1-cyclohexyl-4-hydroxybutan-1-one | 107841-10-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-cyclohexyl-4-hydroxybutan-1-one
• 英文别名: 1-Cyclohexyl-4-hydroxy-1-butanone
• CAS: 107841-10-1
• 化学式: C₁₀H₁₈O₂
• 分子量: 170.252
• InChiKey: FMPJHFFKAILMGS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.9
• 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：

  1-cyclohexyl-4-hydroxybutan-1-one 在 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 methyl (E)-6-cyclohexyl-6-oxohex-2-enoate
  参考文献：
  名称：

  Structure–activity relationship of anti-malarial spongean peroxides having a 3-methoxy-1,2-dioxane structure

  摘要：

  In order to study the structure-activity relationship of anti-malarial spongean peroxides, several analogues concerning with the 6-methoxyacetyl moiety and the 3-pentyl residue in methyl 2-(3-methoxy-3-pentyl-1,2-dioxan-6-yl) acetate were synthesized and evaluated for anti-malarial activity. The tert-butyl ester analogue 14 showed stability in mouse serum and a high selectivity index against the malaria parasite, Plasmodium falciparum, and the citronellyl analogue 31 exhibited the strongest in vitro antimalarial activity among them, and the imidazole analogue 25 showed desirable in vivo anti-malarial activity against P. berghei infected mice. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.04.051
• 作为产物：
  描述：

  4-(cyclohexylhydroxymethyl)-2,2-dimethyl-1,3-oxathiane 3,3-dioxide 在 jones reagent 作用下， 以91%的产率得到1-cyclohexyl-4-hydroxybutan-1-one
  参考文献：
  名称：

  THE REACTION OF 2,2-DIMETHYL-4-LITHIO-1,3-OXATHIANE 3,3-DIOXIDE. GENERAL SYNTHESIS OF γ-HYDROXYKETONES

  摘要：

  2,2-二甲基-4-锂-1,3-氧杂噻烷3,3-二氧化物(2)与卤代烷和羰基化合物的反应顺利进行，得到4-取代的杂环。描述了利用 2 从醛合成 γ-羟基酮的一般方法。

  DOI：

  10.1246/cl.1986.961

文献信息

• 1,2-metallate rearrangements of α-alkoxyvinyl borates
  作者：Simon Birkinshaw、Philip Kocieński

  DOI：10.1016/0040-4039(91)80455-f

  日期：1991.11

  α-Alkoxyvinyl borates derived from reaction of 5-lithio-2,3-dihydrofuran with trialkylboranes rearrange by two different mechanisms depending on the reaction conditions.

  取决于反应条件，通过两种不同的机理使5-锂硫基-2,3-二氢呋喃与三烷基硼烷的反应衍生的α-烷氧基乙烯基硼酸酯重排。
• 2,2-Dimethyl-1,3-oxathiane 3,3-Dioxide: A γ-Hydroxypropyl Anion Equivalent
  作者：Kaoru Fuji、Yoshihide Usami、Yoshimitsu Kiryu、Manabu Node

  DOI：10.1055/s-1992-26246

  日期：——

  The reaction of 4-lithio-2,2-dimethyl-1,3-oxathiane 3,3-dioxide with various electrophiles is presented. Acylation of the anion provided labile 4-acyl-2, 2-dimethyl-1,3-oxathiane 3,3-dioxides which underwent desulfonation with silica gel to produce γ-hydroxy ketones with three carbon unit elongation. Thus, 4-lithio-2,2-dimethyl-1,3-oxathiane 3,3-dioxide was shown to be a useful synthetic equivalent of a γ-hydroxypropyl anion. Methyl esters proved to be the best acylating agents in this reaction. Synthetic utility of this carbon chain elongation was illustrated by the syntheses of dl-lanceol and dl-dihydrojasmone.

  4-锂-2,2-二甲基-1,3-噁硫烷-3,3-二氧化物与各种电亲体的反应结果被呈现。对阴离子的酰化提供了不稳定的4-酰基-2,2-二甲基-1,3-噁硫烷-3,3-二氧化物，这些化合物与硅胶脱磺反应，生成了具有三个碳单位延长的γ-羟基酮。因此，4-锂-2,2-二甲基-1,3-噁硫烷-3,3-二氧化物被证明是一种有用的γ-羟基丙基阴离子的合成等价物。甲基酯在这个反应中被证明是最佳的酰化试剂。这种碳链延长的合成实用性通过合成dl-兰索尔和dl-二氢茉莉酮得到了说明。
• A new method for the preparation of γ-hydroxy ketones: a formal total synthesis of (±)-lanceol
  作者：Kaoru Fuji、Manabu Node、Yoshihide Usami、Yoshimitsu Kiryu

  DOI：10.1039/c39870000449

  日期：——

  The reaction of methyl esters with 2,2-dimethyl-4-lithio-1,3-oxathiane 3,3-dioxide followed by treatment with silica gel affords γ-hydroxy ketones.

  甲酯与2,2-二甲基-4-硫代-1,3-氧杂蒽3,3-二氧化物反应，然后用硅胶处理，得到γ-羟基酮。
• Phenyliodine diacetate-mediated oxidative cleavage of cyclobutanols leading to γ-hydroxy ketones
  作者：Hiromichi Fujioka、Hideyuki Komatsu、Akihito Miyoshi、Kenichi Murai、Yasuyuki Kita

  DOI：10.1016/j.tetlet.2010.12.032

  日期：2011.3

  Oxidative cleavage of cyclobutanols using PIDA, which leads to efficient entry of gamma-hydroxy ketones, is described. When using 2-substituted cyclobutanols, gamma-substituted gamma-hydroxy ketones are obtained through regioselective C-C bond cleavage. (C) 2010 Elsevier Ltd. All rights reserved.
• FUJI, KAORU;NODE, MANABU;USAMI, YOSHIHIDE, CHEM. LETT., 1986, N 6, 961-962
  作者：FUJI, KAORU、NODE, MANABU、USAMI, YOSHIHIDE

  DOI：——

  日期：——