(3-氯-1-苯基丙-1-烯基)苯 | 24626-27-5

• 物质功能分类: 化学试剂 - 有机试剂 - 烯烃（环状与无环状）
• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: (3-氯-1-苯基丙-1-烯基)苯
• 英文名称: 3,3-diphenylallyl chloride
• 英文别名: 3,3-diphenylprop-2-enyl chloride；(3-chloroprop-1-ene-1,1-diyl)dibenzene；1,1-Diphenyl-3-chlor-propen-(1)；1,1-diphenyl-3-chloro-1-propene；3-Chloro-1,1-diphenylpropene；(3-chloro-1-phenylprop-1-enyl)benzene
• CAS: 24626-27-5
• 化学式: C₁₅H₁₃Cl
• 分子量: 228.721
• InChiKey: MTOVXZPDHLKNAO-UHFFFAOYSA-N

物化性质

• 沸点：
  159-161 °C(Press: 4 Torr)
• 密度：
  1.098±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.36
• 重原子数：
  16.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  0.0

反应信息

• 作为反应物：
  描述：

  (3-氯-1-苯基丙-1-烯基)苯 以59%的产率得到
  参考文献：
  名称：

  HIRABE, TOMOATSU;NOJIMA, MASATOMO;KUSABAYASHI, SHIGEKAZU, J. ORG. CHEM., 1984, 49, N 21, 4084-4086

  摘要：

  DOI：
• 作为产物：
  描述：

  ethyl 3,3-diphenylacrylate 在 二异丁基氢化铝 、 三乙胺 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 1.0h， 生成 (3-氯-1-苯基丙-1-烯基)苯
  参考文献：
  名称：

  N-3(9)-Arylpropenyl-N-9(3)-propionyl-3,9-diazabicyclo[3.3.1]nonanes as μ-Opioid receptor agonists. Effects on μ-Affinity of arylalkenyl chain modifications

  摘要：

  Two series of N-3-arylpropenyl-N-9-propionyl-3,9-diazabicyclo[3.3.1]nonanes (1b-j) and of the reverted N-3-propionyl-N-9-arylpropenyl isomers (2b-j) as analogues of the previously reported analgesic N-3(9)-cinnamyl-N-9(3)-propionyl-3,9-diazabicyclo[3.3.1]nonanes (DBN) (1a, 2a) were synthesised and their affinity and selectivity towards opioid mu-, delta- and K-receptors were evaluated. Several compounds (1e,i.j 2d,e,f,g,j) exhibited a p-affinity in the low nanomolar range with moderate or negligible affinity towards delta- and kappa-receptors. The representative term N-9-(3,3-diphonylprop-2-enyl)-N-3-propionyl-DBN (2d) displayed in vivo (mouse) a potent analgesic effect (ED50 3.88 mg/kg ip) which favourably compared with that of morphine (ED50 5 mg/kg ip). In addition, 2d produced in mice tolerance after a period twice as long with morphine. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(01)00436-9

文献信息

• Anti-inflammatory and analgesic 3-hydroxybenzo[b]thiophene derivatives,
  申请人：Merck & Co., Inc.

  公开号：US04663344A1

  公开（公告）日：1987-05-05

  3-Hydroxybenzo[b]thiophene derivatives, such as 2-aralkyl, 2-alkyl and 2-alkenyl-3-hydroxybenzo[b]-thiophenes, were prepared by, among other methods, ring closure of 2-(2-carboxy-phenylthio)-.alpha.-substituted acetic acids. These compounds are found to be useful in the treatment of pain, fever, inflammation, arthritic conditions, asthma, allergic disorders, skin diseases, cardiovascular disorders, psoriasis, inflammatory diseases and other prostaglandin and/or leukotriene mediated diseases.

  3-羟基苯并[b]噻吩衍生物，如2-芳基、2-烷基和2-烯基-3-羟基苯并[b]噻吩，可通过多种方法制备，其中包括2-(2-羧基苯硫基)-α-取代乙酸的环闭合。这些化合物被发现在治疗疼痛、发热、炎症、关节炎、哮喘、过敏性疾病、皮肤病、心血管疾病、牛皮癣、炎症性疾病和其他前列腺素和/或白三烯介导的疾病中具有用处。
• Direct Conversion of Aldehydes and Ketones to Allylic Halides by a NbX5-[3,3] Rearrangement
  作者：Fraser Fleming、P. Ravikumar、Lihua Yao

  DOI：10.1055/s-0028-1088222

  日期：2009.4

  bromide and NbCl(5), or NbBr(5), to a series of aldehydes and ketones directly provides homologated, allylic halides. Transposition of the intermediate vinyl alkoxide is envisaged through a metalla-halo-[3,3] rearrangement with concomitant delivery of the halogen to the terminal carbon. The [3,3] rearrangement is equally effective for the conversion of a propargyllic alcohol to the corresponding allenyl

