6-iodo-1,2-O-isopropylidenehexane-1,2-diol | 106681-40-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-iodo-1,2-O-isopropylidenehexane-1,2-diol
• 英文别名: 1,2-O-isopropylidene-6-iodohexane-1,2-diol；4-(4-iodobutyl)-2,2-dimethyl-1,3-dioxolane
• CAS: 106681-40-7
• 化学式: C₉H₁₇IO₂
• 分子量: 284.137
• InChiKey: CIPKTVUAIQHALU-UHFFFAOYSA-N

物化性质

• 沸点：
  87 °C(Press: 0.1 Torr)
• 密度：
  1.430±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.74
• 重原子数：
  12.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  18.46
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  6-iodo-1,2-O-isopropylidenehexane-1,2-diol 在 palladium on activated charcoal 吡啶 、 甲醇 、 4-二甲氨基吡啶 、 sodium azide 、 氢气 、 sodium methylate 、 sodium hydride 、 三氟乙酸 、 zinc dibromide 作用下， 以 甲醇 、 二氯甲烷 、 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 33.83h， 生成 methyl 4-O-(5-azido-9-α-D-glucopyranosyloxy-7-thianonyl)-α-D-glucopyranoside
  参考文献：
  名称：

  Spacer-modified oligosaccharides with basic anchoring groups are inhibitors for endo-glycanases: Porcine pancreatic alpha-amylase as model enzyme

  摘要：

  By coupling methyl 2,3,6-tri-O-acetyl-4-O-(5-azido-6-p-tolysulfonyloxyhexyl)-alpha-D-glucopyranoside with 2-benzoylthioethyl 2,3,4,6-tetra-O-acetyl-alpha-D-glucopyranoside, a spacer-modified disaccharide derivative, methyl 4-O-(5-azido-9-alpha-D-glucopyranosyloxy-7-thianonyl)-alpha-D-glucopyranoside, was obtained and then enzymatically glucosylated to yield the spacer-modified tri- and tetra-saccharide methyl 4-O-(5-azido-9-alpha-maltosyloxy-7-thianonyl)-alpha-D-glucopyranoside and methyl 4-O-(5-azido-9-alpha-maltotriosyloxy-7-thianonyl)-alpha-D-glucopyranoside, respectively, the extended spacer spanning the length of two (1 --> 4)-linked pyranosyl units. The corresponding amines methyl 4-O-(5-amino-9-alpha-D-glucopyranosyloxy-7-thianonyl)-alpha-D-glucopyranoside, methyl 4-O-(5-amino-9-alpha-maltosyloxy-7-thianonyl)-alpha-D-glucopyranoside and methyl 4-O-(5-amino-9-alpha-maltotriosyloxy-7-thianonyl)-alpha-D-glucopyranoside, obtained by catalytic reduction, carry the basic functionality in a spacer position to allow ionic interaction with a catalytically active acidic group in porcine pancreatic alpha-amylase (PPA). Optimal inhibition of enzymic activity is by methyl 4-O-(5-amino-9-alpha-maltosyloxy-7-thianonyl)-alpha-D-glucopyranoside where three of the five subsites are occupied by glucosyl units and the spacer spanning the remaining subsites positions the amino group near the catalytic site.

  DOI：

  10.1016/0008-6215(95)00089-c
• 作为产物：
  描述：

  4-(2,2-dimethyl-1,3-dioxolane-4-yl)-1-butanol 在 吡啶 、 sodium iodide 作用下， 以 丙酮 为溶剂， 反应 7.0h， 生成 6-iodo-1,2-O-isopropylidenehexane-1,2-diol
  参考文献：
  名称：

  Pyrroles as terminators in cationic cyclizations. The preparation of 5,6,7,8-tetrahydroindolizidines and 6,7,8,9-tetrahydro-5H-pyrrolo[1,2-a]azepines

  摘要：

  DOI：

  10.1021/jo00381a021

文献信息

• TANIS S. P.; RAGGON J. W., J. ORG. CHEM., 52,(1987) N 5, 819-827
  作者：TANIS S. P.、 RAGGON J. W.

  DOI：——

  日期：——
• Pyrroles as terminators in cationic cyclizations. The preparation of 5,6,7,8-tetrahydroindolizidines and 6,7,8,9-tetrahydro-5H-pyrrolo[1,2-a]azepines
  作者：Steven P. Tanis、Jeffrey W. Raggon

  DOI：10.1021/jo00381a021

  日期：1987.3
• Spacer-modified oligosaccharides with basic anchoring groups are inhibitors for endo-glycanases: Porcine pancreatic alpha-amylase as model enzyme
  作者：Jochen Lehmann、Markus Schmidt-Schuchardt

  DOI：10.1016/0008-6215(95)00089-c

  日期：1995.10

  By coupling methyl 2,3,6-tri-O-acetyl-4-O-(5-azido-6-p-tolysulfonyloxyhexyl)-alpha-D-glucopyranoside with 2-benzoylthioethyl 2,3,4,6-tetra-O-acetyl-alpha-D-glucopyranoside, a spacer-modified disaccharide derivative, methyl 4-O-(5-azido-9-alpha-D-glucopyranosyloxy-7-thianonyl)-alpha-D-glucopyranoside, was obtained and then enzymatically glucosylated to yield the spacer-modified tri- and tetra-saccharide methyl 4-O-(5-azido-9-alpha-maltosyloxy-7-thianonyl)-alpha-D-glucopyranoside and methyl 4-O-(5-azido-9-alpha-maltotriosyloxy-7-thianonyl)-alpha-D-glucopyranoside, respectively, the extended spacer spanning the length of two (1 --> 4)-linked pyranosyl units. The corresponding amines methyl 4-O-(5-amino-9-alpha-D-glucopyranosyloxy-7-thianonyl)-alpha-D-glucopyranoside, methyl 4-O-(5-amino-9-alpha-maltosyloxy-7-thianonyl)-alpha-D-glucopyranoside and methyl 4-O-(5-amino-9-alpha-maltotriosyloxy-7-thianonyl)-alpha-D-glucopyranoside, obtained by catalytic reduction, carry the basic functionality in a spacer position to allow ionic interaction with a catalytically active acidic group in porcine pancreatic alpha-amylase (PPA). Optimal inhibition of enzymic activity is by methyl 4-O-(5-amino-9-alpha-maltosyloxy-7-thianonyl)-alpha-D-glucopyranoside where three of the five subsites are occupied by glucosyl units and the spacer spanning the remaining subsites positions the amino group near the catalytic site.