(Z)-6-phenylhex-5-en-2-one | 144758-31-6

• 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: (Z)-6-phenylhex-5-en-2-one
• CAS: 144758-31-6
• 化学式: C₁₂H₁₄O
• 分子量: 174.243
• InChiKey: FQAGFMVFSPYMEW-POHAHGRESA-N

物化性质

• 沸点：
  321.5±21.0 °C(Predicted)
• 密度：
  0.984±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (Z)-6-phenylhex-5-en-2-one 在 N-氯代丁二酰亚胺 、 偶氮二异丁腈 、 三正丁基氢锡 、 三乙酰氧基硼氢化钠 、 溶剂黄146 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 7.5h， 生成 5-methyl-2-methylene-1-phenylpyrrolizidine
  参考文献：
  名称：

  Stereoselective synthesis of 2-methylenepyrrolizidines by tandem cyclization of N-propargylaminyl radicals

  摘要：

  Tandem cyclization of N-propargylaminyl radicals, generated by N-chlorination of (E)-alk-4-enylamines 2a-d and 2f followed by treatment with tributyltin radical, afforded 2-methylenepyrrolizidines 3a-d and 3f in a highly stereoselective manner. A similar radical cyclization of (Z)-N-propargyl-1-methyl-5-phenylpent-4-enylamine (2e) gave pyrrolizidine 3b having the same stereochemistry as that obtained from the E isomer 2b. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)01613-7
• 作为产物：
  描述：

  6-苯基-己-5-炔-2-酮 在 Lindlar's catalyst 喹啉 、 氢气 作用下， 以 甲醇 为溶剂， 以94%的产率得到(Z)-6-phenylhex-5-en-2-one
  参考文献：
  名称：

  Stereoselective synthesis of 2-methylenepyrrolizidines by tandem cyclization of N-propargylaminyl radicals

  摘要：

  Tandem cyclization of N-propargylaminyl radicals, generated by N-chlorination of (E)-alk-4-enylamines 2a-d and 2f followed by treatment with tributyltin radical, afforded 2-methylenepyrrolizidines 3a-d and 3f in a highly stereoselective manner. A similar radical cyclization of (Z)-N-propargyl-1-methyl-5-phenylpent-4-enylamine (2e) gave pyrrolizidine 3b having the same stereochemistry as that obtained from the E isomer 2b. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)01613-7

文献信息

• A new approach to organomanganese compounds: the tellurium/manganese exchange reaction
  作者：Márcio S. Silva、João V. Comasseto、Alcindo A. Dos Santos

  DOI：10.1016/j.tetlet.2010.08.005

  日期：2010.10

  Diorganomanganese compounds react with aryl, vinyl, and alkynyl tellurides in a tellurium/manganese exchange reaction. The new mixed organomanganese reagents react selectively with electrophiles.

  二有机锰化合物在碲/锰交换反应中与芳基，乙烯基和炔基碲化物反应。新的混合有机锰试剂与亲电子试剂选择性反应。
• Stereoselective Alkenylation of Activated Olefins via Nickel-Catalyzed Electroreductive Coupling
  作者：Sylvie Condon-Gueugnot、Daniel Dupré、Jean-Yves Nédélec、Jacques Périchon

  DOI：10.1055/s-1997-1371

  日期：1997.12

  The nickel-catalyzed electroreductive conjugate addition of (Z)- or (E)-alkenyl halides to electron-deficient olefins in the presence of a sacrificial iron rod as the anode proceeds with complete retention of the stereochemistry of the alkenyl part and affords functionalized isomerically pure (Z)- or (E)-olefins in high yield.

  在牺牲铁棒作为阳极的情况下，镍催化的（Z）-或（E）-烯基卤化物与缺电子烯烃的电还原共轭加成反应完全保留了烯基部分的立体化学，并提供了官能化的异构体高收率纯(Z)-或(E)-烯烃。
• Nickel-Catalyzed Electrochemical Couplings of Vinyl Halides:  Synthetic and Stereochemical Aspects
  作者：C. Cannes、S. Condon、M. Durandetti、J. Périchon、J.-Y. Nédélec

  DOI：10.1021/jo000182f

  日期：2000.7.1

  Homo- and cross-coupling involving alkenyl halides have been performed efficiently using an electroassisted nickel-complex catalysis. Valuable product such as conjugated dienes, beta,gamma- or gamma,delta-unsaturated esters, ketones, or nitriles, as well as alkenylated aryl compounds are thus prepared with high yields and high stereoselectivity. Partial isomerization is only observed in a few cases, when the alkenyl halide is involved in a late step of the catalytic cycle. This is the case in the preparation of (Z,Z)-1,3-diene.
• Tellurium in Organic Synthesis. Preparation of <i>Z</i>-Vinylic Cuprates from <i>Z</i>-Vinylic Tellurides and Their Reaction with Enones and Epoxides
  作者：Fábio C. Tucci、André Chieffi、João V. Comasseto、Joseph P. Marino

  DOI：10.1021/jo951547c

  日期：1996.1.1

  Z-Vinylic tellurides, obtained with 100% stereoselectivity by the hydrotelluration of acetylenes, are easily transformed into Z-vinylic higher order cyanocuprates by reaction with preformed Me(2)Cu(CN)Li-2, n-Bu(2)Cu(CN)Li-2, or n-Bu(2-Th)Cu(CN)Li-2, with total retention of the double-bond configuration. The resulting vinylic higher order cyanocuprates react with unhindered enones to give the corresponding 1,4-addition products in good yields. Reaction of the vinylic higher order cyanocuprates with monosubstituted epoxides at 0 degrees C gives the homoallylic alcohols resulting from the attack to the less-substituted carbon atom, while the disubstituted epoxides failed to react. Allylic epoxides react at -78 degrees C with the vinylic higher order cyanocuprates to give mixtures of 1,2- and 1,4-opening products, the 1,4-product predominating. In all cases the double-bond configuration of the original vinylic telluride was preserved. The vinylic cuprates derived from simple vinylic tellurides and conjugated 1-telluroenynes react with epoxides at 0 degrees C, while vinylic cuprates derived from conjugated 1-tellurodienes required the addition of 1 equiv of BF3 . Et(2)O to give the homoallylic alcohols on reaction with epoxides. The opening of optically pure epoxides through tellurium/copper transmetalation is stereospecific, giving one single stereoisomer of the corresponding homoallylic alcohol.
• Higher order vinyl cyanocuprates from vinylic tellurides
  作者：Fábio C. Tucci、André Chieffi、João V. Comasseto

  DOI：10.1016/0040-4039(92)89015-5

  日期：1992.9

  Bis-vinylic tellurides, 1-tellurodienes, 1-telluroenynes and vinyl thienyl tellurides react with higher order cyanocuprates giving the corresponding higher order vinyl cyanocuprates with retention of the olefine geometry.