2-chloro-4-phenyl-pent-2-enoic acid methyl ester | 507231-36-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 2-chloro-4-phenyl-pent-2-enoic acid methyl ester
• 英文别名: methyl 2-chloro-4-phenyl-pent-2(Z)-enoate；methyl 2-chloro-4-phenylpent-2(Z)-enoate；methyl (Z)-2-chloro-4-phenylpent-2-enoate
• CAS: 507231-36-9
• 化学式: C₁₂H₁₃ClO₂
• 分子量: 224.687
• InChiKey: RBJDPVMVIHNAHH-FLIBITNWSA-N

物化性质

• 沸点：
  309.7±30.0 °C(Predicted)
• 密度：
  1.138±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-chloro-4-phenyl-pent-2-enoic acid methyl ester 在 吡啶 、 lithium hydroxide 、 氯化亚砜 、 N,N-二甲基甲酰胺 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 19.0h， 生成 N-(2-carbomethoxyphenyl)-2-chloro-4-(phenyl)-pent-2(Z)-enamide
  参考文献：
  名称：

  Inhibition of telomerase by BIBR 1532 and related analogues

  摘要：

  BIBR 1532 has been reported to be a potent, small molecule inhibitor of human telomerase, suggesting it as a lead for the development of anti-telomerase therapy. We confirm the ability of BIBR 1532 to inhibit telomerase and report the discovery of an equally potent analogue. Importantly, IC50 values in cell extract are considerably higher than those previously reported using assays for purified enzyme, indicating that substantial improvement may be necessary. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00101-x
• 作为产物：
  描述：

  2,2-dichloro-3-hydroxy-4-phenyl-pentanoic acid methyl ester 在 samarium diiodide 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以68%的产率得到2-chloro-4-phenyl-pent-2-enoic acid methyl ester
  参考文献：
  名称：

  Synthesis of ( Z )-α-chloro-α,β-unsaturated esters with complete stereoselectivity promoted by samarium diiodide

  摘要：

  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.

  DOI：

  10.1016/j.tetlet.2004.04.101

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。
• (<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.
• US7084281B2
  申请人：——

  公开号：US7084281B2

  公开（公告）日：2006-08-01
• 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.
• Inhibition of telomerase by BIBR 1532 and related analogues
  作者：D.K Barma、Anissa Elayadi、J.R Falck、David R Corey

  DOI：10.1016/s0960-894x(03)00101-x

  日期：2003.4

  BIBR 1532 has been reported to be a potent, small molecule inhibitor of human telomerase, suggesting it as a lead for the development of anti-telomerase therapy. We confirm the ability of BIBR 1532 to inhibit telomerase and report the discovery of an equally potent analogue. Importantly, IC50 values in cell extract are considerably higher than those previously reported using assays for purified enzyme, indicating that substantial improvement may be necessary. (C) 2003 Elsevier Science Ltd. All rights reserved.