(3R,4R)-4-hydroxyhexa-1,5-dien-3-yl acetate | 144118-28-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (3R,4R)-4-hydroxyhexa-1,5-dien-3-yl acetate
• CAS: 144118-28-5
• 化学式: C₈H₁₂O₃
• 分子量: 156.181
• InChiKey: KNJNUBWIEQLTOD-HTQZYQBOSA-N

反应信息

• 作为反应物：
  描述：

  (3R,4R)-4-hydroxyhexa-1,5-dien-3-yl acetate 、 3-溴丙炔 在 sodium hydride 作用下， 以 四氢呋喃 、 mineral oil 为溶剂， 反应 12.5h， 以43%的产率得到(3R,4R)-4-(prop-2-ynyloxy)hexa-1,5-dien-3-yl acetate
  参考文献：
  名称：

  Ring-Size-Selective Enyne Metathesis as a Tool for Desymmetrization of an EnantiopureC₂-Symmetric Building Block

  摘要：

  The enantiomerically pure C-2-syrnmetrical hexa-1,5-diene-3,4-diol is selectively monopropargylated. The products undergo ring-closing enyne metathesis to give exclusively dihydropyrans as single stereoisomers. An unprotected hydroxy group is identified as the factor controlling the ring-size selectivity.

  DOI：

  10.1021/jo9018649
• 作为产物：
  描述：

  (3R,4R)-1,5-hexadiene-3,4-diol 、 乙酸酐 在 cerium(III) chloride heptahydrate 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 以98%的产率得到(3R,4R)-4-hydroxyhexa-1,5-dien-3-yl acetate
  参考文献：
  名称：

  Ring-Size-Selective Enyne Metathesis as a Tool for Desymmetrization of an EnantiopureC₂-Symmetric Building Block

  摘要：

  The enantiomerically pure C-2-syrnmetrical hexa-1,5-diene-3,4-diol is selectively monopropargylated. The products undergo ring-closing enyne metathesis to give exclusively dihydropyrans as single stereoisomers. An unprotected hydroxy group is identified as the factor controlling the ring-size selectivity.

  DOI：

  10.1021/jo9018649

文献信息

• Total Synthesis of (−)-Cleistenolide
  作者：Bernd Schmidt、Oliver Kunz、Anne Biernat

  DOI：10.1021/jo1002642

  日期：2010.4.2

  The first total synthesis of Cleistenolide, a novel natural product recently isolated from the Annonaceae species Cleistochlamys kirkii Oliver, is described. The synthesis proceeds in six steps and 18% overall yield, starting from an enantiopure C2-symmetric building block and using a Sharpless epoxidation, a selective epoxide opening, and a ring-closing metathesis reaction.

  描述了油香烯内酯的首次全合成，油香烯内酯是最近从番荔枝科植物油茶（Cleistochlamys kirkii Oliver）中分离出来的一种新型天然产物。从对映体纯的C2对称结构单元开始，并使用Sharpless环氧化，选择性环氧化物开环和闭环易位反应，合成过程以六个步骤和18％的总收率进行。