1-cyclohexyl-2-methyl-1,3-propane diol

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-cyclohexyl-2-methyl-1,3-propane diol
• 英文别名: 1-cyclohexyl-2-methylpropane-1,3-diol
• 化学式: C₁₀H₂₀O₂
• 分子量: 172.268
• InChiKey: VYZBHLWIWOZNBP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-cyclohexyl-2-methyl-1,3-propane diol 在 sodium hypochlorite 、 溶剂黄146 作用下， 反应 1.0h， 以93%的产率得到3-hydroxy-1-cyclohexyl-2-methyl-1-propanone
  参考文献：
  名称：

  BCl₃- and TiCl₄-Mediated Reductions of β-Hydroxy Ketones

  摘要：

  Syn-selective reduction protocols for beta-hydroxy ketones are described exploiting the intermediacy of titanium and boron chelates derived from TiCl4 and BCl3, respectively, Reductions are conducted at -78 degrees C in CH2Cl2 using a wide range of CH2Cl2-soluble reducing agents, Added acid-scavenging agents are detrimental to reaction selectivity, An A((1,3))-like interaction involving the stereocenter responsible for asymmetric induction provides conformational biasing of the intermediate chelates necessary for high diastereoselectivity.

  DOI：

  10.1021/jo951549x
• 作为产物：
  描述：

  3-环己基-3-羟基-2-甲基丙酸乙酯 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 2.0h， 以80%的产率得到1-cyclohexyl-2-methyl-1,3-propane diol
  参考文献：
  名称：

  BCl₃- and TiCl₄-Mediated Reductions of β-Hydroxy Ketones

  摘要：

  Syn-selective reduction protocols for beta-hydroxy ketones are described exploiting the intermediacy of titanium and boron chelates derived from TiCl4 and BCl3, respectively, Reductions are conducted at -78 degrees C in CH2Cl2 using a wide range of CH2Cl2-soluble reducing agents, Added acid-scavenging agents are detrimental to reaction selectivity, An A((1,3))-like interaction involving the stereocenter responsible for asymmetric induction provides conformational biasing of the intermediate chelates necessary for high diastereoselectivity.

  DOI：

  10.1021/jo951549x

文献信息

• Rapid and Stereochemically Flexible Synthesis of Polypropionates: Super-Silyl-Governed Aldol Cascades
  作者：Patrick B. Brady、Hisashi Yamamoto

  DOI：10.1002/anie.201108325

  日期：2012.2.20

  Polypropionates made EZ: The E/Z geometry of tris(trimethylsilyl)silyl super silyl enol ethers derived from propionaldehyde controls diastereoselectivity in the aldehyde crossed‐aldol reaction. These silyl enol ethers can participate in polyaldol cascade reactions, thus allowing the one‐pot synthesis of four different dipropionate stereotetrads (see scheme), and polyketides bearing up to five contiguous

  聚丙制成EZ：该ë / ž三（三甲基硅烷基）甲硅烷基超级的几何甲硅烷基烯醇醚从醛交叉醛醇缩合反应的控制丙醛衍生非对映选择性。这些甲硅烷基烯醇醚可以参与聚醛醇级联反应，从而允许一锅合成四种不同的二丙酸酯立体四分体（见方案），以及带有多达五个连续立体中心的聚酮化合物。
• Aldol reactions on solid phase. Sc(OTf)3-Catalyzed aldol reactions of polymer-supported silyl enol ethers with aldehydes providing convenient methods for the preparation of 1,3-diol, β-hydroxy carboxylic acid, and β-hydroxy aldehyde libraries
  作者：Shü Kobayashi、Iwao Hachiya、Masaru Yasuda

  DOI：10.1016/0040-4039(96)01158-6

  日期：1996.7

  Aldol reactions on solid phase have been achieved. In the presence of a catalytic amount of scandium triflate (Sc(OTf)3), polymer-supported silyl enol ethers reacted with aldehydes to afford the corresponding β-hydroxy thioester derivatives, which were reduced to 1,3-diol and β-hydroxy aldehyde derivatives, or hydrolyzed to β-hydroxy carboxylic acid derivatives.

  已经实现了固相上的醛醇缩合反应。在催化量的三氟甲磺酸scan（Sc（OTf）3）存在下，聚合物负载的甲硅烷基烯醇醚与醛反应，得到相应的β-羟基硫代酯衍生物，将其还原为1,3-二醇和β-羟基醛衍生物，或水解为β-羟基羧酸衍生物。
• Domino Hydroformylation/Enantioselective Cross-Aldol Addition
  作者：Olivier Abillard、Bernhard Breit

  DOI：10.1002/adsc.200700216

  日期：2007.8.6

  A domino hydroformylation/enantioselective cross-aldol reaction sequence is reported. Starting from simple alkenes enantiomerically pure aldol addition products, which represent valuable building blocks for polypropionate construction, can be obtained in a one-pot operation.

  报道了多米诺加氢甲酰化/对映选择性交叉羟醛反应序列。从简单的烯烃开始，对映体纯的羟醛加成产物可以代表一锅操作，代表了丙酸酯构建的重要组成部分。
• An Efficient One-Pot Synthesis of Oxetanes from 1,3-Diols
  作者：P. Picard、D. Leclercq、J. -P. Bats、J. Moulines

  DOI：10.1055/s-1981-29523

  日期：——
• Combined Proline–Surfactant Organocatalyst for the Highly Diastereo- and Enantioselective Aqueous Direct Cross-Aldol Reaction of Aldehydes
  作者：Yujiro Hayashi、Seiji Aratake、Tsubasa Okano、Junichi Takahashi、Tatsunobu Sumiya、Mitsuru Shoji

  DOI：10.1002/anie.200601156

  日期：2006.8.18