(E)-1-chloro-4-(4-chlorobut-2-en-2-yl)benzene | 648425-34-7

• 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)-1-chloro-4-(4-chlorobut-2-en-2-yl)benzene
• 英文别名: 1-chloro-4-[(E)-4-chlorobut-2-en-2-yl]benzene
• CAS: 648425-34-7
• 化学式: C₁₀H₁₀Cl₂
• 分子量: 201.095
• InChiKey: HVRRCXKQUXSJNY-SOFGYWHQSA-N

物化性质

• 沸点：
  284.2±9.0 °C(Predicted)
• 密度：
  1.158±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 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：

  苯丙醛 、 (E)-1-chloro-4-(4-chlorobut-2-en-2-yl)benzene 在 chromium dichloride 、 锰 、 二氯二茂锆 、 3,4,5-trifluoro-N-(2-((S)-4-isopropyl-4,5-dihydrooxazol-2-yl)-6-(((1S,2R,5S)-2-isopropyl-5-methylcyclohexyl)oxy)phenyl)benzenesulfonamide 、 nickel dichloride 、 cesium iodide 作用下， 以 四氢呋喃 为溶剂， 反应 10.0h， 以79%的产率得到(3R,4R)-4-(4-chlorophenyl)-4-methyl-1-phenylhex-5-en-3-ol
  参考文献：
  名称：

  铬催化对映选择性合成四元立体中心

  摘要：

  在磺酰胺/恶唑啉铬配合物的存在下，已经实现了醛与γ-二取代的烯丙基卤的不对称烯丙基化。可以以高度非对映选择性和对映选择性的方式获得具有两个连续的立体生成中心（包括一个季碳）的各种合成上有用的α-均丙醇。

  DOI：

  10.1021/acs.orglett.6b02540
• 作为产物：
  描述：

  (E)-3-(4-chlorophenyl)but-2-en-1-ol 在 甲基磺酰氯 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以90%的产率得到(E)-1-chloro-4-(4-chlorobut-2-en-2-yl)benzene
  参考文献：
  名称：

  Synthesis of novel diazatricyclodecanes (DTDs). Effects of structural variation at the C3′ allyl end and at the phenyl ring of the cinnamyl chain on μ-receptor affinity and opioid antinociception

  摘要：

  Two series of analogues of 9-propionyl-10-cinnamyl-9,10-diazatricyclo[4.2.1.1(2,5)]decane (1a) and 2-propionyl-7-cinnamyl-2,7-diazatricyclo[4.4.0.0(3,8)]decane (2a), in which the cinnamyl moiety was replaced by various aralkenyl chains, 1b-1 and 2b-1, respectively, have been synthesized and evaluated for their ability to bind to the opioid mu-, delta- and kappa-receptors. The binding data indicated that compounds 1b,d,e,h and 2b,d,e,f,h,i showed a mu-affinity in the low nanomolar range with moderate or negligible affinity towards delta- and kappa-receptors. Selected DTDs, the pairs 1,2b,1,2e and 1,2h, were also evaluated for analgesic effect. In the hot plate test, only 1b given ip was found to have similar opioid antinociception and chronic tolerance as morphine. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(03)00373-0

文献信息

• Synthesis, biological evaluation and docking studies of a novel class of sulfur-bridged diazabicyclo[3.3.1]nonanes
  作者：Gabriele Murineddu、Battistina Asproni、Paola Corona、Stefania Gessi、Stefania Merighi、Enrica Battistello、Chiara Sturaro、Girolamo Calò、Nicoletta Galeotti、Veronika Temml、Sonja Herdlinger、Daniela Schuster、Gerard A. Pinna

  DOI：10.1016/j.bioorg.2020.104072

  日期：2020.9

  A small library of 3-thia-7,9-diazabicyclo[3.3.1]nonanes was synthesized and their opioid receptors affinity and selectivity evaluated. Among these novel sulfur-bridged compounds, the (E) 9-[3′-(3-chlorophenyl)-but-2′-en-1′-yl]-7-propionyl-3-thia-7,9-diazabicyclo[3.3.1]nonane 2i emerged as the derivative with the highest μ receptor affinity (Ki = 85 nM) and selectivity (Ki μ/δ = 58.8, Ki μ/κ > 117

  合成了3-thia-7,9-diazabicyclo [3.3.1]壬烷的小文库，并评估了其阿片受体的亲和力和选择性。在这些新颖的硫桥化合物中，（E）9- [3'-（3-氯苯基）-but-2'-en-1'-基] -7-丙酰基-3-thia-7,9-二氮杂双环[3.3.1]壬烷2I成为该衍生物具有最高μ受体的亲和力（ķ我 = 85 nM）的和选择性（ķ我μ/ δ  = 58.8，ķ我μ/κ> 117.6）。在急性热痛中还评估了2i的抗伤害感受活性。对接研究揭示了这些衍生物相互作用的具体模式。
• Enantioselective Synthesis of Quaternary Stereocenters via Chromium Catalysis
  作者：Yang Xiong、Guozhu Zhang

  DOI：10.1021/acs.orglett.6b02540

  日期：2016.10.7

  of a sulfonamide/oxazoline chromium complex. A variety of synthetically useful α-homoallylic alcohols with two consecutive stereogenic centers, including one quaternary carbon, can be accessed in a highly diastereoselective and enantioselective manner.

  在磺酰胺/恶唑啉铬配合物的存在下，已经实现了醛与γ-二取代的烯丙基卤的不对称烯丙基化。可以以高度非对映选择性和对映选择性的方式获得具有两个连续的立体生成中心（包括一个季碳）的各种合成上有用的α-均丙醇。
• Synthesis of novel diazatricyclodecanes (DTDs). Effects of structural variation at the C3′ allyl end and at the phenyl ring of the cinnamyl chain on μ-receptor affinity and opioid antinociception
  作者：Gérard Aimè Pinna、Giorgio Cignarella、Stefania Ruiu、Giovanni Loriga、Gabriele Murineddu、Stefania Villa、Giuseppe Enrico Grella、Gregorio Cossu、Walter Fratta

  DOI：10.1016/s0968-0896(03)00373-0

  日期：2003.9

  Two series of analogues of 9-propionyl-10-cinnamyl-9,10-diazatricyclo[4.2.1.1(2,5)]decane (1a) and 2-propionyl-7-cinnamyl-2,7-diazatricyclo[4.4.0.0(3,8)]decane (2a), in which the cinnamyl moiety was replaced by various aralkenyl chains, 1b-1 and 2b-1, respectively, have been synthesized and evaluated for their ability to bind to the opioid mu-, delta- and kappa-receptors. The binding data indicated that compounds 1b,d,e,h and 2b,d,e,f,h,i showed a mu-affinity in the low nanomolar range with moderate or negligible affinity towards delta- and kappa-receptors. Selected DTDs, the pairs 1,2b,1,2e and 1,2h, were also evaluated for analgesic effect. In the hot plate test, only 1b given ip was found to have similar opioid antinociception and chronic tolerance as morphine. (C) 2003 Elsevier Ltd. All rights reserved.