(1S,2R,6R,7S)-7-hydroxymethyl-2-methylbicyclo[4.1.0]hept-3-ene-1-carbaldehyde | 1376811-33-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1S,2R,6R,7S)-7-hydroxymethyl-2-methylbicyclo[4.1.0]hept-3-ene-1-carbaldehyde
• 英文别名: (1s,2r,6r,7s)-7-Hydroxymethyl-2-methylbicyclo-[4.1.0]hept-3-ene-1-carbaldehyde；(1S,2R,6R,7S)-7-(hydroxymethyl)-2-methylbicyclo[4.1.0]hept-3-ene-1-carbaldehyde
• CAS: 1376811-33-4
• 化学式: C₁₀H₁₄O₂
• 分子量: 166.22
• InChiKey: SJIDGWKZWJGQEE-DOLQZWNJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1S,2R,6R,7S)-7-hydroxymethyl-2-methylbicyclo[4.1.0]hept-3-ene-1-carbaldehyde 、 乙酸酐 在 吡啶 作用下， 以91%的产率得到(1S,2R,6R,7S)-1-formyl-2-methylbicyclo[4.1.0]-hept-3-en-7-yl acetate
  参考文献：
  名称：

  大黄苷及其类似物：II。A环中的侧链结构。红铝的具体作用

  摘要：

  侧链在亮氨酸苷类似物的修饰的A环中构建。Red-Al（1 S，2 R，6 R，7 S）-7-[（1 S，2 S）用X射线分析法测定-1,2-异丙基二烯二氧基-2-甲基丁-3-yn-1-基] -2-甲基双环[4.1.0]庚-3-烯-1-甲醛。

  DOI：

  10.1134/s1070428012040082
• 作为产物：
  描述：

  (1R,2R,6S)-2-methyl-6-[(2S)-oxiran-2-yl ]cyclohex-3-ene-1-carbonitrile 在 咪唑 、 正丁基锂 、 二异丙胺 、 红铝 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 0.5h， 生成 (1S,2R,6R,7S)-7-hydroxymethyl-2-methylbicyclo[4.1.0]hept-3-ene-1-carbaldehyde
  参考文献：
  名称：

  Eleuthesides and their analogs: III. Reaction of Red-Al with γ,δ-epoxy nitriles

  摘要：

  Oxiranyl-substituted cycloalkenecarbonitriles obtained by the Beckmann fragmentation of oximes derived from levoglucosenone adducts with 1,3-butadiene, isoprene, cyclohexadiene, and cyclopentadiene were subjected to Red-Al reduction with opening of the epoxide ring. The reactions with 1,3-butadiene, isoprene, and cyclohexadiene derivatives were accompanied by cyclopropane ring closure and reduction of the cyano group to aldehyde, whereas the cyclopentadiene derivative underwent hydrogenolysis of the oxirane fragment.

  DOI：

  10.1134/s1070428013070051

文献信息

• Eleuthesides and their analogs: III. Reaction of Red-Al with γ,δ-epoxy nitriles
  作者：Yu. A. Khalilova、O. Yu. Doronina、B. T. Sharipov、L. V. Spirikhin、F. A. Valeev

  DOI：10.1134/s1070428013070051

  日期：2013.7

  Oxiranyl-substituted cycloalkenecarbonitriles obtained by the Beckmann fragmentation of oximes derived from levoglucosenone adducts with 1,3-butadiene, isoprene, cyclohexadiene, and cyclopentadiene were subjected to Red-Al reduction with opening of the epoxide ring. The reactions with 1,3-butadiene, isoprene, and cyclohexadiene derivatives were accompanied by cyclopropane ring closure and reduction of the cyano group to aldehyde, whereas the cyclopentadiene derivative underwent hydrogenolysis of the oxirane fragment.
• Eleuthesides and their analogs: II. Side chain construction in the A ring. Specific action of Red-Al
  作者：Yu. A. Khalilova、O. Yu. Krasnoslobodtseva、B. T. Sharipov、L. V. Spirikhin、F. A. Valeev

  DOI：10.1134/s1070428012040082

  日期：2012.4

  Side chains were constructed in the modified A ring of eleutheside analog. The structure of the transformation product of 6-oxiranylcyclohex-3-ene-1-carbonitrile by the action of Red-Al, (1S,2R,6R,7S)-7-[(1S,2S)-1,2-isopropylidenedioxy-2-methylbut-3-yn-1-yl]-2-methylbicyclo[4.1.0]hept-3-ene-1-carbaldehyde, was determined by X-ray analysis.

  侧链在亮氨酸苷类似物的修饰的A环中构建。Red-Al（1 S，2 R，6 R，7 S）-7-[（1 S，2 S）用X射线分析法测定-1,2-异丙基二烯二氧基-2-甲基丁-3-yn-1-基] -2-甲基双环[4.1.0]庚-3-烯-1-甲醛。