ethyl (2E,4S)-4,5-diacetoxy-2-pentenoate | 150501-81-8

• 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: ethyl (2E,4S)-4,5-diacetoxy-2-pentenoate
• 英文别名: ethyl (E,4S)-4,5-diacetyloxypent-2-enoate
• CAS: 150501-81-8
• 化学式: C₁₁H₁₆O₆
• 分子量: 244.244
• InChiKey: XIDHTPVJFAOUEZ-PORFMDCZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  17
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  78.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  ethyl (2E,4S)-4,5-diacetoxy-2-pentenoate 在 盐酸羟胺 、 sodium acetate 、 叔丁醇 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 乙醇 、 正己烷 为溶剂， 反应 5.0h， 生成 ethyl (2R,3R)-3-<(S)-1,2-diacetoxyethyl>-5-oxopyrrolidine-2-carboxylate
  参考文献：
  名称：

  Double chiral induction in ul-selective Michael additions of metal enolates of N-bornylideneglycinates to (E)-4,5-dioxy-2-pentenoates. Exclusive ul,lk-1,2-chiral induction leading to l,u-Michael adducts

  摘要：

  ul-Selective Michael additions of metal enolates of ethyl N-[(1R,4R)-bornylidene]glycinate to optically pure (E)-4,5-dioxy-2-pentenoates, such as ethyl (E)-3-(2,2-dimethyl-1,3-dioxolan-4-yl)propenoate, ethyl (E)-3-(1,3-dioxolan-4-yl)propenoate, and ethyl (E)-4,5-diacetoxy-2-pentenoate, proceed through ul,lk-1,2-induction to provide pure enantiomers of 4-substituted 2-oxopyrrolidine-5-carboxylates as single diastereomers. Exclusive ul,lk-1,2-induction is achieved by use of the racemic enolates. Origin of such high stereocontrol is discussed by Kozikowski's antiperiplanar transition model.

  DOI：

  10.1021/jo00068a016
• 作为产物：
  描述：

  ethyl (2'S)-3-(1',4'-dioxa-spiro[4.5]dec-2'-yl)-acrylate 在 吡啶 、 盐酸 、 4-二甲氨基吡啶 作用下， 以 四氢呋喃 为溶剂， 生成 ethyl (2E,4S)-4,5-diacetoxy-2-pentenoate
  参考文献：
  名称：

  手性烯烃的不对称二羟基化。高度控制非对颌面选择

  摘要：

  描述了使用手性N，N′-二烷基-2，2′-联吡咯烷配体（1）用四氧化对4，5-二羟基-2-戊烯酸酯的高度非对映选择性二羟基化。通过使用对映异构体配体，可以对乙酸盐（2d）和甲基醚（2e）进行顺式或反式选择。

  DOI：

  10.1016/s0040-4039(00)73639-2

文献信息

• Double chiral induction in ul-selective Michael additions of metal enolates of N-bornylideneglycinates to (E)-4,5-dioxy-2-pentenoates. Exclusive ul,lk-1,2-chiral induction leading to l,u-Michael adducts
  作者：Akira Tatsukawa、Masashi Dan、Mika Ohbatake、Keiko Kawatake、Tomohiro Fukata、Eiji Wada、Shuji Kanemasa、Shoichi Kakei

  DOI：10.1021/jo00068a016

  日期：1993.7

  ul-Selective Michael additions of metal enolates of ethyl N-[(1R,4R)-bornylidene]glycinate to optically pure (E)-4,5-dioxy-2-pentenoates, such as ethyl (E)-3-(2,2-dimethyl-1,3-dioxolan-4-yl)propenoate, ethyl (E)-3-(1,3-dioxolan-4-yl)propenoate, and ethyl (E)-4,5-diacetoxy-2-pentenoate, proceed through ul,lk-1,2-induction to provide pure enantiomers of 4-substituted 2-oxopyrrolidine-5-carboxylates as single diastereomers. Exclusive ul,lk-1,2-induction is achieved by use of the racemic enolates. Origin of such high stereocontrol is discussed by Kozikowski's antiperiplanar transition model.
• Asymmetric dihydroxylation of chiral olefins. High control of diastereofacial selection
  作者：Tohru Oishi、Kyo-ichiro Iida、Masahiro Hirama

  DOI：10.1016/s0040-4039(00)73639-2

  日期：1993.5

  Highly diastereoselective dihydroxylation of 4,5-dihydroxy-2-pentenoate with osmium tetroxide using chiral N,N'-dialkyl-2,2′-bipyrrolidine ligands (1) is described. Either syn or anti selection was achieved for acetate (2d) and methyl ether (2e) by employing the enantiomeric ligands.

  描述了使用手性N，N′-二烷基-2，2′-联吡咯烷配体（1）用四氧化对4，5-二羟基-2-戊烯酸酯的高度非对映选择性二羟基化。通过使用对映异构体配体，可以对乙酸盐（2d）和甲基醚（2e）进行顺式或反式选择。