1-(1-cyclopropylethenyl)naphthalene | 418763-99-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-(1-cyclopropylethenyl)naphthalene
• 英文别名: 1-(1-cyclopropylvinyl)naphthalene
• CAS: 418763-99-2
• 化学式: C₁₅H₁₄
• mdl: MFCD09030300
• 分子量: 194.276
• InChiKey: OJOCZDBVPZTUCO-UHFFFAOYSA-N

物化性质

• 沸点：
  325.4±9.0 °C(Predicted)
• 密度：
  1.087±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  diiron nonacarbonyl 、 1-(1-cyclopropylethenyl)naphthalene 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 叔丁醇 、 二氯甲烷 为溶剂， 反应 12.5h， 以68%的产率得到3-(1-naphthyl)cyclohex-2-enone
  参考文献：
  名称：

  Fe 2（CO）9介导的乙烯基环丙烷与CO的[5 + 1]环加成反应，合成α，β-环己烯酮

  摘要：

  已经开发出Fe 2（CO）9介导的乙烯基环丙烷（VCP）和CO与α，β-环己烯酮的[5 + 1]环加成反应。该反应可以耐受VCPsα位的芳基和脂族基团，而带有乙烯基或炔基取代基的VCP底物不是合适的。另外，如果芳基连接至底物的乙烯基部分，则该反应也可用于合成双环。与Fe（CO）5介导的[5 + 1]反应相比，便宜，安全的Fe 2（CO）9的使用和放弃光辐照条件是本方法的两个主要优点。

  DOI：

  10.1016/j.tet.2016.01.046
• 作为产物：
  描述：

  1-Cyclopropylethynyl-2-(1-methoxy-but-3-enyl)-benzene 在 platinum(II) bromde 作用下， 以 1,4-二氧六环 为溶剂， 反应 93.0h， 以50%的产率得到1-(1-cyclopropylethenyl)naphthalene
  参考文献：
  名称：

  PtBr₂-Catalyzed Consecutive Enyne Metathesis−Aromatization of 1-(1-Methoxy-but-3-enyl)-2-(1-alkynyl)benzenes:  Dual Role of the Pt Catalyst

  摘要：

  1,7-Enynes 1, connected through an aromatic ring and bearing a leaving methoxy group at the 4-position, underwent the PtBr2-catalyzed enyne metathesis followed by aromatization in one pot to afford vinyl naphthalenes 3 in good to acceptable yields. The cyclobutene intermediate 11a and another intermediate 2a were isolated, indicating that PtBr2 acts as a dual role catalyst: (1) as a transition metal catalyst, it induces the eryne metathesis to produce 11a starting from 1a, and (2) as a Lewis acid catalyst, it facilitates elimination of MeOH from 2a to give the aromatized product 3a.

  DOI：

  10.1021/jo048273q

文献信息

• B(C₆F₅)₃-Catalyzed Hydrosilylation of Vinylcyclopropanes
  作者：Peng-Wei Long、Tao He、Martin Oestreich

  DOI：10.1021/acs.orglett.0c02751

  日期：2020.9.18

  reported. For the majority of VCPs, little or no ring opening of the cyclopropyl unit is observed. Conversely, for VCPs with bulky R groups, such as ortho-substituted aryl rings or branched alkyl residues, ring opening is the exclusive reaction pathway. This finding is explained by the thwarted hydride delivery to a sterically shielded, β-silicon-stabilized cyclopropylcarbinyl cation intermediate.

  据报道，强硼路易斯酸B（C 6 F 5）3催化乙烯基环丙烷（VCP）的硅氢化。对于大多数VCP，观察到很少或没有环丙基单元的开环。相反，对于具有庞大R基团的VCP，例如邻位取代的芳基环或支链烷基残基，开环是唯一的反应途径。这一发现可以通过阻止氢化物向空间屏蔽的，β-硅稳定的环丙基羰基阳离子中间物的传递来解释。
• Radical 1,5-Chloropentafluorosulfanylation of Unactivated Vinylcyclopropanes and Transformation into α-SF₅ Ketones
  作者：Fang-Fang Feng、Jun-An Ma、Dominique Cahard

  DOI：10.1021/acs.joc.1c01886

  日期：2021.10.1

  5-chloropentafluorosulfanylation of vinyl cyclopropanes (VCPs) initiated by Et3B/O2 affords allylic pentafluorosulfanyl/homoallylic chloride products through the ring-strain release of the cyclopropane. The VCP substitution pattern was investigated. The utility of this reaction was illustrated in post-transformation of the C═C bond by ozonolysis, giving access to valuable α-SF5 carbonyl compounds.

  由 Et 3 B/O 2引发的乙烯基环丙烷 (VCP) 的自由基 1,5-氯五氟硫烷基化通过环丙烷的环应变释放提供烯丙基五氟硫烷基/高烯丙基氯产物。研究了 VCP 取代模式。该反应的效用在通过臭氧分解 C=C 键的后转化中得到了说明，从而获得了有价值的 α-SF 5羰基化合物。
• PtBr₂-Catalyzed Consecutive Enyne Metathesis−Aromatization of 1-(1-Methoxy-but-3-enyl)-2-(1-alkynyl)benzenes:  Dual Role of the Pt Catalyst
  作者：Gan B. Bajracharya、Itaru Nakamura、Yoshinori Yamamoto

  DOI：10.1021/jo048273q

  日期：2005.2.1

  1,7-Enynes 1, connected through an aromatic ring and bearing a leaving methoxy group at the 4-position, underwent the PtBr2-catalyzed enyne metathesis followed by aromatization in one pot to afford vinyl naphthalenes 3 in good to acceptable yields. The cyclobutene intermediate 11a and another intermediate 2a were isolated, indicating that PtBr2 acts as a dual role catalyst: (1) as a transition metal catalyst, it induces the eryne metathesis to produce 11a starting from 1a, and (2) as a Lewis acid catalyst, it facilitates elimination of MeOH from 2a to give the aromatized product 3a.
• Fe2(CO)9-mediated [5+1] cycloaddition of vinylcyclopropanes and CO for the synthesis of α, β-cyclohexenones
  作者：Cheng-Hang Liu、Zhe Zhuang、Sritama Bose、Zhi-Xiang Yu

  DOI：10.1016/j.tet.2016.01.046

  日期：2016.6

  A Fe2(CO)9-mediated [5+1] cycloaddition of vinylcyclopropanes (VCPs) and CO to α, β-cyclohexenones has been developed. The reaction can tolerate aryl and aliphatic groups at the α-position of VCPs, while VCP substrates with vinyl or alkynyl substitutions are not suitable ones. In addition, this reaction can also be used to synthesize bicyclic rings if an aryl group is attached to the vinyl moiety of

  已经开发出Fe 2（CO）9介导的乙烯基环丙烷（VCP）和CO与α，β-环己烯酮的[5 + 1]环加成反应。该反应可以耐受VCPsα位的芳基和脂族基团，而带有乙烯基或炔基取代基的VCP底物不是合适的。另外，如果芳基连接至底物的乙烯基部分，则该反应也可用于合成双环。与Fe（CO）5介导的[5 + 1]反应相比，便宜，安全的Fe 2（CO）9的使用和放弃光辐照条件是本方法的两个主要优点。