1-丙-2-烯基环戊烯 | 37689-19-3

• 分子结构分类: 有机化合物 - 碳氢化合物 - 不饱和烃
• 中文名称: 1-丙-2-烯基环戊烯
• 英文名称: 1-allyl-1-cyclopentene
• 英文别名: 1-allylcyclopentene；1-(2-propenyl)cyclopentene；1-Allyl-cyclopenten-(1)；1-Allyl-cyclopenten；1-prop-2-enylcyclopentene
• CAS: 37689-19-3
• 化学式: C₈H₁₂
• 分子量: 108.183
• InChiKey: PHBGIFRCMRLXFK-UHFFFAOYSA-N

物化性质

• 保留指数：
  822;812.5;818.2;821.6;851;856;812;818;822;822

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  8
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  1-丙-2-烯基环戊烯 、 isopinocampheyl boron dichloride 在 三甲基硅烷 作用下， 以 乙醚 为溶剂， 生成
  参考文献：
  名称：

  Chiral Synthesis via Organoboranes. 48. Efficient Synthesis of Trans-Fused Bicyclic and Cyclic Ketones and Secondary Alcohols in High Optical Purities via Asymmetric Cyclic Hydroboration with Isopinocampheylchloroborane Etherate

  摘要：

  Highly stereo- and enantioselective annelation has been achieved for the synthesis of trans-fused bicyclic and cyclic ketones via the asymmetric cyclic hydroboration of suitable cyclic dienes, such as 1-allyl-1-cycloalkenes or 1-vinyl-1-cycloalkenes and appropriate acyclic 1,4-dienes, respectively, with enantiomerically pure isopinocampheylchloroborane etherate (IpcBHCl . Et2O). The IpcBHCl . Et2O (an 86-90% equilibrium mixture) was readily synthesized by the reaction of an equivalent amount of hydrochloric acid in ethyl ether (Et2O) with optically pure isopinocampheylborane (IpcBH(2)). The hydroboration of the terminal double bond of a representative diene with IpcBHCl . Et2O readily provided the corresponding isopinocampheylalkylchloroborane (IpcRBCl). Subsequent, hydridation of the IpcRBCl with lithium aluminum hydride (LAH, 0.25 equiv) at -20 or -25 degrees C generated the intermediate isopinocampheylalkylborane (IpcRBH) almost instantly, which then underwent a rapid stereospecific and enantioselective intramolecular cyclic hydroboration to provide the intermediate cyclic trialkylborane. This trialkylborane, on treatment with an aldehyde, liberated the optically pure auxiliary as a-pinene (readily recovered for recycle) to provide the corresponding cyclic borinate ester. This ester reacted smoothly with alpha,alpha-dichloromethyl methyl ether (DCME) in the presence of a hindered base (the DCME reaction) to yield, after oxidation with buffered hydrogen peroxide, the trans-fused bicyclic or cyclic ketone in high enantiomeric excess (ee). In another improved approach, in situ generated IpcBHCl . Et2O, from the reduction of isopinocampheyldichloroborane (IpcBCl(2)) with trimethylsilane (Me3SiH), in the presence of representative dienes in Et2O provided considerably improved optical yields of the bicyclic and cyclic ketones. The trialkylboranes obtained from suitable acyclic dienes can be easily protonolyzed to provide the secondary alcohols in high ee.

  DOI：

  10.1021/jo981040c
• 作为产物：
  描述：

  [2-(benzenesulfonyl)-5-[tert-butyl(dimethyl)silyl]oxy-2-prop-2-enylcyclopentyl]-dimethyl-phenylsilane 在 (n-Bu)4F 作用下， 以 四氢呋喃 为溶剂， 以60%的产率得到1-丙-2-烯基环戊烯
  参考文献：
  名称：

  Conversion of vinyl sulfones to regiospecifically functionalized trisubstituted olefins

  摘要：

  Conjugate-addition of phenyldimethylsilyllilthium (or cuprate) to vinyl sulfones followed by in situ alkylation of the alpha-sulfonyl anion provides alpha-alkylated beta-silyl sulfones. Treatment of these materials with fluoride provides trisubstituted olefins via the Kocienski olefin synthesis.

  DOI：

  10.1016/0040-4039(95)00701-d

文献信息

• Convenient ‘one-flask’ synthesis of olefins. Reaction of α-chloroketones with Grignard reagents and lithium
  作者：José Barluenga、Miguel Yus、Pablo Bernad

  DOI：10.1039/c3978000847a

  日期：——

  Olefins and diolefins with the double bonds in predetermined positions are prepared in a one-step process in moderate to good yields by the reaction of α-chloroketones with Grignard reagents and then with lithium.

  通过α-氯酮与格氏试剂然后与锂反应，以一步到中等的产率制备具有预定位置双键的烯烃和二烯烃。
• Barluenga, Jose; Yus, Miguel; Concellon, Jose M., Journal of Chemical Research, Miniprint, 1980, # 2, p. 677 - 692
  作者：Barluenga, Jose、Yus, Miguel、Concellon, Jose M.、Bernad, Pablo

  DOI：——

  日期：——
• Christol et al., Bulletin de la Societe Chimique de France, 1959, p. 543,553
  作者：Christol et al.

  DOI：——

  日期：——
• BARLUENGA J.; YUS M.; CONCELLON J. M.; BERNARD P., J. CHEM. RES. SYNOP., 1980, NO 2, 41/J. CHEM. RES. MIKROFICHE, 0677-0692
  作者：BARLUENGA J.、 YUS M.、 CONCELLON J. M.、 BERNARD P.

  DOI：——

  日期：——
• BARLUENGA J.; YUS M.; BERNAD P., J. CHEM. SOC. CHEM. COMMUN. 1978, NO 19, 847
  作者：BARLUENGA J.、 YUS M.、 BERNAD P.

  DOI：——

  日期：——

表征谱图