3-Phenyl-pent-4-enoyl chloride | 137586-02-8

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物
• 英文名称: 3-Phenyl-pent-4-enoyl chloride
• 英文别名: 3-phenylpent-4-enoyl chloride
• CAS: 137586-02-8
• 化学式: C₁₁H₁₁ClO
• 分子量: 194.661
• InChiKey: NMENBRIUZNIOKC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.11
• 重原子数：
  13.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  17.07
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  3-Phenyl-pent-4-enoyl chloride 在 Liver acetone powder 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 (R)-(+)-3-phenyl-4-pentenoic acid ethyl ester
  参考文献：
  名称：

  The studies on chemoenzymatic synthesis of Femoxetine

  摘要：

  The studies on enzymatic kinetic resolution of 3-phenyl-4-pentenoic acid esters were performed. The obtained results demonstrated that the careful choice of biocatalyst and a reaction type are very important for successful enzymatic kinetic resolution. Kinetic resolution provides 3-phenyl-4-pentenoic acid (1) with good enantioselectivity upon esterification. That product was used as a substrate for formal synthesis of two biologically relevant compounds Femoxetine and LG 121071. (C) 2012 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcatb.2012.06.009
• 作为产物：
  描述：

  ethyl 3-phenyl-4-pentenoate 在 sodium hydroxide 、 草酰氯 作用下， 生成 3-Phenyl-pent-4-enoyl chloride
  参考文献：
  名称：

  Inversion of the Direction of Stereoinduction in the Coupling of Chiral γ,δ-Unsaturated Fischer Carbene Complexes with o-Ethynylbenzaldehyde

  摘要：

  [GRAPHICS]A variety of gamma,delta-unsaturated carbene complexes that feature a stereogenic center at the beta-carbon couple with 2-ethynylbenzaldehyde to afford hydrophenanthrene derivatives with a high degree of stereoinduction. The direction of stereoinduction is opposite for examples where the stereogenic center is acyclic vs examples where it is within a ring.

  DOI：

  10.1021/ol025808y

文献信息

• Stereoselectivity in amidyl radical cyclisations. Acyl mode cyclisations
  作者：Andrew J Clark、Joanne L Peacock

  DOI：10.1016/s0040-4039(98)01189-7

  日期：1998.8

  Amidyl radicals generated from tributylstannane mediated homolysis of O-benzoyl hydroxamic acid derivatives undergo 5-exo cyclisation to give mixtures of cis and trans pyrrolidinones. While the steric nature of the nitrogen substituents investigated had little effect on the diastereoselectivity of the process they did effect the relative rate of the cyclisation reactions. The major products could be

  由三丁基锡烷介导的O-苯甲酰基异羟肟酸衍生物的均化作用生成的酰胺基进行5-exo环化，生成顺式和反式吡咯烷酮的混合物。尽管所研究的氮取代基的空间性质对该方法的非对映选择性几乎没有影响，但它们确实影响环化反应的相对速率。可以通过应用“贝克威法则”来预测主要产品。
• Synthesis and reactions of iodo lactams
  作者：Spencer Knapp、Anthony T. Levorse

  DOI：10.1021/jo00252a024

  日期：1988.8
• 5-Deoxy-5-alkyl-1,2-O-isopropylidene-α-D-xylofuranoses as chiral auxiliaries in asymmetric 1,4-addition reaction
  作者：Yung-Son Hon、Fen-Ling Chen、Yih-Pyng Huang、Ta-Jung Lu

  DOI：10.1016/s0957-4166(00)82200-4

  日期：1991.1

  Two deoxy-sugar based chiral auxiliaries (2 and 5) have been prepared. Their alpha,beta-unsaturated esters were treated with different cuprate reagents to give the 1,4-addition adducts in good chemical yield and good diastereoselectivity.