(R)-6-Benzyloxymethyl-4-methyl-5,6- | 1224588-21-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (R)-6-Benzyloxymethyl-4-methyl-5,6-
• 英文别名: (2S)-4-methyl-2-(phenylmethoxymethyl)-2,3-dihydropyran-6-one
• CAS: 1224588-21-9
• 化学式: C₁₄H₁₆O₃
• 分子量: 232.279
• InChiKey: LAENAAGUUTWGCG-ZDUSSCGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R)-6-Benzyloxymethyl-4-methyl-5,6- 在 sodium tetrahydroborate 、 nickel (II) chloride hexahydrate 、 硼酸 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 0.67h， 以94%的产率得到(4s,6s)-6-Benzyloxymethyl-4-methyltetrahydro-2h-pyran-2-one
  参考文献：
  名称：

  Methyl 3-bromomethyl-3-butenoate as an isopentane building block for the stereoselective preparation of (S)-4-methyl-3,6-dihydro-2H-pyran-2-carbaldehyde and (+)-faranal

  摘要：

  (S)-4-Methyl-3,6-dihydro-2H-pyran-2-carbaldehyde (3), the common intermediate in the syntheses of the C17-C27 subunit of laulimalide (4) and (+)-faranal (5), the trail pheromone of the pharaoh ant, Monomorium pharaonis, were obtained via transformation of methyl 3-bromomethyl-3-butenoate (1) into allylstannane 2 and subsequent allylation of (benzyloxy)acetaldehyde (6) in accordance with the Keck procedure as the key steps. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.01.120
• 作为产物：
  描述：

  methyl 3-[(tributylstannyl)methyl]but-3-enoate 、 苄氧基乙醛 在 (R)-BITIP 作用下， 以 甲苯 为溶剂， 以85%的产率得到(R)-6-Benzyloxymethyl-4-methyl-5,6-
  参考文献：
  名称：

  氧化腈环加成反应中的 α,β-不饱和 β-甲基-δ-内酯。饱和内酯和内酰胺的合成

  摘要：

  摘要 通过将氧化乙腈环加成到 α,β-不饱和 β-甲基-δ-内酯上，以高收率合成了新的异恶唑啉衍生物。这些不饱和内酯已被用于获得β-甲基支链饱和内酯和内酰胺，以及具有反相羟基构型的内酯，遵循发散的方法。

  DOI：

  10.1134/s1070428022060033

文献信息

• Cyclopropane intermediates in the synthesis of chiral alcohols with methyl-branched carbon skeleton. Application in the synthesis of insect pheromones
  作者：V. N. Kovalenko、I. V. Mineeva

  DOI：10.1134/s1070428014070033

  日期：2014.7
• Methyl 3-bromomethyl-3-butenoate as an isopentane building block for the stereoselective preparation of (S)-4-methyl-3,6-dihydro-2H-pyran-2-carbaldehyde and (+)-faranal
  作者：Iryna V. Mineyeva、Oleg G. Kulinkovich

  DOI：10.1016/j.tetlet.2010.01.120

  日期：2010.4

  (S)-4-Methyl-3,6-dihydro-2H-pyran-2-carbaldehyde (3), the common intermediate in the syntheses of the C17-C27 subunit of laulimalide (4) and (+)-faranal (5), the trail pheromone of the pharaoh ant, Monomorium pharaonis, were obtained via transformation of methyl 3-bromomethyl-3-butenoate (1) into allylstannane 2 and subsequent allylation of (benzyloxy)acetaldehyde (6) in accordance with the Keck procedure as the key steps. (C) 2010 Elsevier Ltd. All rights reserved.
• α,β-Unsaturated β-Methyl-δ-lactones in Nitrile Oxide Cycloaddition Reactions. Synthesis of Saturated Lactones and Lactams
  作者：I. V. Mineyeva

  DOI：10.1134/s1070428022060033

  日期：2022.6

  Abstract New isoxazoline derivatives have been synthesized in high yields by cycloaddition of acetonitrile oxide to α,β-unsaturated β-methyl-δ-lactones. These unsaturated lactones have been used to obtain β-methyl branched saturated lactones and lactams, as well as lactones with an inversed configuration of hydroxy group, following the divergent approach.

  摘要 通过将氧化乙腈环加成到 α,β-不饱和 β-甲基-δ-内酯上，以高收率合成了新的异恶唑啉衍生物。这些不饱和内酯已被用于获得β-甲基支链饱和内酯和内酰胺，以及具有反相羟基构型的内酯，遵循发散的方法。