(1S*,2S*)-1-Cyclohexyl-2-ethenyl-2,6-dimethylhept-5-en-1-ol | 84363-95-1

• 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: (1S*,2S*)-1-Cyclohexyl-2-ethenyl-2,6-dimethylhept-5-en-1-ol
• 英文别名: (1S,2S)-1-cyclohexyl-2-ethenyl-2,6-dimethylhept-5-en-1-ol
• CAS: 84363-95-1；84363-96-2
• 化学式: C₁₇H₃₀O
• 分子量: 250.425
• InChiKey: JPZQVDLNJXIUJI-DLBZAZTESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  geranyl tributyltin 、 环己烷基甲醛 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 以67%的产率得到(1S*,2S*)-1-Cyclohexyl-2-ethenyl-2,6-dimethylhept-5-en-1-ol
  参考文献：
  名称：

  通过烯丙基金属的立体选择性无环合成：路易斯酸催化烯丙基加成到醛的结构依赖性

  摘要：

  路易斯酸催化烯丙基锡与醛在 -78 °C 下的反应提供具有高立体选择性的高烯丙醇；2-烯基锡通常优先提供赤/苏比大于12/1的赤加合物，而从E-肉桂锡只能获得苏加加合物。

  DOI：

  10.1246/cl.1982.1299

文献信息

• Stereospecificity in the Lewis acid promoted allylation reaction of 3,3-disubstituted allyltins toward aldehydes
  作者：Yutaka Nishigaichi、Akio Takuwa

  DOI：10.1016/s0040-4039(98)80032-4

  日期：1999.1

  The Lewis acid-promoted reaction of 3,3-disubstituted allyltins toward aldehydes was found to be stereospecific; the (E)-reagent gave syn-products and the (Z)-one gave anti-products. This is in contrast to that of 3-mono-substituted congeners which are known to react syn-stereoselectively regardless of their double bond geometry. The reaction was assumed to proceed via an acyclic syn-synclinal transition

  发现3，3-二取代的烯丙基锡与路易斯的路易斯酸促进的反应是立体特异性的。（E）-试剂产生顺产物，（Z）-一个产生反产物。这与已知的3-单取代同源物相反，所述3-单取代同源物无论其双键的几何形状如何都可进行顺-立体选择性反应。假定该反应是通过无环顺向过渡态进行的。
• Chromium(II)-Mediated Stereodivergent Additions of Allylic Phosphates and Halides to Aldehydes
  作者：Stefan Nowotny、Charles E. Tucker、Carole Jubert、Paul Knochel

  DOI：10.1021/jo00114a026

  日期：1995.5

  The addition of gamma-disubstituted allylchromium(III) reagents to aldehydes proceeds in a stereodivergent manner, in contrast to the case of gamma-monosubstituted allylchromium(III) species. The method allows the preparation of a variety of homoallylic alcohols bearing a quaternary center of defined relative configuration in the alpha-position. The preparation of both stereomeric homoallylic alcohols 13 is possible by using either of the two (E)- or (Z)-allylic precursors. The reaction has been extended to a gamma-monosubstituted beta-(trimethylsilyl)allylic system. The intermediate allylic chromium(III) reagents can be conveniently prepared from the corresponding phosphates (or chlorides) in DMPU or THF in the presence of catalytic amounts of LiI.
• STEREOSELECTIVE ACYCLIC SYNTHESIS VIA ALLYLMETALS: STRUCTURAL DEPENDENCE IN A LEWIS-ACID CATALYZED ADDITION OF ALLYLTINS TO ALDEHYDES
  作者：Masato Koreeda、Yoshio Tanaka

  DOI：10.1246/cl.1982.1299

  日期：1982.8.5

  Lewis-acid catalyzed reaction of allyltins with aldehydes at −78 °C provide homoallyl alcohols with high stereoselectivity; 2-alkenyltins in general provide erythro adducts preferentially with an erythro/threo ratio greater than 12/1, whereas only threo adducts can be obtained from E-cinnamyltins.

  路易斯酸催化烯丙基锡与醛在 -78 °C 下的反应提供具有高立体选择性的高烯丙醇；2-烯基锡通常优先提供赤/苏比大于12/1的赤加合物，而从E-肉桂锡只能获得苏加加合物。