tert-butyl-[(1R)-2-[(4-methoxyphenyl)methoxy]-1-[(2R)-oxiran-2-yl]ethoxy]-dimethylsilane | 313677-45-1

• 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: tert-butyl-[(1R)-2-[(4-methoxyphenyl)methoxy]-1-[(2R)-oxiran-2-yl]ethoxy]-dimethylsilane
• CAS: 313677-45-1
• 化学式: C₁₈H₃₀O₄Si
• 分子量: 338.519
• InChiKey: SDKULJSRWSJWRD-IAGOWNOFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.0
• 重原子数：
  23
• 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：
  40.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  tert-butyl-[(1R)-2-[(4-methoxyphenyl)methoxy]-1-[(2R)-oxiran-2-yl]ethoxy]-dimethylsilane 在 palladium on activated charcoal 4-二甲氨基吡啶 、 正丁基锂 、 TEA 、 三氟化硼乙醚 、 四丁基氟化铵 、 氢气 、 potassium carbonate 、 三苯基膦 、 三丁基氧化锡 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 乙酸乙酯 、 甲苯 为溶剂， 反应 24.0h， 生成 (1R)-2-[(4-methoxyphenyl)methoxy]-1-[(2R,7R)-7-(phenylmethoxymethyl)oxepan-2-yl]ethanol
  参考文献：
  名称：

  Stereospecific synthesis of α,ω-cis- and α,ω-trans-disubstituted oxepanes

  摘要：

  An efficient and versatile method for the stereospecific construction of alpha,omega-cis- and alpha,omega-trans-disubstituted oxepane skeletons is described. Cyclization of the hydroxy epoxides promoted by a (Bu3Sn)(2)O/Zn(OTf)(2) system proceeded via an S(N)2 process and exo mode selectivity regardless of the configuration of the hydroxyl and the epoxy groups to provide the corresponding oxepanes in excellent yields. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)01344-7
• 作为产物：
  描述：

  (-)-2,3-O-亚异丙基-D-苏力糖醇 、 叔丁基二甲基氯硅烷 、 4-甲氧基氯苄 生成 tert-butyl-[(1R)-2-[(4-methoxyphenyl)methoxy]-1-[(2R)-oxiran-2-yl]ethoxy]-dimethylsilane
  参考文献：
  名称：

  Stereospecific synthesis of α,ω-cis- and α,ω-trans-disubstituted oxepanes

  摘要：

  An efficient and versatile method for the stereospecific construction of alpha,omega-cis- and alpha,omega-trans-disubstituted oxepane skeletons is described. Cyclization of the hydroxy epoxides promoted by a (Bu3Sn)(2)O/Zn(OTf)(2) system proceeded via an S(N)2 process and exo mode selectivity regardless of the configuration of the hydroxyl and the epoxy groups to provide the corresponding oxepanes in excellent yields. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)01344-7

文献信息

• The first total synthesis of (+)-rogioloxepane A
  作者：Ryuji Matsumura、Toshio Suzuki、Hisahiro Hagiwara、Takashi Hoshi、Masayoshi Ando

  DOI：10.1016/s0040-4039(00)02281-4

  日期：2001.2

  The first total synthesis of (+)-rogioloxepane A is described. The alpha,omega -trans-disubstituted oxepene skeleton was stereoselectively constructed via cyclization of the hydroxy epoxide promoted by the (Bu3Sn)(2)O/Zn(OTf)(2) system. The proposed configurations of 6R and 13R were confirmed through this synthetic study. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Stereospecific synthesis of α,ω-cis- and α,ω-trans-disubstituted oxepanes
  作者：Ryuji Matsumura、Toshio Suzuki、Kohki Sato、Takashi Inotsume、Hisahiro Hagiwara、Takashi Hoshi、Vijayendra P Kamat、Masayoshi Ando

  DOI：10.1016/s0040-4039(00)01344-7

  日期：2000.9

  An efficient and versatile method for the stereospecific construction of alpha,omega-cis- and alpha,omega-trans-disubstituted oxepane skeletons is described. Cyclization of the hydroxy epoxides promoted by a (Bu3Sn)(2)O/Zn(OTf)(2) system proceeded via an S(N)2 process and exo mode selectivity regardless of the configuration of the hydroxyl and the epoxy groups to provide the corresponding oxepanes in excellent yields. (C) 2000 Elsevier Science Ltd. All rights reserved.