(4R,5R,E)-2,2,2-trichloroethyl 4-(benzyloxy)-6,6,6-trifluoro-5-(methoxymethylenoxy)hex-2-enoate | 1000881-38-8

• 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: (4R,5R,E)-2,2,2-trichloroethyl 4-(benzyloxy)-6,6,6-trifluoro-5-(methoxymethylenoxy)hex-2-enoate
• 英文别名: 2,2,2-trichloroethyl (E,4R,5R)-6,6,6-trifluoro-5-(methoxymethoxy)-4-phenylmethoxyhex-2-enoate
• CAS: 1000881-38-8
• 化学式: C₁₇H₁₈Cl₃F₃O₅
• 分子量: 465.681
• InChiKey: HLGJLFWZENFDRK-KHGFPJFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  28
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (4R,5R,E)-2,2,2-trichloroethyl 4-(benzyloxy)-6,6,6-trifluoro-5-(methoxymethylenoxy)hex-2-enoate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 以95%的产率得到(4R,5R,E)-2,2,2-trichloroethyl 4-(benzyloxy)-6,6,6-trifluoro-5-hydroxyhex-2-enoate
  参考文献：
  名称：

  Total synthesis of trifluoromethylated analogs of macrosphelide A

  摘要：

  Trifluoromethylated analogs of macrosphelide A I and 2 were designed and synthesized. The key segment 6 was efficiently constructed via a series of high stereoselective transformations from trifluoromethylated diol 8. Methoxymethylation of compound 9 with 14 1.0 equiv of sodium hydride gave optically pure compound 23a in 73% yield. From 23a a novel route was developed to prepare key segment 7. The condensation and macrolactonization were smoothly proceeded under our modified Keck's protocol. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.10.019
• 作为产物：
  描述：

  、 Triphenyl<(2,2,2-trichlorethoxycarbonyl)methylen>phosphoran 以 二氯甲烷 为溶剂， 以2.12 g的产率得到(4R,5R,E)-2,2,2-trichloroethyl 4-(benzyloxy)-6,6,6-trifluoro-5-(methoxymethylenoxy)hex-2-enoate
  参考文献：
  名称：

  Total synthesis of trifluoromethylated analogs of macrosphelide A

  摘要：

  Trifluoromethylated analogs of macrosphelide A I and 2 were designed and synthesized. The key segment 6 was efficiently constructed via a series of high stereoselective transformations from trifluoromethylated diol 8. Methoxymethylation of compound 9 with 14 1.0 equiv of sodium hydride gave optically pure compound 23a in 73% yield. From 23a a novel route was developed to prepare key segment 7. The condensation and macrolactonization were smoothly proceeded under our modified Keck's protocol. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.10.019

文献信息

• Total synthesis of trifluoromethylated analogs of macrosphelide A
  作者：Bing-Lin Wang、Zhong-Xing Jiang、Zheng-Wei You、Feng-Ling Qing

  DOI：10.1016/j.tet.2007.10.019

  日期：2007.12

  Trifluoromethylated analogs of macrosphelide A I and 2 were designed and synthesized. The key segment 6 was efficiently constructed via a series of high stereoselective transformations from trifluoromethylated diol 8. Methoxymethylation of compound 9 with 14 1.0 equiv of sodium hydride gave optically pure compound 23a in 73% yield. From 23a a novel route was developed to prepare key segment 7. The condensation and macrolactonization were smoothly proceeded under our modified Keck's protocol. (c) 2007 Elsevier Ltd. All rights reserved.