(4E)-1,1-bis(methoxymethyl)-3-((Z)-penta-2,4-dienyl)-4-propylidenecyclopentane

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4E)-1,1-bis(methoxymethyl)-3-((Z)-penta-2,4-dienyl)-4-propylidenecyclopentane
• 英文别名: (4E)-1,1-bis(methoxymethyl)-3-[(2Z)-penta-2,4-dienyl]-4-propylidenecyclopentane
• 化学式: C₁₇H₂₈O₂
• 分子量: 264.408
• InChiKey: UHBINXABEXXSFA-USTJKHOZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  19
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  顺式-1,4-二氯-2-丁烯 、 4,4-bis(methoxymethyl)non-1-en-6-yne 在 正丁基锂 、 二氯二茂锆 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 0.5h， 以81%的产率得到(4E)-1,1-bis(methoxymethyl)-3-((Z)-penta-2,4-dienyl)-4-propylidenecyclopentane
  参考文献：
  名称：

  Ring expansion of 5- to 6-member zirconacycles by carbenoid insertion

  摘要：

  A wide range of carbenoids (1-lithio-1-halo species), including those with alpha-SiR3, OEt, SPh, SO2Ph, P(O)(OEt)(2), and CN substituents, insert into 5-member zirconacycles (saturated and unsaturated, mono- and bi-cyclic) to afford functionalized 6-member zirconacycles. 1-Lithio-1-haloalkenes insert to afford 6-member zirconacycles with an alkylidene substituent next to the metal. Unexpected double insertion of some carbenoids, and evidence for endocylic beta-hydride transfer processes provide additional mechanistic interest. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2003.09.056

文献信息

• Ring expansion of 5- to 6-member zirconacycles by carbenoid insertion
  作者：Sally Dixon、Shaun M. Fillery、Aleksandra Kasatkin、David Norton、Emma Thomas、Richard J. Whitby

  DOI：10.1016/j.tet.2003.09.056

  日期：2004.2

  A wide range of carbenoids (1-lithio-1-halo species), including those with alpha-SiR3, OEt, SPh, SO2Ph, P(O)(OEt)(2), and CN substituents, insert into 5-member zirconacycles (saturated and unsaturated, mono- and bi-cyclic) to afford functionalized 6-member zirconacycles. 1-Lithio-1-haloalkenes insert to afford 6-member zirconacycles with an alkylidene substituent next to the metal. Unexpected double insertion of some carbenoids, and evidence for endocylic beta-hydride transfer processes provide additional mechanistic interest. (C) 2003 Elsevier Ltd. All rights reserved.