(+)-(R_S)-5-<(4-Methylphenyl)sulfinyl>pent-1-ene | 118558-73-9

• 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: (+)-(R_S)-5-<(4-Methylphenyl)sulfinyl>pent-1-ene
• 英文别名: (R_S)-5-<(4-Methylphenyl)sulfinyl>pent-1-ene；5-<(4-methylphenyl)sulfinyl>pent-1-ene；(+)-(R_S)-5-[(4-Methylphenyl)sulfinyl]pent-1-ene；1-methyl-4-[(R)-pent-4-enylsulfinyl]benzene
• CAS: 118558-73-9
• 化学式: C₁₂H₁₆OS
• 分子量: 208.324
• InChiKey: AEVUFBOXIRMJTE-CQSZACIVSA-N

物化性质

• 沸点：
  339.7±31.0 °C(Predicted)
• 密度：
  1.07±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  36.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (+)-(R_S)-5-<(4-Methylphenyl)sulfinyl>pent-1-ene 在 4-二甲氨基吡啶 、 sodium hydroxide 、 二异丁基氢化铝 、 N,N'-二环己基碳二亚胺 、 三氟乙酸酐 、 sodium iodide 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 二氯甲烷 、 丙酮 为溶剂， 反应 1.58h， 生成 (R)-2-Phenyl-propionic acid (1R,2R)-1-(chloro-fluoro-methyl)-2-p-tolylsulfanyl-hex-5-enyl ester
  参考文献：
  名称：

  氟化亚砜-Chiron路线合成光学纯的单氟环己醇衍生物

  摘要：

  Monofluorocyclohexanols 1是光学纯形式通过偕- chlorofluoroheptenols的自由基环化得到2从亚砜的α -锂衍生物的缩合得到3上外消旋乙基chlorofluoroacetate 4，和氢化促进的还原中间体酮5。自由基促进环化反应的立体化学过程的一些考虑如下。

  DOI：

  10.1016/s0040-4020(01)89545-4
• 作为产物：
  描述：

  (-)-menthyl p-toluenesulfinate 、 5-溴-1-戊烯 在 magnesium 作用下， 生成 (+)-(R_S)-5-<(4-Methylphenyl)sulfinyl>pent-1-ene
  参考文献：
  名称：

  Synthesis of Enantiomerically Pure gem-Difluorocyclohexane Derivatives by Intramolecular Trapping of .alpha.,.alpha.-Difluoroalkyl Radicals

  摘要：

  gem-Difluorocyclohexanols 7 and 16 bearing, respectively, the arylsulfinyl and the arylthio substituent are obtained by radical-promoted cyclization from the corresponding omega-chlorodifluoroheptenols 6 and 9 in good yields. Intermediates 6 are made available by condensing the lithium derivative of chiral arylsulfinyl pentene 4 on ethyl chlorodifluoroacetate and by reducing the carbonyl with hydride-releasing agents. Elimination of the chiral auxiliary sulfinyl group and appropriate elaborations afford enantiomerically pure alpha-hydroxy-, alpha-hydroxy-Delta 3,4-, alpha,beta,gamma-trihydroxy-, and alpha-hydroxy-beta,gamma-epoxy-gem-difluorocyclohexane derivatives 19, 21, 22, and 23. Absolute and relative configurations as well as preferred conformations in solution are given. The degree of asymmetric induction during the radical-promoted cyclization is correlated with the relative configuration of substituted carbons in open-chain compounds.

