(E)-((octa-5,7-dien-1-yloxy)methyl)benzene | 865191-40-8

• 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: (E)-((octa-5,7-dien-1-yloxy)methyl)benzene
• 英文别名: [(5E)-octa-5,7-dienoxy]methylbenzene
• CAS: 865191-40-8
• 化学式: C₁₅H₂₀O
• 分子量: 216.323
• InChiKey: YGCFFENPKBNUAY-ONEGZZNKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  16
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (E)-((octa-5,7-dien-1-yloxy)methyl)benzene 在 AD-mix-β 作用下， 生成 (E)-8-Benzyloxy-oct-3-ene-1,2-diol 、 (3S,4S)-8-Benzyloxy-oct-1-ene-3,4-diol
  参考文献：
  名称：

  Palladium-catalyzed and organozinc-promoted synthesis of dienes from allylic esters possessing an acyloxy or alkoxy group

  摘要：

  Organozinc and a Pd catalyst promoted formation of dienes from allylic esters possessing a leaving group such as acyloxy and alkoxy groups next to the allyl moiety. The reaction proceeded with high regio- and stereoselectivity when applied to secondary allylic substrates. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.06.146
• 作为产物：
  描述：

  (E)-8-Benzyloxy-oct-3-ene-1,2-diol 在 四(三苯基膦)钯 、 正丁基氯化镁 、 zinc(II) chloride 作用下， 以 四氢呋喃 为溶剂， 反应 0.33h， 生成 (E)-((octa-5,7-dien-1-yloxy)methyl)benzene
  参考文献：
  名称：

  Palladium-catalyzed and organozinc-promoted synthesis of dienes from allylic esters possessing an acyloxy or alkoxy group

  摘要：

  Organozinc and a Pd catalyst promoted formation of dienes from allylic esters possessing a leaving group such as acyloxy and alkoxy groups next to the allyl moiety. The reaction proceeded with high regio- and stereoselectivity when applied to secondary allylic substrates. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.06.146

文献信息

• Ligand effects on the stereochemistry of Stille couplings, as manifested in reactions of Z-alkenyl halides
  作者：Guo-ping Lu、Karl R. Voigtritter、Chun Cai、Bruce H. Lipshutz

  DOI：10.1039/c2cc33294a

  日期：——

  Unexpected losses in stereochemistry from Stille reactions involving Z-alkenyl halides have been shown to be ligand dependent. A new set of reaction conditions has been developed that, in most cases, leads to highly stereoselective cross-couplings under mild conditions, along with improved yields.

  涉及Z-烯基卤化物的Stille反应的立体化学意外损失已显示是配体依赖性的。已开发出一套新的反应条件，在大多数情况下，它们会在温和条件下导致高度立体选择性的交叉偶联，并提高产率。
• US4078005A
  申请人：——

  公开号：US4078005A

  公开（公告）日：1978-03-07
• Palladium-catalyzed and organozinc-promoted synthesis of dienes from allylic esters possessing an acyloxy or alkoxy group
  作者：Hatsuhiko Hattori、Masahiro Katsukawa、Yuichi Kobayashi

  DOI：10.1016/j.tetlet.2005.06.146

  日期：2005.8

  Organozinc and a Pd catalyst promoted formation of dienes from allylic esters possessing a leaving group such as acyloxy and alkoxy groups next to the allyl moiety. The reaction proceeded with high regio- and stereoselectivity when applied to secondary allylic substrates. (c) 2005 Elsevier Ltd. All rights reserved.