2-(Chloromethyl)-3-(methoxymethoxy)prop-1-ene | 1353653-55-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(Chloromethyl)-3-(methoxymethoxy)prop-1-ene
• CAS: 1353653-55-0
• 化学式: C₆H₁₁ClO₂
• 分子量: 150.605
• InChiKey: YSBNQSWREOMBSN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  9
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(Chloromethyl)-3-(methoxymethoxy)prop-1-ene 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 potassium hydride 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 2.33h， 生成 C₂₈H₄₄O₆
  参考文献：
  名称：

  Ring-closing metathesis and palladium-catalyzed formate reduction to 3-methyleneoxepanes. Formal synthesis of (−)-zoapatanol

  摘要：

  A sequence of ring-closing metathesis and palladium-catalyzed formate reduction was developed for preparing O-heterocycles with an exocyclic olefin and applied to the asymmetric synthesis of zoapatanol. The key vicinal stereocenters in zoapatanol were constructed from the L-malic acid-derived lactone by successive chelation-controlled addition of alkyl groups. The O-allylations to prepare the dienes for RCM were achieved with the tertiary alcohols bearing internal olefins. The ring opening of oxepane, a new reaction pathway for the Pd-formate reduction, is also reported. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.10.023
• 作为产物：
  描述：

  氯甲基甲基醚 、 3-chloro-2-(hydroxymethyl)-1-propene 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 以80%的产率得到2-(Chloromethyl)-3-(methoxymethoxy)prop-1-ene
  参考文献：
  名称：

  Ring-closing metathesis and palladium-catalyzed formate reduction to 3-methyleneoxepanes. Formal synthesis of (−)-zoapatanol

  摘要：

  A sequence of ring-closing metathesis and palladium-catalyzed formate reduction was developed for preparing O-heterocycles with an exocyclic olefin and applied to the asymmetric synthesis of zoapatanol. The key vicinal stereocenters in zoapatanol were constructed from the L-malic acid-derived lactone by successive chelation-controlled addition of alkyl groups. The O-allylations to prepare the dienes for RCM were achieved with the tertiary alcohols bearing internal olefins. The ring opening of oxepane, a new reaction pathway for the Pd-formate reduction, is also reported. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.10.023

文献信息

• Ring-closing metathesis and palladium-catalyzed formate reduction to 3-methyleneoxepanes. Formal synthesis of (−)-zoapatanol
  作者：Hsiu-Yi Cheng、Yu-Shiang Lin、Chong-Si Sun、Ting-Wen Shih、Hui-Hsu Gavin Tsai、Duen-Ren Hou

  DOI：10.1016/j.tet.2011.10.023

  日期：2012.1

  A sequence of ring-closing metathesis and palladium-catalyzed formate reduction was developed for preparing O-heterocycles with an exocyclic olefin and applied to the asymmetric synthesis of zoapatanol. The key vicinal stereocenters in zoapatanol were constructed from the L-malic acid-derived lactone by successive chelation-controlled addition of alkyl groups. The O-allylations to prepare the dienes for RCM were achieved with the tertiary alcohols bearing internal olefins. The ring opening of oxepane, a new reaction pathway for the Pd-formate reduction, is also reported. (C) 2011 Elsevier Ltd. All rights reserved.