3-methyl-3-vinylcyclohexan-1-one | 68269-56-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-methyl-3-vinylcyclohexan-1-one
• 英文别名: 3-ethenyl-3-methylcyclohexanone；3-methyl-3-vinylcyclohexanone；3-Methyl-3-vinyl-cyclohexan-1-on；3-Methyl-3-vinylcyclohexanon；3-ethenyl-3-methylcyclohexan-1-one
• CAS: 68269-56-7；54735-44-3
• 化学式: C₉H₁₄O
• 分子量: 138.21
• InChiKey: MIRPXLBBGORDCA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 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-methyl-3-vinylcyclohexan-1-one 在 对甲苯磺酸 作用下， 生成 3-methylcyclohexanone-3-acetic acid
  参考文献：
  名称：

  Conformational consequences of intramolecular cyclopropanation within small bicyclic systems.

  摘要：

  DOI：

  10.1016/s0040-4039(00)80071-4
• 作为产物：
  描述：

  在 氢氟酸 作用下， 以 甲醇 为溶剂， 生成 3-methyl-3-vinylcyclohexan-1-one
  参考文献：
  名称：

  Total Synthesis of Hapalindoles J and U

  摘要：

  The total synthesis of D,L-hapalindoles J and U has been accomplished. Hapalindole J was prepared in 11% overall yield over 11 synthetic steps and hapalindole U was prepared in 25% overall yield over 13 synthetic steps from commercially available materials. The route employs a novel silyl ether-based strategy for accessing the 6:5:6:6 ring system of the hapafindoles rapidly and in good yields.

  DOI：

  10.1021/jo202139k

文献信息

• Formation of Quaternary Stereogenic Centers by Copper-Catalyzed Asymmetric Conjugate Addition Reactions of Alkenylaluminums to Trisubstituted Enones
  作者：Daniel Müller、Alexandre Alexakis

  DOI：10.1002/chem.201302856

  日期：2013.11.4

  undergo asymmetric copper‐catalyzed conjugate addition (ACA) to β‐substituted enones allowing the formation of stereogenic all‐carbon quaternary centers. Phosphinamine–copper complexes proved to be particularly active and selective compared with phosphoramidite ligands. After extensive optimization, high enantioselectivities (up to 96 % ee) were obtained for the addition of alkenylalanes to β‐substituted

  烯基铝经过不对称的铜催化共轭加成（ACA）至β取代的烯酮，从而形成立体立体的全碳四元中心。与亚磷酰胺配体相比，膦胺-铜络合物被证明具有特别的活性和选择性。经过广泛的优化后，将烯基丙氨酸添加到β-取代的烯酮中获得了很高的对映选择性（高达ee的96％  ）。为了产生芳基和烷基取代的烯基亲核试剂，探索了两种生成必需的烯基铝的策略。此外，首次将烷基取代的次膦胺（SimplePhos）配体鉴定为Cu催化的ACA的高效配体。
• Synthetic studies of marine alkaloids hapalindoles. Part I Total synthesis of (±)-hapalindoles J and M
  作者：Hideaki Muratake、Mitsutaka Natsume

  DOI：10.1016/s0040-4020(01)96005-3

  日期：——

  The first concise synthesis of marine indole alkaloids (±)-hapalindoles J (4) and M (5) was achieved in seven or six steps starting from a readily available compound 6 using important key reactions, 6 → 7 → and 8 and 35 → 41 or 5.

  海洋吲哚生物碱（±）-单吲哚J（4）和M（5）的第一个简明合成是通过使用重要的关键反应6→7→以及8和35→从现成的化合物6开始以七六步完成的41或5。
• Iridium-Catalyzed Alkene-Selective Transfer Hydrogenation with 1,4-Dioxane as Hydrogen Donor
  作者：Deliang Zhang、Tomohiro Iwai、Masaya Sawamura

  DOI：10.1021/acs.orglett.9b01989

  日期：2019.8.2

  using 1,4-dioxane as a hydrogen donor is described. The use of 1,2-bis(dicyclohexylphosphino)ethane (DCyPE), featuring bulky and highly electron-donating properties, led to high catalytic activity. A polystyrene-cross-linking bisphosphine PS-DPPBz produced a reusable heterogeneous catalyst. These homogeneous and heterogeneous protocols achieved chemoselective transfer hydrogenation of alkenes over

  描述了使用1，4-二恶烷作为氢供体的铱催化的烯烃的转移加氢。1,2-双（二环己基膦基）乙烷（DCyPE）的使用具有体积大和给电子高的特性，因此具有很高的催化活性。聚苯乙烯交联双膦PS-DPPBz产生了可重复使用的非均相催化剂。这些均质和非均质的方案实现了烯烃在其他可能还原的官能团（例如同一分子中的羰基，硝基，氰基和亚氨基）上的化学选择性转移加氢。
• Asymmetric Synthesis of 6′-Hydroxyarenarol: The Proposed Biosynthetic Precursor to Popolohuanone E
  作者：Rachel H. Munday、Ross M. Denton、James C. Anderson

  DOI：10.1021/jo801404u

  日期：2008.10.17

  The first synthesis of (+)-6'-hydroxyarenarol 3, the proposed biogenetic precursor to popolohuanone E (1), is described. An enantioselective route to key iodide intermediate 12 has been developed allowing the asymmetric synthesis of the known cis-decalin 22. Conditions which allow the removal of the methyl ether protecting groups on the hydroxyarene leaving the exocyclic methylene moiety in tact have

  描述了（+）-6'-羟基芳烃3的首次合成，这是拟定的Popolohuanone E（1）的生物遗传前体。已经开发了对关键碘化物中间体12的对映选择性路线，从而允许不对称合成已知的顺式十氢萘22。已经开发了条件，该条件允许去除羟基芳烃上的甲基醚保护基，而使环外亚甲基部分保持完整。这个综合。
• Effects of gengenions on organocuprate reactivity/selectivity: Higher order, mixed lithio- cyanocuprates
  作者：Bruce H. Lipshutz、Edmund L. Ellsworth、James R. Behling、Arthur L. Campbell

  DOI：10.1016/s0040-4039(00)82475-2

  日期：1988.1

  Several different types of reactions characteristic of organocuprates have been studied using reagents RTRRCu(CN)LiNa derived from CuCN and one equivalent each of an organolithium (RTLi) and organosodium (RRNa) species.

  已经使用衍生自CuCN的试剂R T R R Cu（CN）LiNa以及有机锂（R T Li）和有机钠（R R Na）物种中的每一个当量来研究几种不同类型的有机铜酸盐特征反应。