benzyl (E)-4-chloro-4-oxobut-2-enoate | 55656-55-8

• 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: benzyl (E)-4-chloro-4-oxobut-2-enoate
• 英文别名: benzyl (E)-4-chloro-4-oxo-2-butenoate
• CAS: 55656-55-8
• 化学式: C₁₁H₉ClO₃
• 分子量: 224.644
• InChiKey: KSZVJNXMLSFSNA-VOTSOKGWSA-N

物化性质

• 沸点：
  330.2±25.0 °C(Predicted)
• 密度：
  1.266±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.05
• 重原子数：
  15.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  43.37
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  benzyl (E)-4-chloro-4-oxobut-2-enoate 、 (2R)-bornane-10,2-sultam 在 sodium hydride 作用下， 生成 (-)-(2R)-N-<(E)-3-<(benzyloxy)carbonyl>prop-2-enoyl>bornane-10,2-sultam
  参考文献：
  名称：

  Stereoselectivity in the TiCl4-Catalyzed [4+2] Cycloaddition of Cyclopentadiene to (2R)-Bornane-10,2-sultam Derivatives of Fumaric Acid Monoesters

  摘要：

  The [4 + 2] cycloaddition of cyclopentadiene to the (2R)-bornane-10,2-sultam derivative (-)-1b of fumaric monomethyl ester proceeds with high endo and pi-facial diastereoselectivity in the presence of 0.5 mol-equiv. of TiCl4. The major diastereoisomer endo-(2R,3R)-2b, isolated in 87% yield by crystallization, was subjected to X-ray crystal-structure analysis. Steric influence of ethyl- and benzyl-ester analogues (-)-1c and (-)-1d, respectively, is also reported.

  DOI：

  10.1002/(sici)1522-2675(19990210)82:2<182::aid-hlca182>3.0.co;2-p
• 作为产物：
  描述：

  Benzyl fumarate 在 草酰氯 作用下， 生成 benzyl (E)-4-chloro-4-oxobut-2-enoate
  参考文献：
  名称：

  Stereoselectivity in the TiCl4-Catalyzed [4+2] Cycloaddition of Cyclopentadiene to (2R)-Bornane-10,2-sultam Derivatives of Fumaric Acid Monoesters

  摘要：

  The [4 + 2] cycloaddition of cyclopentadiene to the (2R)-bornane-10,2-sultam derivative (-)-1b of fumaric monomethyl ester proceeds with high endo and pi-facial diastereoselectivity in the presence of 0.5 mol-equiv. of TiCl4. The major diastereoisomer endo-(2R,3R)-2b, isolated in 87% yield by crystallization, was subjected to X-ray crystal-structure analysis. Steric influence of ethyl- and benzyl-ester analogues (-)-1c and (-)-1d, respectively, is also reported.

  DOI：

  10.1002/(sici)1522-2675(19990210)82:2<182::aid-hlca182>3.0.co;2-p

文献信息

• Irreversible blockage of opioid receptor types by ester homologs of .beta.-funaltrexamine
  作者：J. W. Schoenecker、A. E. Takemori、P. S. Portoghese

  DOI：10.1021/jm00160a013

  日期：1986.10

  A series of ester homologues 2-5 of the mu receptor nonequilibrium antagonist beta-funaltrexamine (1, beta-FNA) was synthesized. These ligands were of interest in our investigation of the relationship between the structure of the ester function and the ability to irreversibly block mu opioid receptors. While all of the ligands were potent reversible agonists in the guinea pig ileum (GPI) and mouse vas deferens (MVD) preparations, most appeared to behave as irreversible antagonists of morphine. The benzyl 5 and phenethyl 6 esters possessed irreversible mu antagonist potency that was of similar magnitude to that of beta-FNA in the GPI. In the MVD, all esters appeared to irreversibly block the agonist effect of morphine, but none of the compounds irreversibly antagonized [D-Ala2,D-Leu5]enkephalin to a significant degree. [3H]Dihydromorphine displacement studies revealed no relationship between the affinity of the esters 1-6 and the irreversible blockage of mu receptors in the GPI or MVD. Possible reasons for the observed structure-activity relationship are discussed.
• Stereoselectivity in the TiCl4-Catalyzed [4+2] Cycloaddition of Cyclopentadiene to (2R)-Bornane-10,2-sultam Derivatives of Fumaric Acid Monoesters
  作者：Michal Achmatowicz、Christian Chapuis、Piotr Rzepecki、Janusz Jurczak

  DOI：10.1002/(sici)1522-2675(19990210)82:2<182::aid-hlca182>3.0.co;2-p

  日期：1999.2.10

  The [4 + 2] cycloaddition of cyclopentadiene to the (2R)-bornane-10,2-sultam derivative (-)-1b of fumaric monomethyl ester proceeds with high endo and pi-facial diastereoselectivity in the presence of 0.5 mol-equiv. of TiCl4. The major diastereoisomer endo-(2R,3R)-2b, isolated in 87% yield by crystallization, was subjected to X-ray crystal-structure analysis. Steric influence of ethyl- and benzyl-ester analogues (-)-1c and (-)-1d, respectively, is also reported.