2-(cyclopent-1-enyl)ethylbenzene | 4413-18-7

• 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: 2-(cyclopent-1-enyl)ethylbenzene
• 英文别名: 1-phenethylcyclopentene；1-cyclopent-1-enyl-2-phenyl-ethane；1-Cyclopent-1-enyl-2-phenyl-aethan；[2-(1-Cyclopenten-1-yl)ethyl]benzene；2-(cyclopenten-1-yl)ethylbenzene
• CAS: 4413-18-7
• 化学式: C₁₃H₁₆
• 分子量: 172.27
• InChiKey: RFNBXIZHABVLTK-UHFFFAOYSA-N

物化性质

• 沸点：
  265.1±10.0 °C(Predicted)
• 密度：
  0.966±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  1-溴-3-苯基丙烷 在 六甲基磷酰三胺 、 正丁基锂 、 4 A molecular sieve 、 potassium tert-butylate 、 四丁基氟化铵 、 sodium hydride 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 26.58h， 生成 2-(cyclopent-1-enyl)ethylbenzene
  参考文献：
  名称：

  Scarpetti, David; Fuchs, Philip L., Journal of the American Chemical Society, 1990, vol. 112, # 22, p. 8084 - 8090

  摘要：

  DOI：

文献信息

• ω-Ethylenic Allylic Substrates as Alternatives to Cyclic Substrates in Copper- and Iridium-Catalyzed Asymmetric Allylic Alkylation
  作者：Francesca Giacomina、David Riat、Alexandre Alexakis

  DOI：10.1021/ol100162y

  日期：2010.3.19

  A new strategy to access highly enantioenriched cyclic compounds (up to 98%) is proposed using ω-ethylenic allylic substrates through a one-pot asymmetric allylic alkylation and ring-closing metathesis. Such starting compounds can be seen as synthetic equivalents of cyclic allylic substrates.

  提出了一种新的策略来获得高度对映体富集的环状化合物（高达98％），该方法使用ω-乙烯烯丙基烯丙基底物通过一锅不对称烯丙基烯丙基烷基化和闭环复分解反应。此类起始化合物可视为环状烯丙基底物的合成等同物。
• Denissenko, Chemische Berichte, 1936, vol. 69, p. 2183,2185
  作者：Denissenko

  DOI：——

  日期：——
• Regio- and Enantioselective Substitution of Primary Endocyclic Allylic Sulfoximines with Organocopper and Organocuprate Reagents. The Importance of Iodide for the Allylic Substitution with Organocopper Compounds
  作者：Hans-Joachim Gais、Harald Mueller、Joerg Bund、Matthias Scommoda、Jochen Brandt、Gerhard Raabe

  DOI：10.1021/ja00114a009

  日期：1995.3

  The endocyclic N-substituted allylic sulfoximines 17-20 and 26 were synthesized from the corresponding cycloalkanones and the various (S)-S-(lithiomethyl)-S-phenylsulfoximine in enantiomerically pure form in yields of 60-70% in a process involving the isomerization of the intermediate vinylic sulfoximines. Desilylation of 26 gave the parent N-H sulfoximine 27 from which the N-sulfonylsulfoximines 28 and 29 were prepared. The X-ray crystal structure of 28 was determined. The allylic sulfoximines 17-20 and 26-29 did not racemize or rearrange thermally to the corresponding allylic sulfinamides. Reaction of the allylic sulfoximines 18, 28, and 29 with the organocuprate reagents 2/LiI, 35/LiI, and 47/LiI led with alpha-selectivities of 92:8 to 99:1 to the endocyclic alkenes 39 in good to high yields. Reaction of 17-20, 28, and 29 with the organocopper reagents 5/LiI, 30/LiI, 31/LiI, 32/LiI, 33/LiI, 34/LiI, and 37/LiI in the presence of BF3 resulted in the formation of the exocyclic alkenes 38, 41, 43, and 45, respectively, in good to high yields with gamma-selectivities of 80:20 to 99:1. The sulfonimidoyl group imparts asymmetric induction to the substitution in the range of 27-90% ee. The (S)-sulfonimidoyl group leads to a preferential bond formation from the si side of the double bond. From the sulfoximines 18 and 26-29 the N-methylsulfoximine 18 and the N-tosylsulfoximine 28 showed the highest and lowest reactivity with the butylcopper reagent 32/LiI in the presence of BF3 respectively, while in the absence of BF3 only 29 reacted. The Lewis acid most likely serves to activate the N-methyl- and N-tosylsulfoximines or intermediates thereof through coordination at the sulfonimidoyl and sulfonyl group. Reaction of the sulfoximines 18 and 29 with pure Me(3)SiCH(2)Cu (34) revealed a strong rate acceleration by LiI and an even stronger one by Bu(4)NI. This points to the existence of a heteroleptic cuprate or a related compound as reactive species. In substitutions with the Yamamoto reagents RCu/MX/BF3, the halide is important and a reaction between RCu and BF3 does not have, at least in the case of allylic sulfoximines, to be invoked. In reactions of 17-20 besides the alkenes, the sulfinamide ent-4 was formed with an ee value of 97% in high yield with retention of configuration. The absolute configuration of the exocyclic alkenes 38, 41, and 45 was determined by ozonolysis to the corresponding cycloalkanones followed by their conversion to the corresponding lactones and/or CD measurement of the former.
• Highly Active Nickel Catalysts for the Isomerization of Unactivated Vinyl Cyclopropanes to Cyclopentenes
  作者：Gang Zuo、Janis Louie

  DOI：10.1002/anie.200353469

  日期：2004.4.19
• Scarpetti, David; Fuchs, Philip L., Journal of the American Chemical Society, 1990, vol. 112, # 22, p. 8084 - 8090
  作者：Scarpetti, David、Fuchs, Philip L.

  DOI：——

  日期：——