1-Chloro-1,3-diphenylprop-2-ene | 121441-07-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 1-Chloro-1,3-diphenylprop-2-ene
• 英文别名: 3-Chloro-1,3-diphenylpropene；1,3-diphenylallyl chloride；(E)-1,3-diphenyl-3-chloroprop-1-ene；[(E)-1-chloro-3-phenylprop-2-enyl]benzene
• CAS: 121441-07-4
• 化学式: C₁₅H₁₃Cl
• 分子量: 228.721
• InChiKey: LTYVUIWHQHZJCE-VAWYXSNFSA-N

物化性质

• 沸点：
  343.9±11.0 °C(Predicted)
• 密度：
  1.125±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  1-Chloro-1,3-diphenylprop-2-ene 在 吡啶 、 四丁基氟化铵 、 四丁基溴化铵 、 二正丁基氧化锡 作用下， 以 四氢呋喃 为溶剂， 生成 4,6-Di-O-benzoyl-3-O-(1,3-diphenylprop-2-en-1-yl)-D-glucal
  参考文献：
  名称：

  The stereospecific synthesis of methyl α-C-mannobioside: a potential inhibitor of M. tuberculosis binding to human macrophages

  摘要：

  The synthesis of the C-glycoside analogue of the mycobacteria capping disaccharide, Man alpha 1-2Man, employing a glycosyl organosamarium is described.

  DOI：

  10.1039/cc9960001661
• 作为产物：
  描述：

  反-1,3-二苯基-2-丙稀-1-醇 在 氯化亚砜 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以99%的产率得到1-Chloro-1,3-diphenylprop-2-ene
  参考文献：
  名称：

  (1,3-二苯基烯丙基)二甲基锍离子的二甲基硫醚交换动力学

  摘要：

  通过变温1 H NMR 光谱研究了 CD 2 Cl 2中 (1,3-二苯基烯丙基) 二甲基锍离子的烯丙基重排动力学，该重排通过中间体 1,3-二苯基烯丙基阳离子进行。在低温下，三个烯丙基质子产生 AMX 系统，两个非对映体S-甲基基团以不同的频率共振。在较高温度下，观察到烯丙基质子的 AX 2系统和S-甲基基团的单一信号。所得汇率常数为 (364 ± 2) s –1在 25°C，对应于 C-S 键的异裂速率，用于探索线性自由能关系 log k het (25°C) =  s f ( N f  +  E f ），它描述了由电离参数E f和溶剂相关的离核剂特定参数N f和s f引起的异裂速率。观察到的速率常数证实了先前的结论，即两组不同的N f和s f相同的nucleofuge 可能存在参数。了解反向成键反应是在活化下还是在扩散控制下发生对于选择适当的核逸散性参数集至关重要。

  DOI：

  10.1002/poc.4270

文献信息

• Electrophilicities of Symmetrically Substituted 1,3-Diarylallyl Cations
  作者：Konstantin Troshin、Claus Schindele、Herbert Mayr

  DOI：10.1021/jo201668w

  日期：2011.11.18

  Kinetics of the reactions of nine symmetrically substituted 1,3-diarylallyl cations with different nucleophiles were studied photometrically in dichloromethane, acetonitrile, and DMSO solutions. The second-order rate constants k2 were found to follow the correlation log k2 = sN(N + E). The electrophilicity parameters E of the title cations were derived, using the known values of sN and N of the nucleophilic

  在二氯甲烷，乙腈和DMSO溶液中，以光度法研究了9个对称取代的1,3-二芳基烯丙基阳离子与不同亲核试剂的反应动力学。发现二阶速率常数k 2遵循相关对数k 2＝s N（N + E）。使用亲核反应伙伴的s N和N的已知值，得出标题阳离子的亲电参数E，并将其与类似取代的苯甲基铵离子的亲电性进行比较。在亲电性之间发现良好的线性相关性E和烯丙基阳离子的量子化学计算的气相甲基阴离子亲和力和取代基X的σ +常数。
• BIOCATALYST FOR CATALYTIC HYDROAMINATION
  申请人：Hauer Bernhard

  公开号：US20120123155A1

  公开（公告）日：2012-05-17

  The present invention relates to a method for the enzymatic hydroamination of C—C double bonds catalyzed by enzymes structurally and/or functionally related to phenylalanine ammonia lyase (PAL) isolated from microorganisms of Petroselinum crispum, Rhodoturula glutinis and/or functional active derivatives thereof.

  本发明涉及一种由与从欧芹、红曹霉等微生物中分离的结构和/或功能上与苯丙氨酸氨基裂解酶（PAL）相关的酶催化的C—C双键的酶促水氨化方法。
• Laser Flash, Laser-Drop, and Lamp Photolysis of 1,3-Dichloro-1,3-diphenylpropane. One- <i>versus</i> Two-Photon Reaction Pathways
  作者：Miguel Angel Miranda、Julia Pérez-Prieto、Enrique Font-Sanchis、Klára Kónya、J. C. Scaiano

  DOI：10.1021/jo9704772

  日期：1997.8.1

  Low intensity irradiation of 1,3-dichloro-1,3-diphenylpropane (1) in cyclohexane leads to the formation of 3-chloro-1,3-diphenylpropyl radical (2) through homolytic C-CI bond cleavage. Radical 2 gives rise to final products typical of free radical reactions. Neither 1,2-diphenylcyclopropanes (6) nor 3-cyclohexyl-1,3-diphenylpropene (20) are obtained under these conditions. Nevertheless, high intensity laser irradiation of the initially formed monoradical 2 leads to the 1,3-diphenylpropenyl radical (3) detected with nanosecond techniques. This intermediate is completely trapped by the cyclohexyl radicals generated in the medium to yield 20. Photolysis of 1 with the laser-drop technique leads to the cyclopropanes 6 as major photoproducts.
• Asymmetric synthesis catalyzed by chiral ferrocenylphosphine - transition-metal complexes. 8. Palladium-catalyzed asymmetric allylic amination
  作者：Tamio Hayashi、Akihiro Yamamoto、Yoshihiko Ito、Eriko Nishioka、Hitoshi Miura、Kazunori Yanagi

  DOI：10.1021/ja00198a048

  日期：1989.8
• Samarium Diiodide PromotedC-Glycosylation: An Application to the Stereospecific Synthesis ofα-1,2-C-Mannobioside and Its Derivatives
  作者：Olivier Jarreton、Troels Skrydstrup、Juan-Félix Espinosa、Jesús Jiménez-Barbero、Jean-Marie Beau

  DOI：10.1002/(sici)1521-3765(19990201)5:2<430::aid-chem430>3.0.co;2-d

  日期：1999.2.1

  The synthesis of the C-glycoside analogue of the disaccharide Man(alpha 1-->2)Man has been achieved in a highly stereoselective and efficient manner employing an approach which closely parallels O-glycoside synthesis. The key step included the samarium diiodide reduction of mannosyl pyridylsulfone 18 in the presence of the C2-formyl branched mannoside derivative 17a to furnish the C-disaccharide derivative 19a in high yield. An intramolecular formyl group transfer reaction by means of 5-exo radical cyclization and concomitant fragmentation yielded aldehyde 17a stereospecifically. We also present a potentially viable alternative for the deoxygenation of sterically encumbered secondary alcohols. Attempts to extend this procedure to the synthesis of the C-trisaccharide of Man(alpha 1-->2)Man(alpha 1-->2)Man were frustrated by the inability of the disaccharide, pyridylsulfone derivative 43, to undergo coupling with carbonyl substrates upon treatment with SmI2, possibly owing to the sterically bulky C2 substituent.