7-phenyl-6-heptenal | 21592-61-0

• 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: 7-phenyl-6-heptenal
• 英文别名: 7-Phenylhept-6-enal；7-phenylhept-6-enal
• CAS: 21592-61-0
• 化学式: C₁₃H₁₆O
• 分子量: 188.269
• InChiKey: RBHRMAROHVKHPB-UHFFFAOYSA-N

物化性质

• 沸点：
  314.9±21.0 °C(Predicted)
• 密度：
  0.971±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  14
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 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：

  7-phenyl-6-heptenal 在 2,6-二甲基吡啶 、 正丁基锂 、 lithium perchlorate 作用下， 以 二氯甲烷 为溶剂， 反应 16.5h， 生成 [(2-Dimethoxymethyl-cyclohexyl)-methoxy-methyl]-benzene
  参考文献：
  名称：

  Intramolecular anodic olefin coupling reactions: a useful method for carbon-carbon bond formation

  摘要：

  The utility of intramolecular anodic olefin coupling reactions for effecting carbon-carbon bond formation has been examined. All of the successful cyclizations studied utilized either an alkyl or silyl enol ether as one of the participating olefins. The enol ethers could be coupled to simple alkyl olefins, styrenes, and allylsilanes in isolated yields ranging from 57 to 84%. The reactions were found to be effective for generating both five- and six-membered rings. The best conditions for cyclization utilized a reticulated vitreous carbon anode, constant-current conditions in an undivided cell, and a lithium perchlorate in either 50% methanol/tetrahydrofuran or 20% methanol/dichloromethane electrolyte solution. The use of an allylsilane as one of the participating olefins allowed for the regiospecific formation of olefinic products. In addition to the olefinic products, these reactions produced a small amount of a cyclized ether product in which the silyl group had not been eliminated. Deuterium-labeling studies showed that at least half of this ether byproduct arose from intramolecular migration of the methoxy group that was initially part of the starting enol ether to the carbon-beta to the silyl group. Intramolecular migration reactions of this type were found to participate in a number of the reported cyclization reactions.

  DOI：

  10.1021/ja00019a038
• 作为产物：
  描述：

  (5-羧基戊基)三苯基溴化磷 在 lithium aluminium tetrahydride 、 草酰氯 、 potassium tert-butylate 、 二甲基亚砜 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 2.67h， 生成 7-phenyl-6-heptenal
  参考文献：
  名称：

  在犬第二代幼虫中与哌酰胺有关的芳烷基和芳烯基酰胺的合成和杀线活性。

  摘要：

  合成了与哌啶相关的79个芳烷基和芳烯基酰胺，并研究了它们对犬round虫Toxocara canis的第二级幼虫的杀线虫活性。活性很大程度上取决于烷基链的长度和胺部分的性质，但是几乎不受链中是否存在双键的影响。在一系列同系物中表现出最强活性的烷基链长，对于吡咯烷酰胺为m = 11，对于N-甲基哌嗪酰胺为m = 13。尽管在所测试的同系物中，哌啶（3，4-亚甲基二氧苯基同系物）显示出最强的活性，但是芳环上的甲氧基取代基对该活性没有太大影响。然而，甲氧基向羟基的转化大大降低了活性并缩短了链长，从而提供了最强的活性。计算出的非酚芳基哌啶的log P值在3.5至4.5范围内，而羟苯基哌啶的log P值较小，表明酚和非酚化合物的杀线活性涉及不同的机理。

  DOI：

  10.1248/cpb.45.685

文献信息

• Crude Drugs Effective on Visceral Larva Migrans. Part XVIII. Synthesis and Nematocidal Activity of Aralkyl- and Aralkenylamides Related to Piperamide on Second-Stage Larvae of Toxocara canis.
  作者：Fumiyuki KIUCHI、Norio NAKAMURA、Makiko SAITOH、Kazue KOMAGOME、Hirokuni HIRAMATSU、Noriaki TAKIMOTO、Nobuaki AKAO、Kaoru KONDO、Yoshisuke TSUDA

  DOI：10.1248/cpb.45.685

  日期：——

  piperamides (3,4-methylenedioxyphenyl homologues) showed the strongest activity among the homologues tested, methoxy substituent(s) on the aromatic ring did not have much effect on the activity. However, conversion of the methoxy group to a hydroxy group greatly decreased the activity and shortened the chain length giving the strongest activity. Calculated log P values of non-phenolic aryl-piperamides fell

