(1R)-1-cyclohexyl-3-methylbut-3-en-1-ol | 151453-08-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1R)-1-cyclohexyl-3-methylbut-3-en-1-ol
• 英文别名: (R)-1-cyclohexyl-3-methyl-3-butene-1-ol；(R)-1-cyclohexyl-3-methylbut-3-en-1-ol
• CAS: 151453-08-6
• 化学式: C₁₁H₂₀O
• 分子量: 168.279
• InChiKey: JTCFUZHKTZXRTK-LLVKDONJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 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：

  (4R,6R)-2-cyclohexyl-4,6-dimethyl-1,3-dioxane 在 titanium(IV) isopropylate 、 氢氧化钾 、 四氯化钛 、 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 生成 (1R)-1-cyclohexyl-3-methylbut-3-en-1-ol
  参考文献：
  名称：

  通过缩醛模板的不对称合成。9.对烯丙基化反应的进一步研究。（-）-二氢肌oporone的制备

  摘要：

  已经开发了用于手性乙缩醛1与烯丙基三甲基硅烷（2，R'= H）以及与甲基烯丙基三甲基硅烷（2，R'= ME）的高收率偶联的程序，以提供其中新的手性中心为羟基醚3高度对映选择性地形成。通过除去手性助剂来生产高ee的均烯丙基醇4。

  DOI：

  10.1016/0040-4039(84)80038-6

文献信息

• Catalytic enantioselective Grignard Nozaki–Hiyama methallylation from the alcohol oxidation level: chloride compensates for π-complex instability
  作者：Abbas Hassan、Ian A. Townsend、Michael J. Krische

  DOI：10.1039/c1cc14392a

  日期：——

  Methallyl chloride serves as an efficient allyl donor in highly enantioselective Grignard Nozaki-Hiyama methallylations from the alcohol or aldehyde oxidation level via iridium catalyzed transfer hydrogenation. Under identical conditions, methallyl acetate does not react efficiently. Double methallylation of 1,3-propanediol provides the C(2)-symmetric adduct as a single enantiomer, as determined by

  在通过铱催化转移氢化从醇或醛氧化水平进行高度对映选择性格利雅野崎-Hiyama 甲基烯丙基化反应中，甲基烯丙基氯可作为有效的烯丙基供体。在相同条件下，乙酸甲烯丙酯不能有效反应。1,3-丙二醇的双甲基化提供 C(2)-对称加合物作为单个对映异构体，如 HPLC 分析所确定的。
• Scope and Limitations of the Scandium-Catalyzed Enantioselective Addition of Chiral Allylboronates to Aldehydes
  作者：Dennis G. Hall、Michel Gravel、Hugo Lachance、Xiaosong Lu

  DOI：10.1055/s-2004-822359

  日期：——

  Scandium triflate catalyzes the addition of camphor-derived allyl-, methallyl-, and crotylboronates to aldehydes to provide homoallylic alcohols with excellent diastereo- and enantioselectivity. Aromatic, aliphatic, and propargylic aldehydes can be used successfully in this system. Additional advantages of the camphor-diol allylboronates are their ease of synthesis, their availability in both enantiomeric forms, and their stability towards silica gel chromatography. The usefulness of this methodology is further demonstrated by the gram-scale synthesis of various homoallylic alcohols of high enantiomeric excess and by the concise synthesis of the phero­mone (4S)-2-methyloctan-4-ol.

  三氟甲磺酸钪催化从樟脑衍生的烯丙基、异烯丙基和克罗丁基硼酸酯与醛的加成反应，生成具有优异的反式选择性和对映体选择性的同烯丙醇。芳香族、脂肪族和炔基醛在该体系中均可成功使用。樟脑二醇烯丙基硼酸酯的其他优点包括合成方便、可获得两种对映体形式以及对硅胶柱层析的稳定性。该方法的实用性进一步体现在高对映体过量的各种同烯丙醇的克级合成以及信息素（4S)-2-甲基辛醇的简洁合成中。
• Asymmetric Catalysis of Nozaki−Hiyama Allylation and Methallylation with A New Tridentate Bis(oxazolinyl)carbazole Ligand
  作者：Masahiro Inoue、Takahiro Suzuki、Masahisa Nakada

  DOI：10.1021/ja021243p

  日期：2003.2.1

  the asymmetric catalysis of Nozaki-Hiyama allylation and methallylation. Various aldehydes were allylated or methallylated with good enantioselectivity (86-96%), and a key intermediate of calcitriol lactone synthesis was also obtained with excellent diastereoselectivity (97% de, 91%). The enantioselective reaction catalyzed by this Cr-ligand complex is applicable to a broad range of aldehydes and has

  这项工作描述了对 Nozaki-Hiyama 烯丙基化和甲基烯丙基化的不对称催化有效的新三齿配体的开发。各种醛以良好的对映选择性（86-96%）烯丙基化或甲基烯丙基化，并以优异的非对映选择性（97% de, 91%）获得骨化三醇内酯合成的关键中间体。由这种 Cr-配体配合物催化的对映选择性反应适用于广泛的醛类，在天然产物合成方面具有巨大潜力。这种配体的另一个显着特征是 Cr-配体复合物的稳定性，它在对映选择性反应后回收并循环两次，而不会降低对映选择性和产率。
• CATALYTIC ASYMMETRIC ALLYLATION REACTIONS: (S)-1-(PHENYLMETHOXY)-4-PENTEN-2-OL
  作者：Keck, Gary E.、Krishnamurthy, Dhileepkumar、Roush, William R.、Reilly, Melissa L.

  DOI：10.15227/orgsyn.075.0012

  日期：——
• Catalytic asymmetric allylation reactions. 3. Extension to methallylstannane, comparison of procedures, and observation of a nonlinear effect
  作者：Gary E. Keck、Dhileepkumar Krishnamurthy、Mark C. Grier

  DOI：10.1021/jo00076a005

  日期：1993.11

  Enantioselective additions of methallylstannanes to representative aldehydes with four chiral Lewis acid systems afford ee's of 84-99% using 10 mol % of catalyst. In one case, use of (R)-BINOL of 50% ee gave product with 88% ee.