(E)-7-(phenylsulfonyl)-6-hepten-7-al | 107010-56-0

• 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: (E)-7-(phenylsulfonyl)-6-hepten-7-al
• 英文别名: (E)-7-(phenylsulfonyl)hept-6-enal；(E)-7-(benzenesulfonyl)hept-6-enal
• CAS: 107010-56-0
• 化学式: C₁₃H₁₆O₃S
• 分子量: 252.334
• InChiKey: MKOZZGGZOHETHA-XYOKQWHBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  59.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-7-(phenylsulfonyl)-6-hepten-7-al 在 4-二甲氨基吡啶 、 四(三苯基膦)钯 吡啶 、 臭氧 、 magnesium 、 1,2-双(二苯基膦)乙烷 作用下， 生成 cis-octahydro-1H-inden-1-one
  参考文献：
  名称：

  An intramolecular carbocyclic [3 + 2] cycloaddition via organopalladium intermediates

  摘要：

  DOI：

  10.1021/ja00377a038
• 作为产物：
  描述：

  2-[6-(phenylsulfonyl)hex-5-enyl]-[1,3]dithiane 在 calcium carbonate 、 碘甲烷 作用下， 以 水 、 乙腈 为溶剂， 反应 3.0h， 以90%的产率得到(E)-7-(phenylsulfonyl)-6-hepten-7-al
  参考文献：
  名称：

  Organocatalyst-mediated enantioselective intramolecular Michael addition of aldehydes to vinyl sulfones

  摘要：

  Chiral amines with a hydrogen bond donor promote the intramolecular conjugate addition of aldehydes to vinyl sulfones. Chiral cyclic sulfone-aldehydes are obtained in good yields with an ee of up to 82%. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.03.043

文献信息

• Stereoselective ring opening reaction of 2-[(phenylthio)methyl]cycloalkanols mediated by N-chlorosuccinimide and triethylamine
  作者：Ken Takaki、Masateru Yasumura、Takao Tamura、Kenji Negoro

  DOI：10.1021/jo00383a015

  日期：1987.4
• Intramolecular palladium-catalyzed trimethylenemethane cycloadditions: initial studies
  作者：Barry M. Trost、Timothy A. Grese、Dominic M. T. Chan

  DOI：10.1021/ja00019a036

  日期：1991.9

  The potential application of [3 + 2] cycloadditions to polycarbocycle construction is considerably enhanced by the ability to perform such reactions intramolecularly. The feasibility of such processes is explored in the context of Pd-catalyzed cycloadditions of 2-[(trimethylsilyl)methyl]allyl carboxylates, wherein trimethylenemethane (TMM) precursor fragment (donor) and the electron-deficient olefin (acceptor) is joined by a tether of simple methylene groups of 3, 4, 5, and 8 members. Several versatile synthetic routes to these substrates were developed. 2-Bromo-3-(trimethylsilyl)propene proves to be a key reagent for construction of the donor portion. Acceptors bearing esters, cyano groups, and especially sulfones have been examined. The diastereoselectivity of the reaction has been explored both in terms of ring juncture and the diastereofacial selectivity with respect to an oxygen substituent at the allylic position of the acceptor. Excellent cycloadditions to give the bicyclo[3.3.0] octyl and bicyclo[4.3.0]nonyl systems are observed, whereas larger rings cannot be obtained in this series. The choice of catalyst proves critical, the most useful being either tetrakis(triphenylphosphine)palladium and DPPE or, more generally, triisopropyl phosphite and palladium acetate. The first cycloaddition of a 1,1-dialkylated TMM precursor, which fails in intermolecular cases, has been observed in this intramolecular series to give a bridgehead-substituted bicycle. A rationale for the observed diastereoselectivity is presented.
• TROST, B. M.;CHAN, D. M. T., J. AMER. CHEM. SOC., 1982, 104, N 13, 3733-3735
  作者：TROST, B. M.、CHAN, D. M. T.

  DOI：——

  日期：——
• Organocatalyst-mediated enantioselective intramolecular Michael addition of aldehydes to vinyl sulfones
  作者：Chloée Bournaud、Estelle Marchal、Adrien Quintard、Sarah Sulzer-Mossé、Alexandre Alexakis

  DOI：10.1016/j.tetasy.2010.03.043

  日期：2010.7

  Chiral amines with a hydrogen bond donor promote the intramolecular conjugate addition of aldehydes to vinyl sulfones. Chiral cyclic sulfone-aldehydes are obtained in good yields with an ee of up to 82%. (C) 2010 Elsevier Ltd. All rights reserved.
• An intramolecular carbocyclic [3 + 2] cycloaddition via organopalladium intermediates
  作者：Barry M. Trost、Dominic M. T. Chan

  DOI：10.1021/ja00377a038

  日期：1982.6