  合成了与哌啶相关的79个芳烷基和芳烯基酰胺，并研究了它们对犬round虫Toxocara canis的第二级幼虫的杀线虫活性。活性很大程度上取决于烷基链的长度和胺部分的性质，但是几乎不受链中是否存在双键的影响。在一系列同系物中表现出最强活性的烷基链长，对于吡咯烷酰胺为m = 11，对于N-甲基哌嗪酰胺为m = 13。尽管在所测试的同系物中，哌啶（3，4-亚甲基二氧苯基同系物）显示出最强的活性，但是芳环上的甲氧基取代基对该活性没有太大影响。然而，甲氧基向羟基的转化大大降低了活性并缩短了链长，从而提供了最强的活性。计算出的非酚芳基哌啶的log P值在3.5至4.5范围内，而羟苯基哌啶的log P值较小，表明酚和非酚化合物的杀线活性涉及不同的机理。
• Asymmetric Photolysis of 2-Phenylcycloalkanones with Circularly Polarized Light: A Kinetic Model for Magnetic Field Effects
  作者：Shigeru Kohtani、Masahide Sugiyama、Yoshihisa Fujiwara、Yoshifumi Tanimoto、Ryoichi Nakagaki

  DOI：10.1246/bcsj.75.1223

  日期：2002.6

  (MFE) on asymmetric photolysis involving a biradical intermediate have been investigated on a kinetic model where an intersystem crossing (ISC) of the intermediate is taken into account. Changes in the enantiomeric excesses (ee) of chiral substances with circularly polarized light (CPL) irradiation have been simulated, and the necessary conditions for observing the MFE were obtained. The asymmetric photolysis

  已经在考虑中间体的系统间交叉 (ISC) 的动力学模型上研究了磁场效应 (MFE) 对涉及双自由基中间体的不对称光解。模拟了圆偏振光 (CPL) 照射下手性物质的对映体过量 (ee) 的变化，并获得了观察 MFE 的必要条件。外消旋 2-苯基环烷酮 (2-PCA) 与 CPL 的不对称光解已在存在和不存在磁场的情况下进行。由于 2-PCA 的各向异性 g 因子相当大，尽管未观察到 MFE，但在 90% 分解后，CPL 诱导的 ee 达到了几个百分点。2-PCA 在空气饱和溶液中的光解机理也已阐明。三重酰基-苄基双自由基，通过 2-PCA 的光化学 α-裂解形成，与溶解在溶液中的 O2 反应并导致形成苯乙酮和链烯酸。双分子...
• (Alkynyl)dicobalt Hexacarbonyl-Mediated Radical Cyclizations
  作者：Karen L. Salazar、Kenneth M. Nicholas

  DOI：10.1016/s0040-4020(99)01104-7

  日期：2000.4

  conditions atom transfer products (17a–c, 18c,d) were obtained exclusively, whose regio- and stereochemistry were dependant on the olefinic acceptor. Thus, irradiation of the ester trans-16a or the phenyl derivative 16b (E/Z mixture) gives the trans-cyclopentyl derivatives 17a and 17b; the bromide 16c (R=Me) affords a mixture of the trans-cyclopentyl compound 17c and a comparable amount of the cyclohexyl

  旁侧带有-（炔基）Co 2（CO）6单元的自由基以非常规的立体选择性和区域选择性在分子内添加至碳-碳双键。阳离子络合物13a（R = CO 2 Me）与Zn反应，仅生成反式-5- exo产物14a。由醇7a - d制得的不稳定的炔丙基溴配合物16a - d用Et 3 B / O 2 / Ph 2 SiH 2或在辐射下进行环化。在后一种条件下，原子转移产物（17a– c，18c，d）仅获得，其区域化学和立体化学取决于烯烃受体。因此，该酯的照射反式- 16A或苯基衍生物16B（É / Ž混合物），得到反式-环戊基衍生物17A和17B ; 溴化物16c（R ＝ Me）得到反式-环戊基化合物17c和相当量的环己基衍生物18c的混合物；和母体溴化物16d（R ＝ H）仅转化为环己基衍生物18d。庚烯衍生物20d（R ＝ H）仅环化至7-内环庚基衍生物21d。有限的机械实验表明，自由基链的操作具有类似
• Oxidative Cyclization of Unsaturated Ketene Dithioacetals with Ceric Ammonium Nitrate to Form Bicyclic Lactones
  作者：Barry B Snider、Bo Shi、Cheri A Quickley

  DOI：10.1016/s0040-4020(00)00857-7

  日期：2000.12

  Ceric ammonium nitrate oxidizes unsaturated ketene dithioacetals in wet MeCN to give cation radicals that cyclize to tri-substituted double bonds and styrenes by cation-like cyclizations leading to cyclic cation radicals that are transformed by further oxidation, hydrolysis and cyclization to bicyclic lactones in moderate to good yield. (C) 2000 Elsevier Science Ltd. All rights reserved.
• Synthesis of Cyclic Ketones by Electrochemical Reduction of <i>S</i>-(2-Methoxycarbonyl)phenyl Thiolesters
  作者：Shigeko Ozaki、Hideaki Yoshinaga、Eiki Matsui、Masashi Adachi

  DOI：10.1021/jo001578u

  日期：2001.4.1