  DOI：

  10.1021/jo00091a041

文献信息

• Stereoselective Synthesis of Trifluoro- and Monofluoro-Analogues of Frontalin and Evaluation of Their Biological Activity
  作者：Paolo Ambrosi、Alberto Arnone、Pierfrancesco Bravo、Luca Bruché、Antonio De Cristofaro、Valeria Francardi、Massimo Frigerio、Enzo Gatti、Giacinto S. Germinara、Walter Panzeri、Fabrizio Pennacchio、Cristina Pesenti、Giuseppe Rotundo、Pio F. Roversi、Cristina Salvadori、Fiorenza Viani、Matteo Zanda

  DOI：10.1021/jo0055640

  日期：2001.12.1

  stereoselective synthesis of both enantiomers of trifluoro frontalin (-)-(1S,5R)- and (+)-(1R,5S)-8, as well as of diastereomeric monofluoro frontalines (-)-(1R,2R,5R)-18 and (-)-(1R,2S,5R)-20, analogues of the bioactive component of the aggregation pheromone of the Scolytidae insect family, has been accomplished starting from (-)-(1R)- and (+)-(1S)-menthyl (S)-toluene-4-sulfinate as a source of chirality and

  立体选择性合成三氟额叶蛋白（-）-（1S，5R）-和（+）-（1R，5S）-8的对映异构体以及非对映体单氟额叶碱（-）-（1R，2R，5R） -18和（-）-（1R，2S，5R）-20是鞘翅目昆虫家族聚集信息素生物活性成分的类似物，从（-）-（1R）-和（+）- （1S）-薄荷基（S）-甲苯-4-亚磺酸盐作为手性来源，三氟乙酸甲酯或氟乙酸甲酯分别作为氟来源。C-1立体中心是通过重氮甲烷将β-亚磺酰基酮2和13进行立体选择性环氧化而安装的。双环核是通过完全立体控制和化学选择性串联的Wacker氧化/中间不饱和亚磺酰基二醇5、15和19的分子内缩酮化而获得的。在实验室测试中，轴向氟化（-）-20引发了对Dendroctonus micans雌性女性的强电响应，而赤道氟化（-）-18和三氟类似物（-）-8则显示了适度的响应。由于（D）micans局部稀少，使用（-）-20进行的田间试验没有指示性，但对其他鞘翅目科显示出一定的吸引力。
• Bravo, Pierfrancesco; Ganazzoli, Fabio; Resnati, Giuseppe, Journal of Chemical Research, Miniprint, 1988, # 7, p. 1701 - 1739
  作者：Bravo, Pierfrancesco、Ganazzoli, Fabio、Resnati, Giuseppe、Munari, Sergio De、Albinati, Alberto

  DOI：——

  日期：——
• Bravo, Pierfrancesco; Piovosi, Elena; Resnati, Giuseppe, Gazzetta Chimica Italiana, 1988, vol. 118, # 2, p. 115 - 122
  作者：Bravo, Pierfrancesco、Piovosi, Elena、Resnati, Giuseppe、Munari, Sergio De

  DOI：——

  日期：——
• Synthesis of Enantiomerically Pure Fluoro- and gem-Chlorofluorocyclohexane Derivatives
  作者：Alberto Arnone、Pierfrancesco Bravo、Massimo Frigerio、Fiorenza Viani、Giancarlo Cavicchio、Marcello Crucianelli

  DOI：10.1021/jo00100a057

  日期：1994.10

  gem-Chloronuorocyclohexanols 10 are prepared in good yields by radical-promoted cyclization from the corresponding omega-dichlorofluoroheptenols 4. Fluorocyclohexanols 11 are obtained either from 10 or in a single step from open-chain alcohols 4. The stereochemical outcome of both the radical cyclization and the reductive dechlorination is discussed. Elimination of the chiral auxiliary sulfinyl group and appropriate elaborations afford enantiomerically pure derivatives 12-17. Relative and absolute configurations as well as preferred conformations in solution for all final compounds are provided.
• BRAVO, PIERFRANCESCO;PIOVOSI, ELENA;RESNATI, GIUSEPPE;DE, MUNARI SERGIO, GAZZ. CHIM. ITAL., 118,(1988) N 2, 115-122
  作者：BRAVO, PIERFRANCESCO、PIOVOSI, ELENA、RESNATI, GIUSEPPE、DE, MUNARI SERGIO

  DOI：——

  日期：——