(1R,2R,6S)-6-[(1R)-1-hydroxyethyl]-2-methylcyclohex-3-ene-1-carbonitrile | 1253968-88-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (1R,2R,6S)-6-[(1R)-1-hydroxyethyl]-2-methylcyclohex-3-ene-1-carbonitrile
• 英文别名: (1r,2r,6s)-6-[(1r)-1-Hydroxyethyl]-2-methyl-cyclohex-3-ene-1-carbonitrile
• CAS: 1253968-88-5
• 化学式: C₁₀H₁₅NO
• 分子量: 165.235
• InChiKey: KBHKQQDBHQTXNK-ZYUZMQFOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  44
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (1S)-2-chloro-1-[(1S,5R,6R)-6-cyano-5-methyl-cyclohex-3-en-1-yl]ethyl formate 在 红铝 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以94%的产率得到(1R,2R,6S)-6-[(1R)-1-hydroxyethyl]-2-methylcyclohex-3-ene-1-carbonitrile
  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: I. Synthesis of the base compound from levoglucosenone adduct with piperylene
  作者：Yu. A. Kondrova、O. Yu. Krasnoslobodtseva、L. V. Spirikhin、F. A. Valeev

  DOI：10.1134/s1070428010080063

  日期：2010.8

  and piperylene was converted into the corresponding oxime, and second-order Beckmann rearrangement of the latter, followed by treatment with a base, gave (1S,2R,6R)-6-(2-hydroxyethyl)-2-methylcyclohex-3-ene-1-carbaldehyde which was used in the synthesis of eleutheside analog. Conditions were found for opening of oxirane ring with formation of primary alcohol and simultaneous reduction of cyano group

  将左葡糖醛酮和间戊二烯的狄尔斯-阿尔德加合物转化为相应的肟，并对后者进行二阶贝克曼重排，然后用碱处理，得到（1 S，2 R，6 R）-6-（2-羟乙基）-2-甲基环己-3-烯-1-甲醛用于合成亮氨酸苷类似物。发现了在环氧乙烷环上开环，形成伯醇并通过Red-Al-H 2 O作用将氰基同时还原为醛的条件。