(1R,7S)-3-cyano-9,9-di-tert-butyl-2,8,10-trioxa-9-silabicyclo[5.4.0]undec-5-ene

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: (1R,7S)-3-cyano-9,9-di-tert-butyl-2,8,10-trioxa-9-silabicyclo[5.4.0]undec-5-ene
• 英文别名: (4aR,9aS)-2,2-ditert-butyl-4a,6,7,9a-tetrahydro-4H-[1,3,2]dioxasilino[5,4-b]oxepine-6-carbonitrile
• 化学式: C₁₆H₂₇NO₃Si
• 分子量: 309.481
• InChiKey: QBTCXMMHDMEUER-KFTPUPIBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.68
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  51.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4,6-O-di(tert-butyl)silanediyl-D-glucal 在 4-二甲氨基吡啶 、 三氟甲磺酸三甲基硅酯 、 diethylzinc 作用下， 以 吡啶 、 乙醚 、 正己烷 、 乙腈 为溶剂， 反应 6.33h， 生成 (1R,7S)-3-cyano-9,9-di-tert-butyl-2,8,10-trioxa-9-silabicyclo[5.4.0]undec-5-ene
  参考文献：
  名称：

  Formation of Seven-Membered Oxacycles through Ring Expansion of Cyclopropanated Carbohydrates

  摘要：

  The cyclopropanation and ring expansion of 4,6-O-(di-tert-butylsilanediyl)-D-glucal (1) to produce oxepanes have been investigated. Using catalytic amounts of TMSOTf and an excess of a silylated nucleophile, a wide range of substituted oxepanes have been synthesized. Good to excellent yields are obtained; however, only modest diastereoselectivity resulted. This new methodology should provide convenient access into the synthesis of optically active oxepanes.

  DOI：

  10.1021/jo970649v

文献信息

• Formation of Seven-Membered Oxacycles through Ring Expansion of Cyclopropanated Carbohydrates
  作者：John O. Hoberg

  DOI：10.1021/jo970649v

  日期：1997.9.1

  The cyclopropanation and ring expansion of 4,6-O-(di-tert-butylsilanediyl)-D-glucal (1) to produce oxepanes have been investigated. Using catalytic amounts of TMSOTf and an excess of a silylated nucleophile, a wide range of substituted oxepanes have been synthesized. Good to excellent yields are obtained; however, only modest diastereoselectivity resulted. This new methodology should provide convenient access into the synthesis of optically active oxepanes.