Toluene-4-sulfonic acid (1S,2R)-2-(2-ethoxy-ethoxy)-3,3-dimethyl-cyclobutylmethyl ester | 864915-08-2

• 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: Toluene-4-sulfonic acid (1S,2R)-2-(2-ethoxy-ethoxy)-3,3-dimethyl-cyclobutylmethyl ester
• 英文别名: [(1S,2R)-2-(2-ethoxyethoxy)-3,3-dimethylcyclobutyl]methyl 4-methylbenzenesulfonate
• CAS: 864915-08-2
• 化学式: C₁₈H₂₈O₅S
• 分子量: 356.483
• InChiKey: DRJRKYCHPPVNOM-DOTOQJQBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  24
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  70.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Toluene-4-sulfonic acid (1S,2R)-2-(2-ethoxy-ethoxy)-3,3-dimethyl-cyclobutylmethyl ester 在 盐酸 、 sodium hexamethyldisilazane 作用下， 以 四氢呋喃 、 二甲基亚砜 为溶剂， 生成 (1R,4S,5S)-4-[(E)-(1S,2S)-6-(tert-Butyl-diphenyl-silanyloxy)-1-hydroxy-2-methoxy-4-methyl-hex-3-enyl]-7,7-dimethyl-2-oxa-bicyclo[3.2.0]heptan-3-one
  参考文献：
  名称：

  Synthetic studies of pestalotiopsin A: asymmetric synthesis of the 2-oxabicyclo[3.2.0]heptane substructure

  摘要：

  A functionalized 2-oxabicyclo [3.2.0]heptan-3-one derivative, possessing all the skeletal carbons of pestalotiopsin A, has been synthesized. For the preparation of intermediary cyclobutane derivatives in enantioenriched form, the Lewis acid-catalyzed [2+2] cycloaddition of N-propiolated Oppoizer's camphorsultam with dimethylketene bis(trimethylsilyl) acetal followed by a stereo-selective 1,4-hydride addition/protonation, has been developed. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.06.133
• 作为产物：
  描述：

  (2R)-N-[3,3-dimethyl-4,4-bis(trimethylsilyloxy)cyclobut-1-enecarbonyl]-bornane-10,2-sultam 在 4-二甲氨基吡啶 、 lithium aluminium tetrahydride 、 4-甲基苯磺酸吡啶 、 L-Selectride 、 三乙胺 作用下， 以 乙醚 、 二氯甲烷 、 甲苯 为溶剂， 生成 Toluene-4-sulfonic acid (1S,2R)-2-(2-ethoxy-ethoxy)-3,3-dimethyl-cyclobutylmethyl ester
  参考文献：
  名称：

  Synthetic studies of pestalotiopsin A: asymmetric synthesis of the 2-oxabicyclo[3.2.0]heptane substructure

  摘要：

  A functionalized 2-oxabicyclo [3.2.0]heptan-3-one derivative, possessing all the skeletal carbons of pestalotiopsin A, has been synthesized. For the preparation of intermediary cyclobutane derivatives in enantioenriched form, the Lewis acid-catalyzed [2+2] cycloaddition of N-propiolated Oppoizer's camphorsultam with dimethylketene bis(trimethylsilyl) acetal followed by a stereo-selective 1,4-hydride addition/protonation, has been developed. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.06.133

文献信息

• Synthetic studies of pestalotiopsin A: asymmetric synthesis of the 2-oxabicyclo[3.2.0]heptane substructure
  作者：Ken-ichi Takao、Hiroshi Saegusa、Tomohiro Tsujita、Takenori Washizawa、Kin-ichi Tadano

  DOI：10.1016/j.tetlet.2005.06.133

  日期：2005.8

  A functionalized 2-oxabicyclo [3.2.0]heptan-3-one derivative, possessing all the skeletal carbons of pestalotiopsin A, has been synthesized. For the preparation of intermediary cyclobutane derivatives in enantioenriched form, the Lewis acid-catalyzed [2+2] cycloaddition of N-propiolated Oppoizer's camphorsultam with dimethylketene bis(trimethylsilyl) acetal followed by a stereo-selective 1,4-hydride addition/protonation, has been developed. (c) 2005 Elsevier Ltd. All rights reserved.