(1S,2S)-2-(Diethoxy-phosphoryl)-2-((S)-toluene-4-sulfinyl)-cyclopropanecarboxylic acid ethyl ester | 583827-30-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (1S,2S)-2-(Diethoxy-phosphoryl)-2-((S)-toluene-4-sulfinyl)-cyclopropanecarboxylic acid ethyl ester
• 英文别名: ethyl (1S,2S)-2-diethoxyphosphoryl-2-[(S)-(4-methylphenyl)sulfinyl]cyclopropane-1-carboxylate
• CAS: 583827-30-9
• 化学式: C₁₇H₂₅O₆PS
• 分子量: 388.422
• InChiKey: DELLJOYXJLBWEV-RTNKVPBISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  25
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  98.1
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (1S,2S)-2-(Diethoxy-phosphoryl)-2-((S)-toluene-4-sulfinyl)-cyclopropanecarboxylic acid ethyl ester 在 锂硼氢 、 甲基碘化镁 、 偶氮二甲酸二异丙酯 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 为溶剂， 反应 20.0h， 生成 9-[[(1S,2R)-2-diethoxyphosphorylcyclopropyl]methyl]purin-6-amine
  参考文献：
  名称：

  The first synthesis of enantiomerically pure cyclopropylphosphonate analogues of nucleotides via asymmetric cyclopropanation of chiral (1-diethoxyphosphoryl)vinyl p-tolyl sulfoxide

  摘要：

  (S)-(+)-(1-Diethoxyphosphoryl)vinyl p-tolyl sulfoxide undergoes cyclopropanation with ethyl (dimethylsulfuranylidene)acetate (EDSA) in a highly diastereoselective manner (facial stereoselectivity up to 12:1). The major diastereomer obtained in this reaction, (1S,2S)-(1-diethoxyphosphoryl-2-ethoxycarbonyl)cyclopropyl p-tolyl sulfoxide, was converted in three steps into enantiopure cyclopropylphosphonate analogues of purine nucleotides as the constrained forms of antiviral 1-alkenylphosphonic acid derivatives of purines. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00211-8
• 作为产物：
  描述：

  ethyl (dimethylsulfuranylidene)acetate 、 (+)-(S)-α-(diethoxyphosphoryl)vinyl p-tolyl sulfoxide 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 甲苯 为溶剂， 生成 (1S,2S)-2-(Diethoxy-phosphoryl)-2-((S)-toluene-4-sulfinyl)-cyclopropanecarboxylic acid ethyl ester 、 (1R,2S)-2-(Diethoxy-phosphoryl)-2-((S)-toluene-4-sulfinyl)-cyclopropanecarboxylic acid ethyl ester 、 (1S,2R)-2-(Diethoxy-phosphoryl)-2-((S)-toluene-4-sulfinyl)-cyclopropanecarboxylic acid ethyl ester 、 diethyl 1-p-tolylsulfinyl-2-carboethoxycyclopropane phosphonate
  参考文献：
  名称：

  The first synthesis of enantiomerically pure cyclopropylphosphonate analogues of nucleotides via asymmetric cyclopropanation of chiral (1-diethoxyphosphoryl)vinyl p-tolyl sulfoxide

  摘要：

  (S)-(+)-(1-Diethoxyphosphoryl)vinyl p-tolyl sulfoxide undergoes cyclopropanation with ethyl (dimethylsulfuranylidene)acetate (EDSA) in a highly diastereoselective manner (facial stereoselectivity up to 12:1). The major diastereomer obtained in this reaction, (1S,2S)-(1-diethoxyphosphoryl-2-ethoxycarbonyl)cyclopropyl p-tolyl sulfoxide, was converted in three steps into enantiopure cyclopropylphosphonate analogues of purine nucleotides as the constrained forms of antiviral 1-alkenylphosphonic acid derivatives of purines. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00211-8

文献信息

• Asymmetric synthesis of cyclopropyl phosphonates using chiral terpenyl sulfonium and selenonium ylides
  作者：Wanda H. Midura、Jacek Ścianowski、Anna Banach、Adrian Zając

  DOI：10.1016/j.tetasy.2014.10.002

  日期：2014.11

  The asymmetric cyclopropanation of a vinylphosphonate using optically active sulfonium and selenonium ylides derived from (−)-menthol and (+)-limonene was developed. The ylides were generated in situ by the reaction of the corresponding sulfonium or selenonium salt in the presence of potassium carbonate or DBU as a base. The transfer of the CHPh and CHCO2Et groups into the cyclopropane ring showed

  使用衍生自光学活性锍和硒鎓叶立德一个乙烯基膦的不对称环丙烷（ - ） -薄荷醇和（+） -苎烯的开发。由相应的锍或硒鎓盐在碳酸钾或DBU存在作为碱的反应在原位产生的内鎓盐。所述CHPh配合和CHCO的转移2的Et基团引入到环丙烷环呈中度非对映选择性和对映选择性优良（高达99：1）的反式-和CIS -products。苯基环丙基的绝对构型是基于相比于它们的甲苯基类似物分配。
• Asymmetric Cyclopropanation of Optically Active Vinyl Sulfoxides: A New Synthetic Approach to Biologically Active Compounds
  作者：Wanda H. Midura

  DOI：10.1080/10426500590911593

  日期：2005.3.2

  substituents on stereochemical course of cyclopropanation of vinyl sulfoxides with stabilized and nonstabilized ylides, as well as dependence on reaction conditions, was investigated. Application of optically active cyclopropanes obtained in the synthesis of conformationally constrained analogs of L-glutamic acid, the useful pharmacological tools in investigation of excitatory amino acid receptors, is presented

  摘要 研究了相邻取代基对乙烯基亚砜与稳定和非稳定叶立德环丙烷化立体化学过程的影响，以及对反应条件的依赖性。介绍了在合成受构象限制的 L-谷氨酸类似物中获得的光学活性环丙烷的应用，该类似物是研究兴奋性氨基酸受体的有用药理学工具。
• The first synthesis of enantiomerically pure cyclopropylphosphonate analogues of nucleotides via asymmetric cyclopropanation of chiral (1-diethoxyphosphoryl)vinyl p-tolyl sulfoxide
  作者：W Midura

  DOI：10.1016/s0957-4166(03)00211-8

  日期：2003.5.16

  (S)-(+)-(1-Diethoxyphosphoryl)vinyl p-tolyl sulfoxide undergoes cyclopropanation with ethyl (dimethylsulfuranylidene)acetate (EDSA) in a highly diastereoselective manner (facial stereoselectivity up to 12:1). The major diastereomer obtained in this reaction, (1S,2S)-(1-diethoxyphosphoryl-2-ethoxycarbonyl)cyclopropyl p-tolyl sulfoxide, was converted in three steps into enantiopure cyclopropylphosphonate analogues of purine nucleotides as the constrained forms of antiviral 1-alkenylphosphonic acid derivatives of purines. (C) 2003 Elsevier Science Ltd. All rights reserved.