2-((4R)-2,2-dimethyl-[1,3]dioxolan-4-ylmethylene)-malonic acid dimethyl ester | 204390-79-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 2-((4R)-2,2-dimethyl-[1,3]dioxolan-4-ylmethylene)-malonic acid dimethyl ester
• 英文别名: dimethyl 2-[[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]methylidene]propanedioate
• CAS: 204390-79-4
• 化学式: C₁₁H₁₆O₆
• 分子量: 244.244
• InChiKey: IUMZIORBHMYPIM-SSDOTTSWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-((4R)-2,2-dimethyl-[1,3]dioxolan-4-ylmethylene)-malonic acid dimethyl ester 在 锂硼氢 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 7.5h， 生成 (3R,3AS,6AR)-六氢呋喃并[2,3-B]呋喃-3-醇
  参考文献：
  名称：

  Stereoselective and Efficient Synthesis of (3R,3aS,6aR)-Hexahydrofuro[2,3-b]furan-3-ol

  摘要：

  [GRAPHICS]Two short and efficient synthesis routes have been developed for bis-THF-alcohol 2, a key building block of the investigational HIV protease inhibitor TMC114 (1). Using S-2,3-O-isopropylideneglyceraldehyde (4) as the source of chirality, both routes are based on a diastereoselective Michael addition of nitromethane to give predominantly the syn congeners 6 followed by a Nef oxidation and cyclization to afford lactone acetals 8, which are reduced and cyclized to give 2.

  DOI：

  10.1021/ol052554i
• 作为产物：
  描述：

  (3S,4R,5S)-5-[(4S)-2,2-二甲基-1,3-二氧戊环-4-基]-3,4-二羟基二氢-2(3H)-呋喃酮 在 吡啶 、 potassium metaperiodate 、 乙酸酐 、 potassium hydrogencarbonate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 16.5h， 生成 2-((4R)-2,2-dimethyl-[1,3]dioxolan-4-ylmethylene)-malonic acid dimethyl ester
  参考文献：
  名称：

  Stereoselective and Efficient Synthesis of (3R,3aS,6aR)-Hexahydrofuro[2,3-b]furan-3-ol

  摘要：

  [GRAPHICS]Two short and efficient synthesis routes have been developed for bis-THF-alcohol 2, a key building block of the investigational HIV protease inhibitor TMC114 (1). Using S-2,3-O-isopropylideneglyceraldehyde (4) as the source of chirality, both routes are based on a diastereoselective Michael addition of nitromethane to give predominantly the syn congeners 6 followed by a Nef oxidation and cyclization to afford lactone acetals 8, which are reduced and cyclized to give 2.

  DOI：

  10.1021/ol052554i

文献信息

• Diastereoselective synthesis of dimethyl cyclopropane-1,1-dicarboxylates from a γ-alkoxy-alkylidene malonate and sulfur and phosphorus ylides
  作者：Alain Krief、Laurent Provins、Alexandre Froidbise

  DOI：10.1016/s0040-4039(97)10822-x

  日期：1998.3

  Isopropylidene diphenylsulfurane and isopropylidene triphenylphosphorane react by the same (Re) face of the alkylidene malonate derived from the acetonide of (d)-glyceraldehyde to produce almost exclusively a single diastereoisomer of the corresponding dimethyl cyclopropane-1,1-dicarboxylate.

  异亚丙基二苯基硫烷与异亚丙基三苯基膦烷在亚烷基丙二酸酯的相同（Re）面上反应，该亚烷基丙二酸酯衍生自（d）-甘油醛的乙炔化物，几乎只生成相应的二甲基环丙烷-1,1-二羧酸酯的单一非对映体。
• Asymmetric Synthesis of Cyclopropane-1,1-Dicarboxylates from a γ-Alkoxy-Alkylidenemalonate
  作者：Alain Krief、Laurent Provins、Alexandre Froidbise

  DOI：10.1055/s-1999-3173

  日期：1999.12

  2-Metallo-2-sulfonylpropanes and 2-metallo-2-nitropropanes react with the dimethyl alkylidenemalonate derived from the acetonide of d-glyceraldehyde to produce the Michael adduct or the corresponding dimethyl cyclopropane-1,1-dicarboxylate. The nature of the product formed and the relative configuration of the cyclopropane derivative depends upon the nature of the leaving group and the conditions used (solvent and counter ion).

  2-Metallo-2-sulfonylpropanes 和 2-Metallo-2-nitropropanes 与 d-glyceraldehyde 的丙酮衍生物亚烷基丙二酸二甲酯发生反应，生成迈克尔加合物或相应的环丙烷-1,1-二甲酸二甲酯。生成产物的性质和环丙烷衍生物的相对构型取决于离去基团的性质和使用条件（溶剂和反离子）。
• Stereochemically Controlled Cyclopropanation of (<i>S</i>)-Glyceraldehyde Acetonide-Derived Olefins. Synthesis of (2<i>S</i>,1‘<i>R</i>,2‘<i>R</i>,3‘<i>R</i>)-2-(2‘,3‘-Dicarboxycyclopropyl)glycine
  作者：Dawei Ma、Yeyu Cao、Yi Yang、Dongliang Cheng

  DOI：10.1021/ol990598j

  日期：1999.7.1

  [GRAPHICS]The reactions of ethyl (dimethylsulfuranylidene)acetate or other related sulfonium ylides with olefins 1 derived from (S)-glyceraldehyde acetonide provide cyclopropanation products in good to excellent diastereoselectivity. On the basis of this reaction, a new synthetic protocol for (2S,1'R,2'R,3'R)-2-(2',3'-dicarboxycyclopropyl)glycine (L-DCG-IV), an isotype-selective agonist of metabotropic glutamate receptors, is developed.
• METHOD FOR THE PREPARATION OF HEXAHYDRO-FURO 2,3-B FURAN-3-OL
  申请人：Tibotec Pharmaceuticals

  公开号：EP1448567B1

  公开（公告）日：2009-12-30
• Stereoselective and Efficient Synthesis of (3<i>R</i>,3a<i>S</i>,6a<i>R</i>)-Hexahydrofuro[2,3-<i>b</i>]furan-3-ol
  作者：Peter J. L. M. Quaedflieg、Bart R. R. Kesteleyn、Piet B. T. P. Wigerinck、Nicolaas M. F. Goyvaerts、Robert Jan Vijn、Constantinus S. M. Liebregts、Jaap H. M. H. Kooistra、Claudia Cusan

  DOI：10.1021/ol052554i

  日期：2005.12.1

  [GRAPHICS]Two short and efficient synthesis routes have been developed for bis-THF-alcohol 2, a key building block of the investigational HIV protease inhibitor TMC114 (1). Using S-2,3-O-isopropylideneglyceraldehyde (4) as the source of chirality, both routes are based on a diastereoselective Michael addition of nitromethane to give predominantly the syn congeners 6 followed by a Nef oxidation and cyclization to afford lactone acetals 8, which are reduced and cyclized to give 2.