(2E)-1,4-diphenyl-2-butene-1,4-diol | 2085-99-6

• 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: (2E)-1,4-diphenyl-2-butene-1,4-diol
• 英文别名: (E)-1,4-diphenylbut-2-ene-1,4-diol；trans-1,4-Diphenyl-2-buten-1,4-diol；1,4-Diphenyl-2-buten-1,4-diol；2-Butene, 1,4-diol-1,4-diphenyl
• CAS: 2085-99-6
• 化学式: C₁₆H₁₆O₂
• 分子量: 240.302
• InChiKey: RXFAALFDAWXYOP-VAWYXSNFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2E)-1,4-diphenyl-2-butene-1,4-diol 在 咪唑 、 甲醇银 、 m-carbaboranylmercuric chloride 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 28.0h， 生成 1,4-二苯基-1,3丁二烯
  参考文献：
  名称：

  用于还原脱氧的 m-C2B10H11HgCl/AgOTf 催化反应

  摘要：

  已开发出 m -C 2 B 10 H 11 HgCl/AgOTf 催化的烯丙基甲硅烷基醚与 N -Boc-N '-甲苯磺酰肼的反应。在温和的条件下，所得的烯丙基肼产物以良好的收率转化为裸烯烃。此外，使用过的m -C 2 B 10 H 11 HgCl 可以定量回收。

  DOI：

  10.1055/s-0036-1588554
• 作为产物：
  描述：

  苯甲醛 在 lithium aluminium tetrahydride 、 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 生成 (2E)-1,4-diphenyl-2-butene-1,4-diol
  参考文献：
  名称：

  Unsaturated syn- and anti-1,2-Amino Alcohols by Cyclization of Allylic Bis-trichloroacetimidates. Stereoselectivity Dependence on Substrate Configuration

  摘要：

  Disubstituted allylic bis-imidates undergo Lewis acid catalyzed or spontaneous cyclization to oxazolines, which are precursors of unsaturated amino alcohols. Stereoselectivity of the cyclization is mainly determined by the substrate configuration. Highly selective cis-oxazoline formation is achieved starting from anti-E-bis-imidates while trans-oxazoline predominantly forms from anti-Z-bis-imidates. On the basis of DFT calculations, the stereoselectivity trends can be explained by the formation of the energetically most stable carbenium ion conformation, followed by the cyclization via most favorable bond rotations.

  DOI：

  10.1021/jo502404y

文献信息

• INAMURA, YASA;INAMURA, YUTAKA, J. CHEM. SOC. JAP., CHEM. AND IND. CHEM., 1985, N 1, 134-137
  作者：INAMURA, YASA、INAMURA, YUTAKA

  DOI：——

  日期：——
• US3975381A
  申请人：——

  公开号：US3975381A

  公开（公告）日：1976-08-17
• US5151333A
  申请人：——

  公开号：US5151333A

  公开（公告）日：1992-09-29
• m-C2B10H11HgCl/AgOTf-Catalyzed Reaction for Reductive Deoxygenation
  作者：Naoto Yamasaki、Marina Kanno、Kyohei Sakamoto、Yusuke Kasai、Hiroshi Imagawa、Hirofumi Yamamoto

  DOI：10.1055/s-0036-1588554

  日期：2018.1

  A m -C 2 B 10 H 11 HgCl/AgOTf-catalyzed reaction of allyl silyl ethers with N -Boc- N ′-tosylhydrazine has been developed. Under mild conditions, the resulting allyl hydrazine products were transformed into naked alkenes in good yield. Furthermore, the used m -C 2 B 10 H 11 HgCl could be recovered quantitatively.

  已开发出 m -C 2 B 10 H 11 HgCl/AgOTf 催化的烯丙基甲硅烷基醚与 N -Boc-N '-甲苯磺酰肼的反应。在温和的条件下，所得的烯丙基肼产物以良好的收率转化为裸烯烃。此外，使用过的m -C 2 B 10 H 11 HgCl 可以定量回收。
• Unsaturated <i>syn</i>- and <i>anti</i>-1,2-Amino Alcohols by Cyclization of Allylic Bis-trichloroacetimidates. Stereoselectivity Dependence on Substrate Configuration
  作者：Liene Grigorjeva、Artis Kinens、Aigars Jirgensons

  DOI：10.1021/jo502404y

  日期：2015.1.16

  Disubstituted allylic bis-imidates undergo Lewis acid catalyzed or spontaneous cyclization to oxazolines, which are precursors of unsaturated amino alcohols. Stereoselectivity of the cyclization is mainly determined by the substrate configuration. Highly selective cis-oxazoline formation is achieved starting from anti-E-bis-imidates while trans-oxazoline predominantly forms from anti-Z-bis-imidates. On the basis of DFT calculations, the stereoselectivity trends can be explained by the formation of the energetically most stable carbenium ion conformation, followed by the cyclization via most favorable bond rotations.