1-chlorohex-2-en-4-yne | 53247-02-2

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 有机氯化物
• 英文名称: 1-chlorohex-2-en-4-yne
• 英文别名: 1-Chlor-hex-2-en-4-in；1-Chlorohex-2-EN-4-yne
• CAS: 53247-02-2
• 化学式: C₆H₇Cl
• mdl: MFCD19237098
• 分子量: 114.575
• InChiKey: GWQWEVZXSMSWHH-UHFFFAOYSA-N

物化性质

• 沸点：
  167.4±23.0 °C(Predicted)
• 密度：
  0.988±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  7
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.333
• 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：

  2-环己烯-1-酮 、 1-chlorohex-2-en-4-yne 生成 1-hex-2-en-4-ynylcyclohex-2-en-1-ol
  参考文献：
  名称：

  乙烯基亚烷基-V（xf†）：镁的乙烯基反应，丙酮和丙酮的共轭反应和易位反应，最终得到醇

  摘要：

  由5-卤代烷-3-烯-1-炔制备的乙烯基烯格利雅试剂与无环共轭醛和酮反应，仅生成4-乙炔基六1,5-二烯3-醇5；在环己烯酮和其他酮的共轭作用更广泛的情况下，相同的醇5仍是主要产物，但由于试剂的另外两个亲核位点的介入，也获得了异构体酮和醇。醇5通过在二甘醇二甲醚中的溶液回流或通过在加热至350°的柱上快速蒸馏而容易地异构化为δ-烯属ξ-炔醛和酮6。

  DOI：

  10.1016/0040-4020(77)84075-1

文献信息

• A novel tungsten-mediated carbonylation reaction via a tandem 1,3-metal sigmatropic shift through a σ-hex-2-en-4-yn-1-yl group
  作者：Liang Kwei-Wen、Gene-Hsian Lee、Shie-Ming Peng、Rai-Shung Liu

  DOI：10.1039/c39940002705

  日期：——

  [W(η-C5H5)(CO)3(σ-trans-CH2CHCHCCMe)] with RXH (RXH = H2O, MeOH, NH2Bui) over silica or Florisil gel leads to a new carbonylation reaction to give [W(η-C5H5)(CO)2(η3-3-syn-RXCO-3-anti-Me-1-vinylallyl)] compounds in moderate yields, providing direct evidence for a tandem 1,3-metal shift across conjugated allyl and alkyne bonds.

  [W（η-C的THF溶液搅拌5 ħ 5）（CO）3（σ-反式-CH 2 CH CHC CME）]与RXH（RXH = H 2 O，甲醇，NH 2卜我）在硅胶上或硅酸镁凝胶通向新的羰基化反应，得到[W（η-C 5 H ^ 5）（CO）2（η 3 -3-顺-RXCO -3-抗在中等产率-Me -1- vinylallyl）]化合物，提供了共轭的烯丙基和炔键串联1,3-金属转移的直接证据。
• Dulcere,J.P. et al., Bulletin de la Societe Chimique de France, 1974, p. 1119 - 1123
  作者：Dulcere,J.P. et al.

  DOI：——

  日期：——
• Alkylation d'enamines par les halogeno-5 ene-3 ynes-1
  作者：A. Douthea、J. Gore

  DOI：10.1016/0040-4020(76)80110-x

  日期：1976.1
• Alkoxycarbonylation Reaction Involving a Tandem 1,3-Metal Shift across Conjugated Allyl and Alkyne Bonds
  作者：Kwei-Wen Liang、Gene-Hsiang Lee、Shie-Ming Peng、Rai-Shung Liu

  DOI：10.1021/om00005a036

  日期：1995.5

  The reaction between CpW(CO)(3)Na and 1-chlorohex-2-en-4-yne (1; cis/trans = 1/4) gave CpW(CO)(3)(eta(1)-hex-2-en-4-yn-1-yl) (2) in good yield (cis/trans = 1/4). The cis/trans isomers of 2 were separated on a silica column at 0 degrees C. Treatment of the trans isomer 2a with TCNE gave the [3 + 2] cycloaddition product exclusively to retain the eta(1)-allyl activity. Addition of CF3SO3H (1.1 equiv) to 2a in cold diethyl ether in the presence of CH3OH gave CpW(CO)(3)(eta(1)-trans-4-oxo-2-hexen-1-yl) (5) in 61% yield. Stirring of 2a with RXH (RXH = H2O, MeOH, Me(2)CHCH(2)NH(2)) in THF over Florisil at 30 degrees C led to a new carbonylation to give CpW(CO)(2)(eta(3)-1-syn-COXR-1-anti-Me-3-syn-vinylallyl) compounds (RX = OH (6), MeO (7), Me(2)CHCH(2)NH (8)) in 52-18% yields. The reaction of CpW(CO)(3)Na and 1-chloro-8-hydroxy-2-octen-4-yne gave the corresponding eta(1)-anyl compound which on a silica column produced the intramolecular alkoxycarbonylation product 13 in moderate yield. In the presence of BF3 . Et(2)O, compound 7 reacted with aldehydes and unsaturated enones to give eta(4)-diene salts, which after demetalation by Me(3)NO liberated organic products in 40-55% isolated yields.
• Vinylallenes—V(xf†)
  作者：M.L. Roumestant、P. Place、J. Gore

  DOI：10.1016/0040-4020(77)84075-1

  日期：1977.1

  Vinylallenic Grignard reagents prepared from 5-halogeno alk-3-ene-1-ynes react with acyclic conjugated aldehydes and ketones leading exclusively to 4-ethynyl hexa 1,5-diene 3-ols 5; with cyclohexénone and other ketones having more extended conjugation, the same alcohol 5 is still the major product but isomeric ketones and alcohols are also obtained resulting from the intervention of the two other nucleophilic

  由5-卤代烷-3-烯-1-炔制备的乙烯基烯格利雅试剂与无环共轭醛和酮反应，仅生成4-乙炔基六1,5-二烯3-醇5；在环己烯酮和其他酮的共轭作用更广泛的情况下，相同的醇5仍是主要产物，但由于试剂的另外两个亲核位点的介入，也获得了异构体酮和醇。醇5通过在二甘醇二甲醚中的溶液回流或通过在加热至350°的柱上快速蒸馏而容易地异构化为δ-烯属ξ-炔醛和酮6。