methyl 2,2-dichloro-3-hydroxy-5-phenylpent-4(E)-enoate | 507231-47-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂醇
• 英文名称: methyl 2,2-dichloro-3-hydroxy-5-phenylpent-4(E)-enoate
• 英文别名: 2,2-dichloro-3-hydroxy-5-phenyl-pent-4-enoic acid methyl ester；methyl (E)-2,2-dichloro-3-hydroxy-5-phenylpent-4-enoate
• CAS: 507231-47-2
• 化学式: C₁₂H₁₂Cl₂O₃
• 分子量: 275.131
• InChiKey: FIICNEREECDBPP-BQYQJAHWSA-N

物化性质

• 沸点：
  439.7±45.0 °C(Predicted)
• 密度：
  1.347±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl 2,2-dichloro-3-hydroxy-5-phenylpent-4(E)-enoate 在 chromium dichloride 作用下， 以 四氢呋喃 为溶剂， 生成 methyl 2-chloro-5-phenylpent-2(Z),4(E)-dienoate
  参考文献：
  名称：

  (Z)-α-Haloacrylates:  An Exceptionally Stereoselective Preparation via Cr(II)-Mediated Olefination of Aldehydes with Trihaloacetates

  摘要：

  (Z)-alpha-Fluoro-, (Z)-alpha-chloro-, and (Z)-alpha-bromoacrylates were obtained with unprecedented yield and stereocontrol (>99%) via addition of the corresponding commercial trihaloacetates to aldehydes at room temperature using stoichiometric Cr(II) salts or catalytic Cr(II) with a regeneration system. The intermediate 2,2-dihalo-3-hydroxy adducts could be isolated in good yields under conditions of limited reagent at 0 degrees C.

  DOI：

  10.1021/ja029938d
• 作为产物：
  描述：

  三氯乙酸甲酯 、 肉桂醛 在 chromium dichloride 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 以78%的产率得到methyl 2,2-dichloro-3-hydroxy-5-phenylpent-4(E)-enoate
  参考文献：
  名称：

  (Z)-α-Haloacrylates:  An Exceptionally Stereoselective Preparation via Cr(II)-Mediated Olefination of Aldehydes with Trihaloacetates

  摘要：

  (Z)-alpha-Fluoro-, (Z)-alpha-chloro-, and (Z)-alpha-bromoacrylates were obtained with unprecedented yield and stereocontrol (>99%) via addition of the corresponding commercial trihaloacetates to aldehydes at room temperature using stoichiometric Cr(II) salts or catalytic Cr(II) with a regeneration system. The intermediate 2,2-dihalo-3-hydroxy adducts could be isolated in good yields under conditions of limited reagent at 0 degrees C.

  DOI：

  10.1021/ja029938d

文献信息

• Synthesis of dihalohydrins and tri- and tetra-substituted olefins
  申请人：Board of Regents, The University of Texas System

  公开号：US20040143125A1

  公开（公告）日：2004-07-22

  A novel synthesis reaction for highly stereospecific tri- and tetra-substituted olefins is described. A single stereoisomer of stable &agr;-halo-&agr;,&bgr;-ester is produced in high yield by the reaction of aldehyde or ketone with a trihalogenated compound such as trichloroacetate in the presence of CrCl 2 in a solvent. By varying the amount of CrCl 2 used, the stable dihalohydrin intermediate may be obtained as well.

  描述了一种用于高度立体特异性三取代和四取代烯烃的新合成反应。通过醛或酮与三卤代化合物（如三氯乙酸盐）在溶剂中在CrCl2存在下的反应，可以高产率地产生稳定的α-卤代-α，β-酯的单立体异构体。通过改变使用的CrCl2量，也可以获得稳定的二卤水合物中间体。
• Synthesis of ( Z )-α-chloro-α,β-unsaturated esters with complete stereoselectivity promoted by samarium diiodide
  作者：José M. Concellón、Mónica Huerta、Ricardo Llavona

  DOI：10.1016/j.tetlet.2004.04.101

  日期：2004.6

  Stereoselective beta-elimination in alpha,alpha-dichloro-beta-hydroxyesters 2 was achieved by using samarium diiodide, yielding (Z)-alpha-chloro-alpha, beta-unsaturated esters 1. The starting compounds 2 were easily prepared by reaction of the lithium enolate of ethyl dichloroacetate with different aldehydes at -78 degreesC. A mechanism to explain this process is proposed. (C) 2004 Elsevier Ltd. All rights reserved.
• US7084281B2
  申请人：——

  公开号：US7084281B2

  公开（公告）日：2006-08-01
• (<i>Z</i>)-α-Haloacrylates:  An Exceptionally Stereoselective Preparation via Cr(II)-Mediated Olefination of Aldehydes with Trihaloacetates
  作者：D. K. Barma、Abhijit Kundu、Hongming Zhang、Charles Mioskowski、J. R. Falck

  DOI：10.1021/ja029938d

  日期：2003.3.1

  (Z)-alpha-Fluoro-, (Z)-alpha-chloro-, and (Z)-alpha-bromoacrylates were obtained with unprecedented yield and stereocontrol (>99%) via addition of the corresponding commercial trihaloacetates to aldehydes at room temperature using stoichiometric Cr(II) salts or catalytic Cr(II) with a regeneration system. The intermediate 2,2-dihalo-3-hydroxy adducts could be isolated in good yields under conditions of limited reagent at 0 degrees C.