tert-butyl 3-(2-iodophenyl)acrylate | 1073950-76-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: tert-butyl 3-(2-iodophenyl)acrylate
• 英文别名: tert-butyl 3-(2-iodophenyl)prop-2-enoate
• CAS: 1073950-76-1
• 化学式: C₁₃H₁₅IO₂
• 分子量: 330.165
• InChiKey: SAVSVRYSBVALNH-UHFFFAOYSA-N

物化性质

• 沸点：
  357.8±25.0 °C(Predicted)
• 密度：
  1.486±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.65
• 重原子数：
  16.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  tert-butyl 3-(2-iodophenyl)acrylate 、 (S)-(-)-N-苄基-1-苯基-乙胺 在 正丁基锂 、 水 、 氯化铵 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 2.5h， 以96%的产率得到(3R,αS)-tert-butyl 3-(N-benzyl-N-α-methylbenzylamino)-3-(2-iodophenyl)propanoate
  参考文献：
  名称：

  Asymmetric synthesis of syn- and anti-α-deuterio-β3-phenylalanine derivatives

  摘要：

  The conjugate addition of lithium (S)-N-benzyl-N-(alpha-methylbenzyl)amide to a range of aryl substituted tert-butyl cinnamate esters followed by reaction of the resultant lithium beta-amino enolates with D2O provides access to anti configured alpha-deuterio-beta-aminocinnamate esters in high dr. The corresponding syn configured diastereoisomers were also obtained with high diastereoselectivity via the conjugate addition of lithium (5)-N-benzyl-N-(alpha-methylbenzyl)amide to a range of tert-butyl alpha-deuteriocinnamate esters followed by reaction of the resultant lithium beta-amino enolates with 2-pyridone. After deprotection both the syn- and anti-diastereoisomers of the corresponding alpha-deuterio-beta(3)-amino acids can be isolated in high dr. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2011.06.008

文献信息

• Regioselective Synthesis of <i>N</i>-Aminoisoindolones and Mono-<i>N</i>- and Di-<i>N,N</i>′-substituted Phthalazones Utilizing Hydrazine Nucleophiles in a Palladium-Catalyzed Three-Component Cascade Process
  作者：Ronald Grigg、Visuvanathar Sridharan、Mufakhrul Shah、Simon Mutton、Colin Kilner、David MacPherson、Peter Milner

  DOI：10.1021/jo800822p

  日期：2008.11.7

  A palladium-catalyzed three-component cascade process for the synthesis of isoindolone and phthalazone derivatives is reported. The cascade process involves carbonylation of an aryl iodide/Michael acceptor to give an acylpalladium species which is intercepted by a hydrazine nucleophile. Intramolecular Michael addition follows to give either N-aminoisoindolones or mono- N- and di-N,N'-phthalazones depending

  报道了钯催化的三组分级联方法，用于合成异吲哚酮和酞菁衍生物。级联过程涉及芳基碘/迈克尔受体的羰基化，以得到酰基肼类物质，其被肼亲核试剂拦截。取决于是否使用单取代或1，2-二取代的肼亲核试剂，分子内迈克尔加成随后给出N-氨基异吲哚酮或单-N-和二-N，N'-邻苯二氮酮。
• Synthesis of Functionalized Indanes via Palladium-Catalyzed Carboannulation of Diazabicyclic Olefins with o-Iodostyrenes
  作者：Kokkuvayil Radhakrishnan、Eliyan Jijy、Praveen Prakash、Shreyass Saranya、Eringathodi Suresh

  DOI：10.1055/s-0033-1338507

  日期：——

  Palladium-catalyzed carboannulation of bicyclic and tricyclic hydrazines with substituted o-iodostyrenes produced functionalized indanes in good to excellent yields. The methodology provides an important carbocyclic ring system under relatively mild conditions.