(Z)-2-iodohex-2-enoic acid ethyl ester | 478555-84-9

• 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: (Z)-2-iodohex-2-enoic acid ethyl ester
• 英文别名: 2-iodo-hex-2-enoic acid ethyl ester；(Z)-ethyl 2-iodohex-2-enoate；ethyl (Z)-2-iodo-2-hexenoate；ethyl (Z)-2-iodohex-2-enoate
• CAS: 478555-84-9
• 化学式: C₈H₁₃IO₂
• 分子量: 268.095
• InChiKey: GNIIOPZUPLWWQX-SREVYHEPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  11
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.62
• 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：

  N-Boc-L-cysteine ethyl ester 、 (Z)-2-iodohex-2-enoic acid ethyl ester 在 tris(dibenzylideneacetone)dipalladium(0) chloroform complex 1,1'-双(二苯基膦)二茂铁 、 三乙胺 作用下， 以 N-甲基吡咯烷酮 为溶剂， 反应 3.0h， 以70%的产率得到(Z)-2-((2'R)-2'-(tert-butoxycarbonyl)amino-2'-(ethoxycarbonyl)ethylsulfanyl)hex-2-enoic acid ethyl ester
  参考文献：
  名称：

  半胱氨酸衍生物与芳基和烯基卤化物的钯催化硫醇交叉偶联

  摘要：

  已经研究了钯催化的半胱氨酸硫醇与芳基和乙烯基卤化物的交叉偶联反应：Pd 2 dba 3 -CHCl 3和dppf是这些反应的关键选择。碱在这些反应中的作用也受到质疑：已经证明碱可以被HX清除剂（例如环氧丙烷）代替。

  DOI：

  10.1016/s0022-328x(03)00635-1
• 作为产物：
  描述：

  在 碘 、 potassium carbonate 作用下， 以 甲苯 为溶剂， 反应 10.0h， 以62%的产率得到(Z)-2-iodohex-2-enoic acid ethyl ester
  参考文献：
  名称：

  Iodo Meyer–Schuster Rearrangement of 3-Alkoxy-2-yn-1-ols for β-Mono (Exclusively Z-Selective)-/Disubstituted α-Iodo-α,β-Unsaturated Esters

  摘要：

  We herein present the iodo Meyer-Schuster rearrangement of 3-alkoxypropargyl alcohols for α-iodo-α,β-unsaturated esters using iodine or NIS in dichloromethane at ambient temperature. Substrates prepared from both aldehydes and ketones are found to be equally good feedstock for the reaction to produce β-mono- and -disubstituted products. Irrespective of the substitution, substrates prepared from aldehydes gave Z-isomers exclusively.

  DOI：

  10.1021/ol502224s

文献信息

• Approaches toward the Total Synthesis of the Nine-Membered Thio-Lactone Core of Griseoviridin
  作者：Xavier Moreau、Jean-Marc Campagne

  DOI：10.1021/jo034195f

  日期：2003.6.1

  toward the synthesis of the macrocyclic thiolactone core of griseoviridin have been studied. Intramolecular palladium-catalyzed thiol coupling and esterification (carboxylate activation) have led to the formation of unexpected rearranged products. An intermolecular palladium-catalyzed thiol/vinyl iodide coupling followed by an esterification (alcohol activation) ultimately led to the nine-membered

  已经研究了三种合成灰黄绿异丁烯的大环硫代内酯核心的方法。分子内钯催化的硫醇偶联和酯化（羧酸酯活化）导致形成意想不到的重排产物。分子间钯催化的硫醇/碘化乙烯偶联，然后进行酯化（酒精活化），最终导致灰黄霉素的九元核心。
• α-Hypervalent Iodine Functionalized Phosphonium and Arsonium Ylides and Their Tandem Reaction as Umpolung Reagents
  作者：Zhizhen Huang、Xiaochun Yu、Xian Huang

  DOI：10.1021/jo026077i

  日期：2002.11.1

  iodine functionalized phosphonium and arsonium ylides 2 can be used as umpolung ylides to react with nucleophiles to give alpha-heteroatom substituted ylides 4 in good yields. The nucleophilic substitution-Wittig tandem reaction of 2 can occur smoothly to provide an efficient method for the synthesis of (Z)-alpha-halo-alpha,beta-unsaturated enoates or enones 6, stereoselectively.

  可以将α-高价碘官能化的nium和son的叶立德2用作化合物基的叶立德与亲核试剂反应，以高收率得到α-杂原子取代的叶立德4。2的亲核取代-维蒂希串联反应可以顺利进行，从而为立体选择性地合成（Z）-α-卤代-α，β-不饱和烯酸酯或烯酮6提供了一种有效的方法。
• Iodo Meyer–Schuster Rearrangement of 3-Alkoxy-2-yn-1-ols for β-Mono (Exclusively Z-Selective)-/Disubstituted α-Iodo-α,β-Unsaturated Esters
  作者：Surendra Puri、Nuligonda Thirupathi、Maddi Sridhar Reddy

  DOI：10.1021/ol502224s

  日期：2014.10.17

  We herein present the iodo Meyer-Schuster rearrangement of 3-alkoxypropargyl alcohols for α-iodo-α,β-unsaturated esters using iodine or NIS in dichloromethane at ambient temperature. Substrates prepared from both aldehydes and ketones are found to be equally good feedstock for the reaction to produce β-mono- and -disubstituted products. Irrespective of the substitution, substrates prepared from aldehydes gave Z-isomers exclusively.
• Palladium catalyzed thiol cross-coupling of cystein derivatives with aryl and alkenyl halides
  作者：Xavier Moreau、Jean-Marc Campagne

  DOI：10.1016/s0022-328x(03)00635-1

  日期：2003.12

  Palladium catalyzed cystein thiol cross-coupling reactions with aryl and vinyl halides have been investigated: Pd2dba3-CHCl3 and dppf are the key choice in these reactions. The role of the base in these reactions was also questioned: it has been shown that base can be replaced by an HX-scavenger such as propylene oxide.

  已经研究了钯催化的半胱氨酸硫醇与芳基和乙烯基卤化物的交叉偶联反应：Pd 2 dba 3 -CHCl 3和dppf是这些反应的关键选择。碱在这些反应中的作用也受到质疑：已经证明碱可以被HX清除剂（例如环氧丙烷）代替。