methyl 3α,4α-isopropylidenedioxy-5β-(iodomethyl)cyclohex-1-ene-1-carboxylate | 134039-38-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 3α,4α-isopropylidenedioxy-5β-(iodomethyl)cyclohex-1-ene-1-carboxylate
• 英文别名: methyl 3α,4α-isopropylidene-5β-iodomethylcyclohex-1-ene-1-carboxylate
• CAS: 134039-38-6
• 化学式: C₁₂H₁₇IO₄
• 分子量: 352.169
• InChiKey: DAFZYFLOJYNDBM-KXUCPTDWSA-N

物化性质

• 沸点：
  368.2±42.0 °C(Predicted)
• 密度：
  1.531±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.06
• 重原子数：
  17.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  44.76
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  methyl 3α,4α-isopropylidenedioxy-5β-(iodomethyl)cyclohex-1-ene-1-carboxylate 在 N,N-二甲基丙烯基脲 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 18.0h， 生成 methyl 3α,4α-isopropylidenedioxy-5β-<2-methoxycarbonylprop-1-en-3-yl>-cyclohex-1-ene-1-carboxylate
  参考文献：
  名称：

  5-烯丙基丙酮基shi草酸的5-亚甲基类似物的合成

  摘要：

  由3-α，4α-异亚丙基甲基合成（±）-3-（1-羧基-3α，4α-二羟基环己基-1-en-5β-基）-2-亚甲基丙酸，5-烯丙基丙酮基shi草酸的亚甲基类似物描述了-5β-碘甲基环己-1-烯-1-羧酸酯。起始化合物获自（±）-甲基高古草酸酯。此外，高巴果酸甲酯的两种对映异构体均由1- t丁氧基羰基1,2-二氢吡啶的Diels-Alder环加成反应和Oppolzer的10,2-苏丹草的N-丙烯酰基衍生物合成。

  DOI：

  10.1016/s0040-4020(01)85625-8
• 作为产物：
  描述：

  methyl 5-cyclohexa-1,3-diene-1-carboxylate 在 18-冠醚-6 、 sodium hydride 、 三乙胺 、 三氟乙酸 、 potassium iodide 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 212.58h， 生成 methyl 3α,4α-isopropylidenedioxy-5β-(iodomethyl)cyclohex-1-ene-1-carboxylate
  参考文献：
  名称：

  Synthesis of 5-homoshikimic acid and some fluorinated derivatives as potential inhibitors of 5-enolpyruvylshikimate-3-phosphate synthase

  摘要：

  The synthesis of (+/-)-5-homoshikimic acid, its 5-fluoromethyl and difluoromethyl analogues are described from the cycloadducts of 5,6-dihydro-1-(t)butyloxycarbonylpyridine and methyl acrylate. The adducts on ring opening afford methyl 5-(t)butoxycarbonylmethyl-5,6-di-hydrobenzoate, which may be 3,4-cis-dihydroxylated and converted in a series of steps into the title compounds

  DOI：

  10.1016/s0040-4020(01)89449-7

文献信息

• Synthesis of (±)-homogabaculine and (±)-homoshikimic acid
  作者：Malcolm M. Campbell、Mary F. Mahon、Malcolm Sainsbury、Philip A. Searle、Gareth M. Davies

  DOI：10.1016/s0040-4039(00)92128-2

  日期：1991.2

  Syntheses of homogabaculine and homoshikimic acid are described utilising the base mediated ring opening of the cycloadducts of methyl acrylate and N-carbamoyl-1,2-dihydropyridines.
• Synthesis of methyl (−)-homogabaculinate and a carba analogue of 5-enolpyruvylshikimic acid
  作者：Malcolm M. Campbell、Malcolm Sainsbury、Philip A. Searle、Gareth M. Davies

  DOI：10.1016/s0040-4039(00)79846-7

  日期：1992.5

  The synthesis of (+/-)-3-[1-carboxy-3-alpha-4-alpha-dihydroxycyclohex-1-en-5-beta-yl]-2-methylenepropionic acid, a carba analogue of 5-enolpyruvylshikimic acid from methyl (+/-)-homogabaculinate is described. In addition, both enantiomers of methyl homogabaculinate have been obtained from the Diels Alder reaction of 1-tert-butoxy-carbonyl-1,2-dihydropyridine and the N-acryloyl derivative of Oppolzer's bomane 10,2-sultam.
• Synthesis of 5-homoshikimic acid and some fluorinated derivatives as potential inhibitors of 5-enolpyruvylshikimate-3-phosphate synthase
  作者：Malcolm M. Campbell、Mary F. Mahon、Malcolm Sainsbury、Philip A. Searle、Gareth M. Davies

  DOI：10.1016/s0040-4020(01)89449-7

  日期：——

  The synthesis of (+/-)-5-homoshikimic acid, its 5-fluoromethyl and difluoromethyl analogues are described from the cycloadducts of 5,6-dihydro-1-(t)butyloxycarbonylpyridine and methyl acrylate. The adducts on ring opening afford methyl 5-(t)butoxycarbonylmethyl-5,6-di-hydrobenzoate, which may be 3,4-cis-dihydroxylated and converted in a series of steps into the title compounds
• Synthesis of a 5-methylene analogue of 5-enolpyruvylshikimic acid
  作者：Malcolm M. Campbell、Hélèna S. Rabiasz、Malcolm Sainsbury、Philip A. Searle、Gareth M. Davies

  DOI：10.1016/s0040-4020(01)85625-8

  日期：1992.1

  The synthesis of (±)-3-(1-carboxy-3α,4α-dihydroxycyclohex-1-en-5β-yl)-2-methylidenepropionic acid, a methylene analogue of 5-enolpyruvylshikimic acid, from methyl 3α,4α-isopropylidene-5β-iodomethylcyclohex-1-ene-1-carboxylate is described. The starting compound is obtained from (±)-methyl homogabaculate. In addition, both enantiomers of methyl homogabacuate have been synthesised from a Diels-Alder

  由3-α，4α-异亚丙基甲基合成（±）-3-（1-羧基-3α，4α-二羟基环己基-1-en-5β-基）-2-亚甲基丙酸，5-烯丙基丙酮基shi草酸的亚甲基类似物描述了-5β-碘甲基环己-1-烯-1-羧酸酯。起始化合物获自（±）-甲基高古草酸酯。此外，高巴果酸甲酯的两种对映异构体均由1- t丁氧基羰基1,2-二氢吡啶的Diels-Alder环加成反应和Oppolzer的10,2-苏丹草的N-丙烯酰基衍生物合成。