2-chloro-1,3-diphenyl-prop-2-en-1-ol | 130996-38-2

• 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: 2-chloro-1,3-diphenyl-prop-2-en-1-ol
• 英文别名: (Z)-2-chloro-1,3-diphenylprop-2-en-1-ol
• CAS: 130996-38-2
• 化学式: C₁₅H₁₃ClO
• 分子量: 244.721
• InChiKey: PBJKOUPPWNUIFK-KAMYIIQDSA-N

物化性质

• 沸点：
  392.9±30.0 °C(Predicted)
• 密度：
  1.220±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  17
• 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：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-chloro-1,3-diphenyl-prop-2-en-1-ol 在 乙烯双(三苯基磷)铂 、 三乙胺 作用下， 以 四氢呋喃 、 乙醚 、 氘代氯仿 为溶剂， 反应 8.5h， 生成
  参考文献：
  名称：

  A New Platinum Complex Catalyzed Reaction Involving Nucleophilic Substitution at the Central Carbon Atom of the π-Allyl Ligand

  摘要：

  The reaction of 2-chloro-allyl acetate with sodium ethyl acetoacetate in the presence of a platinum(O) complex gave furan derivatives. The key feature of this-new platinum-catalyzed reaction is the nucleophilic substitution at the central carbon atom of pi-allyl complexes. The regioselectivity of the nucleophilic attacks (central or terminal) is dependent on the pK(a) of the nucleophile. In addition, a labeling experiment revealed that a rapid syn-anti isomerization of the (pi-allyl) platinum complexes occurs.

  DOI：

  10.1021/jo990845x
• 作为产物：
  描述：

  1,1,1-三氯-2-苯基乙烷 、 苯甲醛 在 chromium dichloride 作用下， 以 四氢呋喃 为溶剂， 以82%的产率得到2-chloro-1,3-diphenyl-prop-2-en-1-ol
  参考文献：
  名称：

  Chromium Vinylidene Carbenoids:  Stereospecific Synthesis of (Z)-2-Chloroalk-2-en-1-ols

  摘要：

  [GRAPHICS](Z)-2-Chloroalk-2-en-1-ols are obtained in excellent yields from a wide variety of aldehydes by addition of (E)-chromium vinylidene carbenoids, stereospecifically generated from trichloroalkanes using CrCl2 in THF at room temperature.

  DOI：

  10.1021/ol016935h

文献信息

• Visible Light‐Enabled sp ³ ‐C−H Functionalization with Chloro‐ and Bromoalkynes: Chemoselective Route to Vinylchlorides or Alkynes
  作者：Tapas Adak、Marvin Hoffmann、Sina Witzel、Matthias Rudolph、Andreas Dreuw、A. Stephen K. Hashmi

  DOI：10.1002/chem.202001259

  日期：2020.12

  valuable vinyl chlorides. The photo‐organocatalytic hydrogen atom transfer strategy gives rise to a broad range of diversely functionalized olefins. When bromoalkynes are applied in the presence of a base, a chemoselectivity switch to an alkynylation is observed. This reaction can even be performed for the alkynylation of unactivated sp3‐C−H bonds, in this case with a preference of the more substituted

  实现了氯炔的前所未有的直接原子经济化学和区域选择性加氢烷基化和溴炔的 sp 3 -C-H 炔基化。反应伙伴是未官能化的醚、醇、酰胺，甚至未活化的烃。我们发现家用荧光灯能够激发二芳基酮，然后二芳基酮选择性地从 sp 3 ‐C−H 键中提取 H 原子。用氯炔获得正式炔插入 sp 3 ‐C−H 键的产物，从而提供有价值的氯乙烯。光有机催化氢原子转移策略产生了多种不同官能化的烯烃。当在碱存在下应用溴代炔时，观察到化学选择性转变为炔基化。该反应甚至可以用于未活化的 sp 3 -C-H 键的炔基化，在这种情况下优选取代更多的碳。伴随的量子化学计算表明乙烯基自由基中间体与碳自由基中心具有明显的线性配位，从而能够在H原子抽象后形成两种非对映异构体，表明( Z )-非对映异构体是优选的，这支持了实验观察到的( E / Z )‐分布。
• A versatile synthesis of 2-haloalk-2(Z)-en-1-ols and 1-chloro-1(Z)-alkenes from trichloromethylcarbinols
  作者：Rachid Baati、D.K Barma、J.R Falck、Charles Mioskowski

  DOI：10.1016/s0040-4039(02)00210-1

  日期：2002.3

  CrCl2 converts trichloromethylcarbinols under mild conditions to (E)-alpha-haloalkylidene chromium carbenoids which add to aldehydes or are quenched with water affording 2-haloalk-2(Z)-en-1-ols and 1-chloro-1(Z)-alkenes, respectively, in high yield. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Chromium Vinylidene Carbenoids:  Generation, Characterization, and Reactivity. First Evidence for an Internal Proton Return Phenomenon with Vinylidene Carbenoids
  作者：Rachid Baati、D. K. Barma、J. R. Falck、C. Mioskowski

  DOI：10.1021/ja016515n

  日期：2001.9.1
• Three-component synthesis of 2-haloalk-2(Z)-en-1-ols via tandem haloalkylidenation–aldehyde addition
  作者：Rachid Baati、D.K. Barma、J.R. Falck、Charles Mioskowski

  DOI：10.1016/s0040-4039(02)00206-x

  日期：2002.3

  Cr(II)-induced condensation of CCl4 or CBr4 with an aldehyde stereospecifically generates an (E)-alpha-haloalkylidene chromium carbenoid which adds in situ to a second equivalent of aldehyde furnishing 2-haloalk-2(Z)-en-1-ols in high yield. (C) 2002 Elsevier Science Ltd. All rights reserved.