(3S,4S)-1,6-dibromo-3,4-O-isopropylidenehexane-3,4-diol | 195731-29-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3S,4S)-1,6-dibromo-3,4-O-isopropylidenehexane-3,4-diol
• 英文别名: (4S,5S)-4,5-bis(2-bromoethyl)-2,2-dimethyl-1,3-dioxolane
• CAS: 195731-29-4
• 化学式: C₉H₁₆Br₂O₂
• 分子量: 316.033
• InChiKey: YRNQMWMOMTYXEQ-YUMQZZPRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (3S,4S)-1,6-dibromo-3,4-O-isopropylidenehexane-3,4-diol 在 正丁基锂 、 甲基磺酰胺 、 AD-mix-β 、 氨 、 sodium 、 sodium thiosulfate 作用下， 以 四氢呋喃 、 正己烷 、 二甲基亚砜 为溶剂， 反应 18.25h， 生成 1-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-6-{(4S,5S)-5-[6-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-3,4-dihydroxy-hexyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-hexane-3,4-diol
  参考文献：
  名称：

  Bidirectional and Convergent Routes to oligo(Tetrahydrofurans)

  摘要：

  AbstractOligo(tetrahydrofurans) (oligo‐THFs) 8–12 have been synthesised stereoselectively. Multiple Williamson reactions were used as key steps. While oligo‐THFs with an even number of THF rings like the bi‐THFs 8 and 9 as well as the tetra‐THFs 10 and 11 were obtained by a bidirectional strategy, the penta‐THF 12 with an odd number of THF rings was prepared by a convergent strategy with a sulfone–aldehyde coupling as connecting step. The oligo‐THF products are important structural features of natural (Annonaceae acetogenins) and non‐natural (artificial ion channels) products.

  DOI：

  10.1002/chem.19970030723
• 作为产物：
  描述：

  (3E)-1,6-二溴-3-己烯 在 Hydroquinone 1,4-phthalazinediyl diether 、 potassium dioxotetrahydroxoosmate(VI) 、 对甲苯磺酸 、 甲苯 、 potassium hexacyanoferrate(III) 作用下， 生成 (3S,4S)-1,6-dibromo-3,4-O-isopropylidenehexane-3,4-diol
  参考文献：
  名称：

  Synthesis and structure of C 2 -symmetric N -heterocyclic carbene complexes of palladium

  摘要：

  The first 9- and 11-membered cis and trans C-2-symmetric benzimidazol-2-ylidene palladium(11) complexes based on a trans-2,2-dimethyl-1,3-dioxalane backbone were synthesised and the configuration of the complexes was elucidated via NMR and X-ray crystallography. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.05.085

文献信息

• Wagner, Holger; Koert, Ulrich, Angewandte Chemie, 1994, vol. 106, # 18, p. 1939 - 1941
  作者：Wagner, Holger、Koert, Ulrich

  DOI：——

  日期：——