N-碘代丁二酰亚胺 作用下， 以 乙腈 为溶剂， 生成 (2-Methyl-cyclopent-1-enylethynyl)-benzene
  参考文献：
  名称：

  Conversions of phenylalkynylcyclopentanols to α-iodoenones

  摘要：

  N-Iodosuccinimide and catalytic amounts of Koser's reagent react with phenylalkynylcyclopentanols to afford alpha-iodoenones. No ring expansions occur.

  DOI：

  10.1016/s0040-4039(00)61391-6
• 作为产物：
  描述：

  2-甲基环戊酮 、 lithium phenylacetylide 以 四氢呋喃 为溶剂， 以60%的产率得到2-methyl-1-(phenylethynyl)cyclopentanol
  参考文献：
  名称：

  Synthesis of haloenones and aryl or alkyl substituted enones or alkenes

  摘要：

  合成卤代酮和卤代烯烃的替代方法及其用作合成取代或未取代烷基和芳基取代的烯酮和烯烃的起始材料，包括他莫昔芬和他莫昔芬类似物，使用这些卤代酮和卤代烯烃。

  公开号：

  US05446203A1

文献信息

• Hypoiodous acid initiated rearrangement of tertiary propargylic alcohols to α-iodoenones
  作者：Wesley J. Moran、Arantxa Rodríguez

  DOI：10.1039/c2ob26360b

  日期：——

  In the presence of an oxidant, sodium iodide is converted into hypoiodous acid which effects the rearrangement of tertiary propargylic alcohols to α-iodoenones in good yields.

  在氧化剂存在下，碘化钠转化为 次碘酸 从而以高收率将叔炔丙醇重排为α-碘烯。
• Structure of 2-Methyl-1-(phenylethynyl)cyclopentanol and of Its Co2(CO)6 and (C5H5)2Mo2(CO)4 Cluster Complexes Co2(CO)6 as a Conformational Switch
  作者：Krisztina L. Malisza、Luc Girard、Donald W. Hughes、James F. Britten、Michael J. McGlinchey

  DOI：10.1021/om00010a035

  日期：1995.10

  Treatment of 2-methylcyclopentanone with PhC=CMgBr yields 2-methyl-1-(phenylethynyl)cyclopentanol (6'), in which the alkynyl group is axial and cis to the methyl substituent. Reaction with Co-2(CO)(8) gives the cluster complex 9, in which the (alkynyl)Co-2(CO)(6), group adopts an equatorial position and the hydroxyl and methyl groups are now axial. in contrast, (C5H5)(2)Mo-2(CO)(4) reacts with 6' to produce (2-methyl-1-(phenylethynyl)cyclopentene)Mo-2(CO)(4)-(C5H5)(2), (19). The alkyne, 6' and also the cobalt and molybdenum complexes, 9 and 19 have all been characterized by X-ray crystallography. The observed preference for the bulky (RC=C)Co-2(CO)(6) substituent to occupy an equatorial site in cycloalkanes may be used to rationalize the stereospecificity of the Friedel-Crafts cyclization of cobalt-stabilized propargyl cations onto suitably activated aromatic rings.
• SYNTHESIS OF HALOENONES AND ARYL OR ALKYL SUBSTITUTED ENONES OR ALKENES
  申请人：NEW YORK UNIVERSITY

  公开号：EP0656878A1

  公开（公告）日：1995-06-14
• EP0656878A4
  申请人：——

  公开号：EP0656878A4

  公开（公告）日：1995-07-05
• US5446203A
  申请人：——

  公开号：US5446203A

  公开（公告）日：1995-08-29