1-<(E)-cinnamyloxy>but-2-yne | 168414-99-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-<(E)-cinnamyloxy>but-2-yne
• 英文别名: [(E)-3-but-2-ynoxyprop-1-enyl]benzene
• CAS: 168414-99-1
• 化学式: C₁₃H₁₄O
• 分子量: 186.254
• InChiKey: FMFSBHWYDJHXSN-JXMROGBWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-<(E)-cinnamyloxy>but-2-yne 在 氯化铂 作用下， 以 苯 为溶剂， 反应 0.08h， 以27%的产率得到6-Methyl-7-phenyl-3-oxabicyclo<4.1.0>hept-4-ene
  参考文献：
  名称：

  A Novel platinum tetrachloride-catalyzed cyclorearrangement of allyl propynyl ethers to 3-oxabicyclo[4.1.0]heptenes.

  摘要：

  Allyl propynyl ethers of general formula RC-CCH2OCH2CH=CHR' (1) undergo cyclorearrangement to 3-oxabicyclo[4.1.0]hept-4-enes (2) in oxygen-free benzene upon brief treatment at room temperature with catalytic amount of PtCl4. The transformation of 1 to 2 is assumed to involve platinum-allene intermediates. The structure of 7-(1-naphthyl)-6-phenyl-3-oxabicyclo[4.1.0]hept-4-ene (2c) has been determined by X-ray diffraction analysis. The-naphthyl and phenyl groups were shown to be oriented cis to each other. In the presence of [(CO2)Rh(mu-Cl)](2) the oxabicycloheptenes 2 undergo cyclopropane-ring cleavage. 6,7-Diphenyl-3-oxabicyclo[4.1.0lhept-4-ene (2b) forms the rhodocyclic complex 3b. In the absence of air, the oxygen-free analog of 1a, PhC=C(CH2)(3)CH=CH2 (4), rearranges to the unstable 7-phenylbicyclo[3.2.0]hept-1(7)-ene (5), which can be trapped by oxygen as stable 2-(2-oxo-2-phenylethyl)cyclopentanone (6).

  DOI：

  10.1021/jo00122a043
• 作为产物：
  描述：

  2-丁炔-1-醇 、 Cinnamyl bromide 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 以86%的产率得到1-<(E)-cinnamyloxy>but-2-yne
  参考文献：
  名称：

  Bicyclization of Enynes Using the Cp₂TiCl₂−Mg−BTC System:  A Practical Method to Bicyclic Cyclopentenones

  摘要：

  Bicyclic titanacycles 2 generated with the Cp2TiCl2-Mg-P(OEt)(3) system can be trapped with bis(trichloromethyl) carbonate (BTC) to give bicyclic cyclopentenones 3 in good yields. The titanacycle 2m was isolated and well-identified. Bicyclization of enynes containing 1,2-disubstituted olefin by this method gave good results with excellent stereoselectivity.

  DOI：

  10.1021/jo9810718

文献信息

• Gold(I)-Catalyzed Intermolecular Addition of Carbon Nucleophiles to 1,5- and 1,6-Enynes
  作者：Catelijne H. M. Amijs、Verónica López-Carrillo、Mihai Raducan、Patricia Pérez-Galán、Catalina Ferrer、Antonio M. Echavarren

  DOI：10.1021/jo8014769

  日期：2008.10.3

  Gold(I)-catalyzed addition of carbon nucleophiles to 1,6-enynes gives two different type of products by reaction at the cyclopropane or at the carbene carbons of the intermediate cyclopropyl gold carbenes. The 5-exo-dig cyclization is followed by most 1,6-enynes, although those bearing internal alkynes and alkenes react by the 6-endo-dig pathway. The cyclopropane versus carbene site-selectivity can

  金（I）催化的碳亲核试剂加成到1,6-炔烃中，可通过在中间体环丙基金卡宾的环丙烷或卡宾碳上反应生成两种不同类型的产物。尽管大多数带有内部炔烃和烯烃的烯烃通过6-endo-dig途径反应，但5-exo-dig环化之后是大多数1,6-enynes。在某些情况下，可以通过金催化剂上的配体控制环丙烷对卡宾的位选择性。除了富电子的芳烃和杂芳烃之外，烯丙基硅烷和1,3-二羰基化合物也可以用作亲核试剂。在1，5-烯炔与碳亲核试剂的反应中，优选5-endo-dig途径。
• Trapping bicyclic titanacyclopentenes with bis(trichloromethyl) carbonate (BTC): a new method to bicyclic cyclopentenones
  作者：Zongbao Zhao、Yu Ding

  DOI：10.1039/a708182k

  日期：——

  Bis(trichloromethyl) carbonate is found to trap bicyclic titanacyclopentenes providing a new method for bicyclization of enynes into bicyclic cyclopentenones.

  发现碳酸二（三氯甲基）酯可捕获双环钛环戊烯，这为将烯炔双环化为双环环戊烯酮提供了一种新方法。
• A Novel platinum tetrachloride-catalyzed cyclorearrangement of allyl propynyl ethers to 3-oxabicyclo[4.1.0]heptenes.
  作者：Jochanan Blum、Hanita Beer-Kraft、Yacoub Badrieh

  DOI：10.1021/jo00122a043

  日期：1995.9

  Allyl propynyl ethers of general formula RC-CCH2OCH2CH=CHR' (1) undergo cyclorearrangement to 3-oxabicyclo[4.1.0]hept-4-enes (2) in oxygen-free benzene upon brief treatment at room temperature with catalytic amount of PtCl4. The transformation of 1 to 2 is assumed to involve platinum-allene intermediates. The structure of 7-(1-naphthyl)-6-phenyl-3-oxabicyclo[4.1.0]hept-4-ene (2c) has been determined by X-ray diffraction analysis. The-naphthyl and phenyl groups were shown to be oriented cis to each other. In the presence of [(CO2)Rh(mu-Cl)](2) the oxabicycloheptenes 2 undergo cyclopropane-ring cleavage. 6,7-Diphenyl-3-oxabicyclo[4.1.0lhept-4-ene (2b) forms the rhodocyclic complex 3b. In the absence of air, the oxygen-free analog of 1a, PhC=C(CH2)(3)CH=CH2 (4), rearranges to the unstable 7-phenylbicyclo[3.2.0]hept-1(7)-ene (5), which can be trapped by oxygen as stable 2-(2-oxo-2-phenylethyl)cyclopentanone (6).
• Bicyclization of Enynes Using the Cp₂TiCl₂−Mg−BTC System:  A Practical Method to Bicyclic Cyclopentenones
  作者：Zongbao Zhao、Yu Ding、Gang Zhao

  DOI：10.1021/jo9810718

  日期：1998.12.1

  Bicyclic titanacycles 2 generated with the Cp2TiCl2-Mg-P(OEt)(3) system can be trapped with bis(trichloromethyl) carbonate (BTC) to give bicyclic cyclopentenones 3 in good yields. The titanacycle 2m was isolated and well-identified. Bicyclization of enynes containing 1,2-disubstituted olefin by this method gave good results with excellent stereoselectivity.