  将乙烯基溴化镁和 NbC​​l(5) 或 NbBr(5) 依次添加到一系列醛和酮中，可直接提供同系的烯丙基卤化物。中间体乙烯基醇盐的转位是通过金属卤代-[3,3] 重排与卤素同时传递到末端碳来实现的。[3,3] 重排对于将炔丙醇转化为相应的烯基溴同样有效。
• Allylic and Allenic Halide Synthesis via NbCl₅- and NbBr₅-Mediated Alkoxide Rearrangements
  作者：P. C. Ravikumar、Lihua Yao、Fraser F. Fleming

  DOI：10.1021/jo901287f

  日期：2009.10.2

  Addition of NbCl5 or NbBr5 to a series of magnesium, lithium, or potassium allylic or propargylic alkoxides directly provides allylic or allenic halides. Halogenation formally occurs through a metalla-halo-[3,3] rearrangement, although concerted, ionic, and direct displacement mechanisms appear to operate competitively. Transposition of the olefin is equally effective for allylic alkoxides prepared

  将NbCl 5或 NbBr 5 添加到一系列镁、锂或钾的烯丙基或炔丙基醇盐中直接提供烯丙基或烯丙基卤化物。卤化通过金属-卤-[3,3] 重排正式发生，尽管协同、离子和直接置换机制似乎具有竞争性。烯烃的转位对于通过亲核加成、去质子化或还原制备的烯丙基醇盐同样有效。实验上，五卤化铌卤化反应迅速，萃取后可提供基本纯的 ( E )-烯丙基或烯丙基卤化物，适用于一系列脂肪族和芳香族醇、醛和酮。
• Photocatalyzed Diastereoselective Isomerization of Cinnamyl Chlorides to Cyclopropanes
  作者：Bin Xu、Ludovic Troian-Gautier、Ryan Dykstra、Robert T. Martin、Osvaldo Gutierrez、Uttam K. Tambar

  DOI：10.1021/jacs.0c00147

  日期：2020.4.1

  Endergonic isomerizations are thermodynamically unfavored processes that are difficult to realize under thermal conditions. We report a photocatalytic diastereoselective isomerization of acyclic cinnamyl chlorides to strained cyclopropanes. Quantum mechanical calculations (uM06-2X and DLPNO), including TD-DFT calculations, and experimental studies provide evidence for the energy transfer from an iridium

  Endergonic 异构化是热力学上不利的过程，在热条件下难以实现。我们报告了无环肉桂酰氯到应变环丙烷的光催化非对映选择性异构化。量子力学计算（uM06-2X 和 DLPNO），包括 TD-DFT 计算和实验研究为能量从铱光催化剂转移到烯丙基氯化物底物，然后是 C-Cl 均裂提供了证据。随后的 Cl• 自由基迁移形成局部三重 1,3-双自由基中间体，在系统间交叉后，进行闭环以形成所需的产物。温和的反应条件与广泛的官能团兼容，以高产率和非对映选择性生成氯环丙烷。通过添加催化量的镍络合物开发了一种更有效的工艺，我们提出了这种助催化剂的新作用，以回收反应过程中产生的烯丙基氯副产物。该反应也显示为立体收敛的，因为肉桂酰氯的 E/Z 混合物以高非对映选择性提供抗氯环丙烷产物。我们预计，使用可见光活化的光催化剂转化底物与过渡金属催化剂相结合，将副产物循环回催化循环，将为发现新的反应性提供独特的机会。
• A Novel One-Pot Conversion of Allyl Alcohols into Primary Allyl Halides Mediated by Acetyl Halide
  作者：Nurhan Kishali、M. Fatih Polat、Ramazan Altundas、Yunus Kara

  DOI：10.1002/hlca.200890014

  日期：2008.1

  primary allyl chlorides and bromides 9–16 from the secondary or tertiary allyl alcohols 3–8 and acyl halide was developed (Scheme 2, Table 1). Non-commercially available secondary and tertiary allyl alcohols were synthesized from the related ketones and aldehydes via the addition of vinylmagnesium chloride. Mechanistic studies indicate that the alcohols were first acetylated by the acetyl halide and then

  用于主烯丙基氯化物和溴化物的合成的新且简单的方法9 - 16从仲或叔烯丙基醇3 - 8和酰基卤被开发（方案2，表1）。通过添加乙烯基氯化镁，从相关的酮和醛合成了非市售的仲和叔烯丙醇。机制研究表明，醇被首先由乙酰卤乙酰化，然后由卤化物，氯取代前质子化-或Br - ，经由一个小号Ñ 2'反应，得到初级卤化物（方案5）。