cis-2-Ethynylcyclopentan-1-ol | 22022-30-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: cis-2-Ethynylcyclopentan-1-ol
• 英文别名: cis-2-ethynylcyclopentanol；cis-2-Ethinylcyclopentanol；(1S,2S)-2-ethynylcyclopentan-1-ol
• CAS: 22022-30-6；61967-50-8；61967-60-0；67921-28-2；69685-11-6
• 化学式: C₇H₁₀O
• 分子量: 110.156
• InChiKey: JRZIIUSKYKGRDH-RQJHMYQMSA-N

物化性质

• 沸点：
  161.9±29.0 °C(Predicted)
• 密度：
  1.00±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  8
• 可旋转键数：
  0
• 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

安全信息

• 海关编码：
  2906199090

反应信息

• 作为反应物：
  描述：

  cis-2-Ethynylcyclopentan-1-ol 在 三(三苯基膦)羰基氢化铑 、 三苯基膦 、 tin(ll) chloride 、 palladium dichloride 作用下， 以 1,4-二氧六环 为溶剂， 反应 16.0h， 生成 4-methyl-2-oxabicyclo<3.3.0>oct-4-en-3-one
  参考文献：
  名称：

  Palladium-catalyzed cyclocarbonylation of acetylenic alcohols to methylene lactones. Scope and synthesis of appropriate substrates

  摘要：

  DOI：

  10.1021/ja00415a020
• 作为产物：
  描述：

  (+/-)-trans-2-iodocyclopentanol 在 三乙基硼 作用下， 以 正己烷 、 甲苯 为溶剂， 反应 7.0h， 生成 cis-2-Ethynylcyclopentan-1-ol
  参考文献：
  名称：

  The First Radical Method for the Introduction of an Ethynyl Group Using a Silicon Tether and Its Application to the Synthesis of 2‘-Deoxy-2‘-C-ethynylnucleosides¹

  摘要：

  A novel radical method for the stereoselective introduction of an ethynyl group has been developed. When a solution of ethynyldimethylsilyl (EDMS) or [2-(trimethylsilyl)ethynyl]dimethylsilyl (TEDMS) ethers of trans-2-iodoindanol was treated with Et3B followed by tetrabutylammonium fluoride in toluene, atom transfer 5-exo-cyclization and subsequent elimination occurred to give cis-2-ethynylindanol in high yield. The method was shown to be useful in the introduction of an ethynyl group in various five- and six-membered-ring iodohydrins. Furthermore, 2'-deoxy-2'-C-ethynyl-uridine (6) and -cytidine (7), which were designed as novel antimetabolites, were readily synthesized by using this method as the key step. This would be the first example in which a radical reaction was used for introducing an ethynyl group.

  DOI：

  10.1021/jo0206667

文献信息

• Gold-Catalyzed Rearrangement of Allylic Oxonium Ylides: Efficient Synthesis of Highly Functionalized Dihydrofuran-3-ones
  作者：Junkai Fu、Hai Shang、Zhaofeng Wang、Le Chang、Wenbing Shao、Zhen Yang、Yefeng Tang

  DOI：10.1002/anie.201208305

  日期：2013.4.8

  “Diazo” not needed: The title reaction results in the rearrangement of oxonium ylides, which were prepared from readily available homopropargylic allylic ethers instead of diazo compounds, through two different mechanisms: a concerted 2,3‐sigmatropic rearrangement, or a stepwise 1,4‐allyl migration followed by a Claisen rearrangement (see scheme).

  不需要“重氮”：标题反应可导致氧鎓叶立德发生重排，它是通过两种不同的机理由易于获得的均丙烯丙基烯丙基醚代替重氮化合物制备的，它们通过两种不同的机制：协同的2,3-σ重排，或逐步的1， 4烯丙基迁移，然后进行克莱森重排（请参阅方案）。
• Stereoselective synthesis of (Z )-α-(alkoxycarbonyl)methylene β- and γ-lactones by palladium-catalysed oxidative carbonylation of alkynols
  作者：Bartolo Gabriele、Giuseppe Salerno、Francesca De Pascali、Mirco Costa、Gian Paolo Chiusoli

  DOI：10.1039/a603892a

  日期：——

  (Z)-α-(Alkoxycarbonyl)methylene β- and γ-lactones can be obtained in fair to excellent yields and with high catalytic efficiencies by PdI2/KI-catalysed oxidative dialkoxycarbonylation of propynyl alcohols (α,α-dialkyl substituted, or α-monoalkyl substituted with a sufficiently bulky alkyl group) and but-3-yn-1-ols, respectively. Reactions are carried out in alcoholic media under mild conditions (70–80 °C and 20 atm of a 3∶1 mixture of carbon monoxide and air). Reaction pathways are discussed.

  (Z)-δ-(烷氧基羰基)亚甲基δ-和δ-内酯可分别通过 PdI2/KI 催化的丙炔醇（δ,δ-二烷基取代，或δ-单烷基被足够大的烷基取代）和丁-3-炔-1-醇的氧化二烷氧基羰基化反应，以相当好到极好的产率和较高的催化效率获得。反应在酒精介质中温和进行（70â80 °C，20 atm 的一氧化碳和空气 3â¶1 混合物）。对反应途径进行了讨论。
• Selective reductive cleavage of the propargyl oxygen bond of acetylenic epoxides. A general synthesis of 2-ethynylcycloalkanones
  作者：Robert G. Carlson、William W. Cox

  DOI：10.1021/jo00434a009

  日期：1977.7
• Substituent effects on the SmI2/Pd(0)-promoted carbohydrate ring-contraction of 5-alkynylpyranosides
  作者：José M. Aurrecoechea、Jesús H. Gil、Beatriz López

  DOI：10.1016/s0040-4020(03)01103-7

  日期：2003.9

  The effect of substituents on the reactivity and stereoselectivity of the SmI2/Pd(0)-promoted ring-contraction of 5-alkynylpyranosides has been examined using substrates substituted only at selected positions. While formation of 2-ethynylcyclopentanols takes place efficiently, an internal alkyne did not afford the expected product. The presence of peripheral alkoxy substituents leads to variable stereoselectivities that depend on the number and orientation of such groups. Thus, an isolated OBn substituent at C(3) (carbohydrate numbering) exerts a significant stereochemical control while additional substitution with the same group at C(4) either enhances or drastically reduces stereoselectivity depending on its orientation (alpha or beta, respectively). (C) 2003 Elsevier Ltd. All rights reserved.
• HANACK, M.;AUCHTER, G., J. AMER. CHEM. SOC., 1985, 107, N 18, 5238-5245
  作者：HANACK, M.、AUCHTER, G.

  DOI：——

  日期：——