4-ethoxycarbonyl-2'-propenyl-2,4'-bithiazole | 881012-96-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-ethoxycarbonyl-2'-propenyl-2,4'-bithiazole
• 英文别名: Ethyl 2-(2-prop-1-en-2-yl-1,3-thiazol-4-yl)-1,3-thiazole-4-carboxylate
• CAS: 881012-96-0
• 化学式: C₁₂H₁₂N₂O₂S₂
• 分子量: 280.371
• InChiKey: JYQIZEJRTORRRP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  109
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-ethoxycarbonyl-2'-propenyl-2,4'-bithiazole 在 lipase Godo E-1 sodium hydroxide 、 硼烷四氢呋喃络合物 、 双氧水 作用下， 以 四氢呋喃 、 吡啶 、 异丙醚 、 水 为溶剂， 反应 43.25h， 生成 (S)-4-ethoxycarbonyl-2'-(1-hydroxymethylethyl)-2,4'-bithiazole
  参考文献：
  名称：

  Total synthesis of (4R,5S,6E,14S)- and (4R,5S,6E,14R)-cystothiazoles F

  摘要：

  Total synthesis of (4R,5S,6E,14S)- and (4R,5S,6E,14R)-cystothiazoles F 3 was achieved from the chiral bithiazole-type primary alcohols [(S)- and (R)-4-ethoxycarbonyl-2'-(1-hydroxymethylethyl)-2,4'-bithiazoles 8], which were obtained based on the enzymatic resolution of racemic alcohol 8 and its acetate 9. From a direct comparison by means of chiral HPLC between natural cystothiazole F 3 and synthetic compounds [(4R,5S,6E,14S)- and (4R,5S,6E,14R)-cystothiazoles 3], natural cystothiazole F 3 was found to be a 33:67 diastereomeric mixture [(4R,5S,6E,14S)-3:(4R,5S,6E,14R)-3 = 33:67]. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2007.02.011
• 作为产物：
  描述：

  2'-[2''-hydroxyisopropyl(2,4')bithiazolyl]-4-carboxylic acid ethyl ester 在 对甲苯磺酸 作用下， 以 苯 为溶剂， 反应 2.0h， 以88%的产率得到4-ethoxycarbonyl-2'-propenyl-2,4'-bithiazole
  参考文献：
  名称：

  (4R,5S)-甲基噻唑 B 和 M 的合成

  摘要：

  报道的 (+)-手性醛 [(4R,5R)-5] 与衍生自联噻唑型碘化鏻 (6) 的磷酰苯胺之间的 Wittig 反应，使用双(三甲基甲硅烷基)氨基锂得到 (+)-甲基噻唑 B (1)，其光谱数据与来自粘细菌 Archangium gephyra 菌株 Ar 7747 的天然 (+)-1 的光谱数据相同。此外，(+)-(4R,5R)-5 和联噻唑之间的选择性烯烃形成- 型砜 [(')-7] 然后转化得到 (+)-甲基噻唑 M (2)，其光谱数据与来自粘杆菌 Archangium gephyra 菌株 Ar 7747 的天然 (+)-2 的光谱数据相同。

  DOI：

  10.3987/com-05-s(k)8

文献信息

• Asymmetric syntheses and structure elucidation of cystothiazole A metabolites of the myxobacterium Cystobacter fuscus
  作者：Yuki Iwaki、Shigeo Yamamura、Hiroyuki Akita

  DOI：10.1016/j.tetasy.2008.08.029

  日期：2008.9

  Convergent syntheses of (14R,15)- and (14S,15)-dihydroxycystothiazole A 4 were achieved based on a Julia-Kocienski coupling between the functionalized aldehyde (2E)-6 or (2Z)-6, corresponding to the left-side, and chiral sulfones (14R)-16 and (14S)-16, bearing a bithiazole moiety corresponding to the right-side, respectively. The absolute configuration of natural (14,15)-dihydroxycystothiazoles A 4 was determined to be (4R,5S,14S) by comparison of the physical data, including the sign of specific rotation, between synthetic (2E,4R,5S,6E,14S)-4 and natural 4. Deprotections of the silyl group and cyclopentane moiety of the coupled product (2E,4R,5S,6E,14R)-17 gave (14R,15)-dihydroxycystothiazole C 5, which was consistent with natural 5 corresponding to the minor isomer, including the sign of specific rotation. Likewise, deprotection of the silyl group and cyclopentane moiety of the coupled product (2E,4R,5S,6E,14S)-17 afforded (14S,15)-dihydroxycystothiazole C 5, which was consistent with natural 5 corresponding to the major isomer, including the sign of specific rotation. Finally, convergent synthesis of 14-hydroxycystothiazole C 3 was achieved based on the modified (one-pot) Julia olefination between the aldehyde (2Z)-6 and bithiazole sulfone 22. The absolute configurations of natural 14-hydroxycystothiazole C 3 were confirmed to be (4R) and (5S). Methylation of synthetic 3 gave cystothiazole B 2. (C) 2008 Elsevier Ltd. All rights reserved.