2-(2-ethyl-1,3-dioxolan-2-yl)-2-methylpropanal | 311761-29-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(2-ethyl-1,3-dioxolan-2-yl)-2-methylpropanal
• CAS: 311761-29-2
• 化学式: C₉H₁₆O₃
• 分子量: 172.224
• InChiKey: QTZVMDIMLVLVNG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(2-ethyl-1,3-dioxolan-2-yl)-2-methylpropanal 在 咪唑 、 4-二甲氨基吡啶 、 双(乙腈)氯化钯(II) 、 锂硼氢 、 N,N-二异丙基乙胺 、 9-硼杂双环[3.3.1]壬基三氟甲磺酸酯 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 8.25h， 生成 2-[(4S)-2,2-dimethyl-1,3-dioxan-4-yl]-2-methyl-3-pentanon
  参考文献：
  名称：

  An Unusual Reversal of Stereoselectivity in a Boron Mediated Aldol Reaction: Enantioselective Synthesis of the C1–C6 Segment of the Epothilones

  摘要：

  Enantioselective syntheses of differentially protected C-1-C-6 fragments, (3S)-3-hydroxy-4,4-dimethyl-5-oxoheptanoic acid 4, (5S)-7-[1,1-bis(mechylethyl)-2-methyl-1 -silapropoxy]-5-hydroxy-4,4-dimethylheptan-3-one 5 and (4S)-2-(2,2-dimethyl-1,3-dioxan-4-yl)-2-methylpentan-3-one 23, common to both epothilones A and B, are reported. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00708-0
• 作为产物：
  描述：

  3,3-dimethyl-4-oxohex-1-ene 在 4-甲基苯磺酸吡啶 、 臭氧 作用下， 以 甲醇 、 苯 为溶剂， 反应 33.0h， 生成 2-(2-ethyl-1,3-dioxolan-2-yl)-2-methylpropanal
  参考文献：
  名称：

  An Unusual Reversal of Stereoselectivity in a Boron Mediated Aldol Reaction: Enantioselective Synthesis of the C1–C6 Segment of the Epothilones

  摘要：

  Enantioselective syntheses of differentially protected C-1-C-6 fragments, (3S)-3-hydroxy-4,4-dimethyl-5-oxoheptanoic acid 4, (5S)-7-[1,1-bis(mechylethyl)-2-methyl-1 -silapropoxy]-5-hydroxy-4,4-dimethylheptan-3-one 5 and (4S)-2-(2,2-dimethyl-1,3-dioxan-4-yl)-2-methylpentan-3-one 23, common to both epothilones A and B, are reported. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00708-0

文献信息

• Rhenium(I)-Catalyzed Cyclization of Silyl Enol Ethers Containing a Propargyl Carboxylate Moiety: Versatile Access to Highly Substituted Phenols
  作者：Kodai Saito、Yuji Onizawa、Hiroyuki Kusama、Nobuharu Iwasawa

  DOI：10.1002/chem.200903586

  日期：2010.4.26

  containing an acyloxy substituent at the propargylic position gave highly substituted phenols in good yields (see scheme). Depending on the structure of the silyl enol ether, either nucleophilic addition of this moiety or 1,2‐acyloxy migration occurs to give two kinds of synthetically useful, substituted phenols.

  选择性迁移：在炔丙基位置含有酰氧基取代基的2-甲氧基-1-en-5-炔烃的rh催化反应可得到高取代度的苯酚，收率很高（参见方案）。取决于甲硅烷基烯醇醚的结构，该部分的亲核加成或1,2-酰氧基的迁移都会产生两种合成上有用的取代酚。
• An Unusual Reversal of Stereoselectivity in a Boron Mediated Aldol Reaction: Enantioselective Synthesis of the C1–C6 Segment of the Epothilones
  作者：Bijoy Panicker、Jean M Karle、Mitchell A Avery

  DOI：10.1016/s0040-4020(00)00708-0

  日期：2000.9

  Enantioselective syntheses of differentially protected C-1-C-6 fragments, (3S)-3-hydroxy-4,4-dimethyl-5-oxoheptanoic acid 4, (5S)-7-[1,1-bis(mechylethyl)-2-methyl-1 -silapropoxy]-5-hydroxy-4,4-dimethylheptan-3-one 5 and (4S)-2-(2,2-dimethyl-1,3-dioxan-4-yl)-2-methylpentan-3-one 23, common to both epothilones A and B, are reported. (C) 2000 Elsevier Science Ltd. All rights reserved.