cis-2-vinylcyclopentanol | 136357-54-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: cis-2-vinylcyclopentanol
• 英文别名: cis-2-Vinyl-1-cyclopentanol；(1S,2S)-2-ethenylcyclopentan-1-ol
• CAS: 136357-54-5
• 化学式: C₇H₁₂O
• 分子量: 112.172
• InChiKey: VROPFTPHFBHMLL-RQJHMYQMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  8
• 可旋转键数：
  1
• 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：

  苯甲酰氯 、 cis-2-vinylcyclopentanol 在 吡啶 作用下， 反应 2.0h， 以62 mg的产率得到(+/-)-cis-1-benzoyloxy-2-vinylcyclopentane
  参考文献：
  名称：

  A One-Pot Method for the Stereoselective Introduction of a Vinyl Group via an Atom-Transfer Radical-Cyclization Reaction with a Diphenylvinylsilyl Group as a Temporary Connecting Tether. Synthesis of 4‘α-C-Vinylthymidine, a Potent Antiviral Nucleoside¹

  摘要：

  A one-pot method for the stereoselective introduction of a vinyl group at the beta-position of a hydroxyl group in halohydrins or alpha-phenylselenoalkanols via an atom-transfer radical-cyclization reaction was developed. When a solution of the diphenylvinylsilyl ether of (+/-)-trans-2-iodoindanol (2a) and (Bu3Sn)(2) in benzene was irradiated with a high-pressure mercury lamp, the corresponding atom transfer 5-exo-cyclization product was produced, which in turn was treated with tetrabutylammonium fluoride to give cis-2-vinylindanol (3) in 82% yield from 2a. Similar reactions with diphenylvinylsilyl ethers of (+/-)trans-1-phenylselenoindan-2-ol (4), trans-2-iodocyclopentanol (6), and trans-2-iodocyclohexanol (8) gave the corresponding vinyl derivatives. Furthermore, this reaction was successfully applied to the synthesis of 4'alpha-C-vinylthymidine, a potent antiviral nucleoside.

  DOI：

  10.1021/jo990787f
• 作为产物：
  描述：

  7-bromo-hept-5t-enal 生成 cis-2-vinylcyclopentanol
  参考文献：
  名称：

  立体反应由醛类和格利雅德类与烯丙基酮反应

  摘要：

  醛R-CHO（R = Me，Et，iPr，tBu）与烯丙基（巴豆基和β，γ-二甲基烯丙基溴化镁）和仲烷基[仲丁基溴化镁和（1,2-二甲基丙基）氯化镁]反应试剂以形成非对映异构的醇对R'-CHMeCHOH-R（R'= CH 2 = CH 3，CH 2 = CMe E，Et和iPr）。涉及二级烷基格氏试剂的反应不是立体选择性的；反之亦然。那些涉及烯丙基格利雅试剂的试剂显示出一定的立体选择性，其方向和大小取决于试剂和醛的结构。

  DOI：

  10.1016/s0040-4020(01)92953-9

文献信息

• Tin-promoted stereocontrolled intramolecular allylation of carbonyl compounds: a facile and stereoselective method for ring construction
  作者：Jing-Yao Zhou、Zhao-Gen Chen、Shi-Hui Wu

  DOI：10.1039/c39940002783

  日期：——

  The intramolecular allylation of carbonyl compounds 1 promoted by metallic tin proceeds in a stereocontrolled manner to give cyclic products 2 with high diastereoselectivity.

  金属锡催化的羰基化合物1的分子内烯丙基化反应以立体控制的方式进行，生成具有高Diastereoselectivity的环状产物2。
• Radical Group Transfer of Vinyl and Alkynyl Silanes Driven by Photoredox Catalysis
  作者：Floriane Baussière、Marius M. Haugland

  DOI：10.1021/acs.joc.3c01213

  日期：2023.9.1

  protocol for the radical group transfer of vinyl and alkynyl silanes onto sp3 carbons, using activated and unactivated iodides as radical precursors. Our method displays high diastereoselectivity and excellent functional group tolerance, and enables direct formation of group transfer products by in situ ring opening. Mechanistic investigations revealed that the reaction proceeds via an unusual dual

  自由基基团转移是形成 C-C 键的有力工具。这些过程通常涉及 C-C π 键的自由基加成，然后是所得环状中间体的断裂。尽管有机硅烷在这方面具有有利的不稳定性，但硅束缚的自由基受体基团在自由基基团转移反应中仍未得到充分研究。我们报告了一种通用的光氧化还原催化方案，使用活化和未活化的碘化物作为自由基前体，将乙烯基和炔基硅烷的自由基基团转移到 sp 3碳上。我们的方法表现出高非对映选择性和优异的官能团耐受性，并且能够通过原位开环直接形成基团转移产物。机理研究表明，该反应通过不寻常的双催化循环进行，导致整体氧化还原中性过程。
• SYNTHESIS OF DIASTEREOMERICALLY ENRICHED CYCLIC HOMOALLYLIC ALCOHOLS USING MOLYBDENUM π-ALLYL COMPLEXES
  作者：Marie E. Krafft、Peter Schmidt

  DOI：10.1081/scc-120006039

  日期：2002.1

  Condensation of CpMo(NO)(pi-allyl)I complexes bearing a tethered aldehyde gave cyclic homoallylic alcohols with a varying degree of diastereoselectivity. Cyclohexyl and tetrahydronaphthyl derivatives were prepared in moderate to good yields. The diastereoselectivity is highly dependent on the substituents on the ring.
• Zirconium-mediated, highly diastereoselective ring contraction of carbohydrate derivatives: synthesis of highly functionalized, enantiomerically pure carbocycles
  作者：Hisanaka Ito、Yoshiteru Motoki、Takeo Taguchi、Yuji Hanzawa

  DOI：10.1021/ja00072a045

  日期：1993.9
• Hoffmann, Reinhard W.; Niel, Gilles, Liebigs Annalen der Chemie, 1991, # 11, p. 1195 - 1201
  作者：Hoffmann, Reinhard W.、Niel, Gilles

  DOI：——

  日期：——