3-(but-3-en-1-yl)-3-methylcyclohexan-1-one | 121363-31-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-(but-3-en-1-yl)-3-methylcyclohexan-1-one
• 英文别名: 3-But-3-enyl-3-methylcyclohexan-1-one
• CAS: 121363-31-3
• 化学式: C₁₁H₁₈O
• 分子量: 166.263
• InChiKey: LCGSPZATXCEWHJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-(but-3-en-1-yl)-3-methylcyclohexan-1-one 在 四氢吡咯 、 二甲基硫 、 potassium tert-butylate 、 臭氧 、 溶剂黄146 作用下， 以 四氢呋喃 、 苯 为溶剂， 反应 24.0h， 生成 Ethyl (1R*,3aS*,7aR*)-α--hexahydro-3a-methyl-7-methylene-1-indanacetate
  参考文献：
  名称：

  Synthetic approaches to the axane family of sesquiterpenoids. Total synthesis of (dl)-axamide-4, (dl)-axisonitrile-4, and (dl)-axisothiocyanate-4

  摘要：

  Two methods for the preparation of perhydroindan 7 are described. One involves an intramolecular free radical cyclization in a key step and proceeds in 13 steps and 9% yield from anisole (9). The other involves an intramolecular conjugate addition mediated by pyrrolidine (28 --> 7) and proceeds in five steps and 30% overall yield from vinylogous ester 29. Two unsuccessful attempts to convert 7 into axane sesquiterpenoids 1-6 are described. The synthesis of axanes 4-6 was achieved using a potassium tert-butoxide catalyzed cyclization of a dienoic keto ester as a key step (47 + 48 --> 49). Conversion of alpha,beta-unsaturated ester 49 to vinyl isocyanate 57 was accomplished using a Curtius rearrangement and reduction of 57 with lithium triethylborohydride completed the synthesis of axamide-4 (4). The preparation of axisonitrile-4 (5) and axisothiocyanate-4 (6) from 4 is also described.

  DOI：

  10.1021/jo00033a023
• 作为产物：
  描述：

  3-(but-3-enyl)-3-methyl-1-trimethylsilyloxycyclohexene 在 盐酸 、 碳酸氢钠 、 间氯过氧苯甲酸 作用下， 以 乙醚 、 乙醇 为溶剂， 反应 5.67h， 生成 3-(but-3-en-1-yl)-3-methylcyclohexan-1-one
  参考文献：
  名称：

  Brown, David S.; Marples, Brian A.; Spilling, Christopher D., Journal of the Chemical Society. Perkin transactions I, 1988, p. 2033 - 2036

  摘要：

  DOI：

文献信息

• Simple Construction of Bicyclo[4.3.0]nonane, Bicyclo[3.3.0]octane, and Related Benzo Derivatives by Palladium-Catalyzed Cycloalkenylation
  作者：Masahiro Toyota、Andivelu Ilangovan、Rei Okamoto、Tomohito Masaki、Makoto Arakawa、Masataka Ihara

  DOI：10.1021/ol020187u

  日期：2002.11.1

  [reaction: see text] Bicyclo[4.3.0]nonanes (hydrindanes) and bicyclo[3.3.0]octanes (octahydropentalenes) are easily synthesized by palladium-catalyzed cycloalkenylations. Additionally, benzo-fused bicyclo[3.3.0]octanes are prepared for the first time through intramolecular coupling between silyl enol ethers and aromatic rings in the presence of catalytic palladium acetate.

  [反应：见正文]双环[4.3.0]壬烷（氢化丙烷）和双环[3.3.0]辛烷（八氢戊烯）很容易通过钯催化的环烯基化反应合成。另外，在乙酸钯催化作用下，通过甲硅烷基烯醇醚与芳环之间的分子内偶联，首次制备了苯并稠合的双环[3.3.0]辛烷。
• Access to Functionalized Quaternary Stereocenters via the Copper-Catalyzed Conjugate Addition of Monoorganozinc Bromide Reagents Enabled by <i>N</i>,<i>N-</i>Dimethylacetamide
  作者：Tyler J. Fulton、Phebe L. Alley、Heather R. Rensch、Adriana M. Ackerman、Cameron B. Berlin、Michael R. Krout

  DOI：10.1021/acs.joc.8b02201

  日期：2018.12.7

  reagents, readily obtained from alkyl bromides, display excellent reactivity with β,β-disubstituted enones and TMSCl in the presence of Cu(I) and Cu(II) salts to synthesize a variety of cyclic functionalized β-quaternary ketones in 38–99% yields and 9:1–20:1 diastereoselectivities. The conjugate addition features a pronounced improvement in DMA using monoorganozinc bromide reagents. A simple one-pot protocol

  易于从烷基溴化物中获得的单有机锌试剂，在存在铜（Ⅰ）和铜（Ⅱ）盐的情况下，与β，β-二取代的烯酮和TMScl具有优异的反应活性，可以在38-99的范围内合成各种环状官能化的β-季酮。 ％的收率和9：1–20：1的非对映选择性。使用溴化单有机锌试剂可显着改善共轭物的DMA。利用原位生成的单有机锌试剂的简单一锅操作方案可提供相当的产品产量。
• Zinc-mediated anionic cyclization of unstabilized ketone enolates with unactivated alkenes
  作者：Diego Olivieri、David Huang、Alexandra K. Bodnar、Shijin Yu、Timothy R. Newhouse

  DOI：10.1016/j.tet.2020.131417

  日期：2020.12

  We report herein general conditions for a zinc-mediated anionic cyclization of unstabilized ketone enolates. This anionic cyclization allows access to various carbocyclic architectures by utilizing abundant ketones and unactivated alkenes as precursors. The transformation is enabled by the use of Zn(TMP)2 as base and Zn(OTf)2 as an additive. The resulting alkylzinc species can be intercepted by electrophiles

  我们在此报告了不稳定的酮烯酸酯的锌介导的阴离子环化的一般条件。通过利用丰富的酮和未活化的烯烃作为前体，这种阴离子环化反应可以进入各种碳环结构。通过使用Zn（TMP）2作为碱和Zn（OTf）2作为添加剂可以实现转化。最终的烷基锌物质可被亲电体拦截，形成串联的C–X和C–O键。
• Total Synthesis of Allocyathin B₂, a Metabolite of Bird's Nest Fungi
  作者：Motoo Tori、Naoko Toyoda、Masakazu Sono

  DOI：10.1021/jo971514s

  日期：1998.1.1

  Allocyathin B-2 has been synthesized using aldol reactions for construction of rings A and B, introduction of the side chain for ring B, cyclization of the acetyl group into a lactone, and construction of the seven-membered diene aldehyde during the last step.
• HART, DAVID J.;LAI, CHIN-SHAN, SYNLETT.,(1989) N, C. 49-51
  作者：HART, DAVID J.、LAI, CHIN-SHAN

  DOI：——

  日期：——