2,2,2-trichloroethyl (Z)-3-ethoxy-2-(2-oxaspiro[4.5]dec-3-ylidene)butanoate | 1005737-76-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃类
• 英文名称: 2,2,2-trichloroethyl (Z)-3-ethoxy-2-(2-oxaspiro[4.5]dec-3-ylidene)butanoate
• 英文别名: 2,2,2-trichloroethyl (2Z)-3-ethoxy-2-(2-oxaspiro[4.5]dec-3-ylidene)butanoate；2,2,2-trichloroethyl (2Z)-3-ethoxy-2-(2-oxaspiro[4.5]decan-3-ylidene)butanoate
• CAS: 1005737-76-7
• 化学式: C₁₇H₂₅Cl₃O₄
• 分子量: 399.742
• InChiKey: ZUSUYUATHQHXKM-YPKPFQOOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,2,2-trichloroethyl (Z)-3-ethoxy-2-(2-oxaspiro[4.5]dec-3-ylidene)butanoate 在 1,5-已二烯 、 platinum(II) chloride 作用下， 以 甲苯 为溶剂， 反应 4.0h， 生成 2,2,2-trichloroethyl (E)-3-ethoxy-2-(2-oxaspiro[4.5]dec-3-ylidene)butanoate
  参考文献：
  名称：

  酯基或烯烃配体在铂催化6-（1-烷氧基乙氧基）-己-2-炔酸酯的羰基烷氧基化反应中的立体化学控制

  摘要：

  Abstractmagnified imageThe cyclization of 6‐(1‐alkoxyethoxy)hex‐2‐ynoantes in the presence of the platinum‐olefin catalyst system gave the corresponding multisubstituted 2‐[dihydrofuran‐2(3H)‐ylidene]acetates in good to high yields. The Z/E selectivity is controlled by the electronic property of the ester group; the 2,2,2‐trichloroethyl ester yielded the Z isomer, while the phenyl ester gave the E isomer. Moreover, we found that the Z/E selectivities in the reaction of phenyl esters 1h, 1n, and 1o were controlled by the olefin ligand. For example, the platinum‐catalyzed reaction of 1h using 1,5‐hexadiene as the olefin ligand gave E‐2h as the major product, while that using 1,5‐cyclooctadiene produced mainly the Z isomer.

  DOI：

  10.1002/adsc.200800772
• 作为产物：
  描述：

  2,2,2-Trichloroethyl 4-[1-(1-ethoxyethoxymethyl)cyclohexyl]but-2-ynoate 在 1,5-已二烯 、 platinum(II) chloride 作用下， 以 甲苯 为溶剂， 反应 4.0h， 生成 2,2,2-trichloroethyl (E)-3-ethoxy-2-(2-oxaspiro[4.5]dec-3-ylidene)butanoate 、 2,2,2-trichloroethyl (Z)-3-ethoxy-2-(2-oxaspiro[4.5]dec-3-ylidene)butanoate
  参考文献：
  名称：

  酯基或烯烃配体在铂催化6-（1-烷氧基乙氧基）-己-2-炔酸酯的羰基烷氧基化反应中的立体化学控制

  摘要：

  Abstractmagnified imageThe cyclization of 6‐(1‐alkoxyethoxy)hex‐2‐ynoantes in the presence of the platinum‐olefin catalyst system gave the corresponding multisubstituted 2‐[dihydrofuran‐2(3H)‐ylidene]acetates in good to high yields. The Z/E selectivity is controlled by the electronic property of the ester group; the 2,2,2‐trichloroethyl ester yielded the Z isomer, while the phenyl ester gave the E isomer. Moreover, we found that the Z/E selectivities in the reaction of phenyl esters 1h, 1n, and 1o were controlled by the olefin ligand. For example, the platinum‐catalyzed reaction of 1h using 1,5‐hexadiene as the olefin ligand gave E‐2h as the major product, while that using 1,5‐cyclooctadiene produced mainly the Z isomer.

  DOI：

  10.1002/adsc.200800772

文献信息

• Synthesis of Multisubstituted 2-(Dihydrofuran-2(3H)-ylidene)acetates via Intramolecular Carboalkoxylation by Platinum−Olefin Catalyst System
  作者：Itaru Nakamura、Ching Siew Chan、Toshiharu Araki、Masahiro Terada、Yoshinori Yamamoto

  DOI：10.1021/ol702795u

  日期：2008.1.1

  The cyclization of 6-(1-alkoxyethyl)hex-2-ynoates in the presence of a platinum-olefin catalyst system gave the corresponding multisubstituted 2-(dihydrofuran-2(3H)-ylidene)acetates in good to high yields. The Z/E selectivity is controlled by the electronic property of the ester group; the 2,2,2-trichloroethyl ester led to the Z isomer, while the phenyl ester gave the E isomer.