1-(1-methylallyl)cyclohexanol | 36971-11-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(1-methylallyl)cyclohexanol
• 英文别名: 1-(1-methyl-2-propenyl)cyclohexanol；1-(but-3-en-2-yl)cyclohexanol；1-(1-methylprop-2-en-1-yl)cyclohexan-1-ol；1-(1-methyl-2-propenyl)-1-cyclohexanol；1-(1-methylprop-2-enyl)cyclohexanol；Cyclohexanol, 1-(1-methyl-2-propenyl)-；1-but-3-en-2-ylcyclohexan-1-ol
• CAS: 36971-11-6
• 化学式: C₁₀H₁₈O
• 分子量: 154.252
• InChiKey: VIUDIHSMXOBGFG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-(1-methylallyl)cyclohexanol 在 正丁基锂 、 偶氮二异丁腈 、 三正丁基氢锡 、 potassium hydride 作用下， 以 苯 为溶剂， 反应 4.17h， 生成 cis-3,4-dimethyl-1-oxaspiro<4.5>decane
  参考文献：
  名称：

  Scope of alkoxymethyl radical cyclizations

  摘要：

  We have explored different aspects of the cyclization capability of alkoxymethyl radicals and report here a full account of our investigations. The required radicals were generated from (phenylseleno)methyl ethers (e.g., 6), which were prepared from homoallylic or bis-homoallylic alcohols by a two-step process. The alcohols were alkylated with (iodomethyl)tributylstannane. The stannanes were reacted with n-BuLi, and the resulting alpha-alkoxyanions were trapped with diphenyldiselenide to give the (phenylseleno)methyl ethers, which were stable to chromatography. When treated with tributyltin hydride, in the presence of a radical initiator, these precursors undergo a smooth cyclization to substituted tetrahydrofurans and tetrahydropyrans. Formation of the cyclization product was found to be the primary pathway even at relatively high tin hydride concentration. The diastereoselectivity of this cyclization was comparable to that observed in other radical cyclizations. The cis selectivity in cyclization of 6 increased gradually (up to 11:1) as the reaction temperature was lowered. The cyclization can be used for the synthesis of bicyclic and tricyclic compounds and can be incorporated in systems capable of tandem cyclizations.

  DOI：

  10.1021/jo00079a016
• 作为产物：
  描述：

  (2E)-1-(2-butenylsulfonyl)-4-methylbenzene 以14%的产率得到
  参考文献：
  名称：

  Cydnt Jonathan, Julla Mare, J. Chem. Soc. Chem. Commun, (1994) N 19, S 2261-2262

  摘要：

  DOI：

文献信息

• One-Pot Synthesis of Homoallylic Alcohols via a Facile Conversion of Allylic Alcohols into Allylic Iodides
  作者：Takaya Kanai、Shinji Irifune、Yasutaka Ishii、Masaya Ogawa

  DOI：10.1055/s-1989-27223

  日期：——

  Allylic alcohols were readily converted into allylic iodides by hydrogen iodide generated in situ from chlorotrimethylsilane/sodium iodide and water, or alcohols, under mild conditions. Displacement of allylic alcohols containing a terminal double bond gave allylic iodides accompanied by allylic rearrangement. This procedure has successfully been extended to a one-pot synthesis of homoallylic alcohols by carrying out successive Barbier type reactions.

  烯丙醇在温和条件下通过氯三甲基硅烷/碘化钠和水或醇现场生成的氢碘酸，可以方便地转化为烯丙基碘化物。具有末端双键的烯丙醇的取代反应会产生伴随烯丙基重排的烯丙基碘化物。这一方法已成功扩展为通过连续的巴比耶型反应，实现高烯丙醇的一锅法合成。
• Nickel-Catalyzed Reductive Allylation of Ketones with Allylic Carbonates
  作者：Wei Deng、Hegui Gong、Chenglong Zhao、Zhuozhen Tan、Zhuye Liang

  DOI：10.1055/s-0033-1339111

  日期：——

  Nickel-catalyzed efficient umpolung allylation of ketones with allylic carbonates in the presence of zinc powder is developed, which accommodates a variety of allylic and ketone substrates. Although chiral ligand is necessary for the transformation, no enantioselectivity was observed. Nickel-catalyzed efficient umpolung allylation of ketones with allylic carbonates in the presence of zinc powder is developed

  摘要 开发了在锌粉存在下，镍与酮的碳酸烯丙酯进行的镍催化的有效的烯丙基烯丙基化反应，可容纳各种烯丙基和酮的底物。尽管手性配体对于转化是必需的，但是未观察到对映选择性。 开发了在锌粉存在下，镍与酮的碳酸烯丙酯进行的镍催化的有效的烯丙基烯丙基化反应，可容纳各种烯丙基和酮的底物。尽管手性配体对于转化是必需的，但是未观察到对映选择性。
• A highly efficient addition of allylic bromides to carbonyl compounds promoted by Cp2TiCl2(cat.)/Zn system
  作者：Yu Ding、Gang Zhao

  DOI：10.1016/s0040-4039(00)74734-4

  日期：1992.12

  Aldehydes or ketones reacted with allylic bromides in the presence of Cp2TiCl2(cat.)/Zn system at room temperature to give homo-allylic alcohols in high yields.

  在室温下，在Cp 2 TiCl 2（cat。）/ Zn体系存在下，醛或酮与烯丙基溴反应，以高收率得到均烯丙基醇。
• [bmim][Br] as an Inexpensive and Efficient Medium for the Barbier-Type Allylation Reaction Using a Catalytic Amount of Indium: Mechanistic Studies
  作者：Papiya Dey、Mrunesh Koli、Dibakar Goswami、Anubha Sharma、Subrata Chattopadhyay

  DOI：10.1002/ejoc.201800043

  日期：2018.3.22

  The Barbier‐type allylation of aldehydes and ketones can be carried out with both unsubstituted and γ‐substituted allyl bromides using only a catalytic amount (0.1 equiv.) of In metal in [bmim][Br].

  醛和酮的Barbier型烯丙基化反应可以在[bmim] [Br]中仅使用催化量（0.1当量）的In金属与未取代和γ-取代的烯丙基溴进行。
• Allylation of Carbonyl Compounds by Allylic Acetates Using a Cobalt Halide as Catalyst
  作者：Corinne Gosmini、Paulo Gomes、Jacques Périchon

  DOI：10.1055/s-2003-40999

  日期：——

  In acetonitrile as solvent and in the presence of a simple cobalt halide as catalyst, the reduction by zinc dust of a mixture of aldehydes or ketones and allylic acetates affords the corresponding homoallylic alcohols in good yields.

  在乙腈作为溶剂和简单的卤化钴作为催化剂的存在下，通过锌粉还原醛或酮和烯丙基乙酸酯的混合物，以良好的收率得到相应的高烯丙基醇。