(E)-3-iodo-2-butenamide | 307492-61-1

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 乙烯基卤化物
• 英文名称: (E)-3-iodo-2-butenamide
• 英文别名: (E)-3-iodobut-2-enamide
• CAS: 307492-61-1
• 化学式: C₄H₆INO
• 分子量: 211.002
• InChiKey: AIHBQHGOZNEONE-NSCUHMNNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  7
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  43.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  ((3S,4R,5S,6S,E)-3,5-Dimethoxy-4,6-dimethyloct-1-en-7-yn-1-yl)benzene 、 (E)-3-iodo-2-butenamide 在 bis-triphenylphosphine-palladium(II) chloride 、 三正丁基氢锡 作用下， 以 四氢呋喃 为溶剂， 反应 0.25h， 以73%的产率得到(+)-crocacin C
  参考文献：
  名称：

  Total Synthesis of (+)-Crocacin C Using Hidden Symmetry

  摘要：

  A highly convergent and protecting-group-free synthesis of (+)-crocacin C, featuring an enzymatic enantioselective desymmetrization of a meso-diol, a base-induced ring opening of a THP ring, and a one-pot hydrostannylation/Stille coupling as the key steps, is reported. The natural product was obtained in 11 steps and 22.3% overall yield starting from readily available oxabicycle 1. Finally, a unique enantioselective step, an enzymatic desymmetrization, revealed four stereogenic centers and created one in C4 of the THP furnishing the dense building block 4 with high enantioselectivity (ce >98%).

  DOI：

  10.1021/jo902582w
• 作为产物：
  描述：

  (E)-3-iodobut-2-enoic acid methyl ester 在 三甲基铝 、 氯化铵 作用下， 以 甲苯 为溶剂， 反应 16.0h， 以52%的产率得到(E)-3-iodo-2-butenamide
  参考文献：
  名称：

  （+）-crocacin C的全合成

  摘要：

  遵循收敛策略，实现了光学纯形式的（+）-crocacin C（3）的首次合成。合成还建立了这种新型的有效抗真菌和高细胞毒性化合物的绝对立体化学。天然存在的卡洛卡因C具有（6 S，7 S，8 R，9 S）构型，对于该家族的其他同类产品，卡洛卡星A，B和D也是相同的。

  DOI：

  10.1016/s0040-4039(00)02002-5

文献信息

• Total synthesis of (+)-crocacin C
  作者：Tushar K Chakraborty、Sarva Jayaprakash

  DOI：10.1016/s0040-4039(00)02002-5

  日期：2001.1

  The first synthesis of (+)-crocacin C (3) in optically pure form is achieved following a convergent strategy. The synthesis also establishes the absolute stereochemistries of this novel class of potent antifungal and highly cytotoxic compounds. The naturally occurring crocacin C has (6S,7S,8R,9S) configuration, which is also the same for other congeners of the family, crocacins A, B and D.

  遵循收敛策略，实现了光学纯形式的（+）-crocacin C（3）的首次合成。合成还建立了这种新型的有效抗真菌和高细胞毒性化合物的绝对立体化学。天然存在的卡洛卡因C具有（6 S，7 S，8 R，9 S）构型，对于该家族的其他同类产品，卡洛卡星A，B和D也是相同的。
• Enantioselective Synthesis of (+)-Crocacin C. An Example of a Highly Challenging Mismatched Double Asymmetric δ-Stannylcrotylboration Reaction
  作者：Ming Chen、William R. Roush

  DOI：10.1021/ol300476f

  日期：2012.4.6

  A concise, enantioselective synthesis of (+)-crocacin C is described, featuring a highly diastereoselective mismatched double asymmetric delta-stannylcrotylboration of the stereochemically demanding chiral aldehyde 9 with the bifunctional crotylborane reagent (S)-E-10. The total synthesis of (+)-crocacin C was accomplished in seven steps (longest linear sequence) starting from commercially available precursors.
• Asymmetric total synthesis of the myxobacteria metabolites crocacins A–D
  作者：John T. Feutrill、Michael J. Lilly、Jonathan M. White、Mark A. Rizzacasa

  DOI：10.1016/j.tet.2008.01.139

  日期：2008.5

  The total syntheses of crocacins A-D are described. The key steps were a syn-aldol reaction followed by anti-reduction to secure the stereo-tetrad and acylation of an ene- or dienecarbamate to form the enamide. Crown Copyright (C) 2008 Published by Elsevier Ltd. All rights reserved.
• Total Synthesis of (+)-Crocacin C Using Hidden Symmetry
  作者：Mathieu Candy、Gérard Audran、Hugues Bienaymé、Cyril Bressy、Jean-Marc Pons

  DOI：10.1021/jo902582w

  日期：2010.3.5

  A highly convergent and protecting-group-free synthesis of (+)-crocacin C, featuring an enzymatic enantioselective desymmetrization of a meso-diol, a base-induced ring opening of a THP ring, and a one-pot hydrostannylation/Stille coupling as the key steps, is reported. The natural product was obtained in 11 steps and 22.3% overall yield starting from readily available oxabicycle 1. Finally, a unique enantioselective step, an enzymatic desymmetrization, revealed four stereogenic centers and created one in C4 of the THP furnishing the dense building block 4 with high enantioselectivity (ce >98%).
• Step-Economic Synthesis of (+)-Crocacin C: A Concise Crotylboronation/[3,3]-Sigmatropic Rearrangement Approach
  作者：Adele E. Pasqua、Frank D. Ferrari、Chris Hamman、Yanzhou Liu、James J. Crawford、Rodolfo Marquez

  DOI：10.1021/jo301210f

  日期：2012.8.17

  The step-economic total synthesis of (+)-crocacin C has been achieved in 20% yield from commercially available starting materials. This approach requires the isolation of only 8 intermediates and can provide a reliable supply of (+)-crocacin C for the development of new antifungal and crop protection agents.