2-(4,5-Dihydroxy-4-methylpentyl)-2-methyl-1,3-dioxolane | 83953-56-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 2-(4,5-Dihydroxy-4-methylpentyl)-2-methyl-1,3-dioxolane
• 英文别名: 2-Methyl-5-(2-methyl-1,3-dioxolan-2-yl)pentane-1,2-diol
• CAS: 83953-56-4
• 化学式: C₁₀H₂₀O₄
• 分子量: 204.266
• InChiKey: FCBLGSMNZOFCHR-UHFFFAOYSA-N

物化性质

• 沸点：
  160-162 °C(Press: 14 Torr)
• 密度：
  1.087±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  58.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(4,5-Dihydroxy-4-methylpentyl)-2-methyl-1,3-dioxolane 在 对甲苯磺酸 作用下， 生成 (1S,5R)-1,5-二甲基-6,8-二氧杂双环[3.2.1]辛烷
  参考文献：
  名称：

  有机金属碲化物作为有机金属的来源：在合成（+/-）-额叶蛋白中的应用

  摘要：

  通过碲/锂交换产生的被掩盖的均烯酸锂与环氧化物反应。锂化合物也被转化为其他有机金属，例如格利雅（Grignard），并评估了铜酸盐和这些有机金属与环氧化物的反应性。在（+/-）-额叶蛋白的合成中使用了相同的结构单元。

  DOI：

  10.1016/j.tetlet.2006.10.039
• 作为产物：
  描述：

  2-Methoxy-1,4-pentadien 在 四氧化锇 、 十二/十四烷基二甲基氧化胺 、 对甲苯磺酸 作用下， 以 水 、 甲苯 、 叔丁醇 为溶剂， 反应 11.0h， 生成 2-(4,5-Dihydroxy-4-methylpentyl)-2-methyl-1,3-dioxolane
  参考文献：
  名称：

  Nonracemic frontalin via copper- and palladium-based skeletal construction and the asymmetric dihydroxylation

  摘要：

  The new higher order organocuprate, Li2Cu(CN)(C(OMe):CH2)2, prepared through a Sn --> Li --> Cu transmetalation sequence, was found to efficiently couple with allyl bromide producing 2-methoxy-1,4-pentadiene (3) which is efficiently converted to the ketal 4. Hydroboration of 4 with 9-BBN-H and the selective oxidation of this adduct with trimethylamine N-oxide (TMANO) produces 9-oxa-10-borabicyclo[3.3.2]decane 5, which undergoes Pd-catalyzed cross coupling with 2-bromopropene producing 6, thereby accomplishing the construction of the frontalin carbon skeleton in 63% overall yield from allyl bromide. The Os-based dihydroxylation of 6 followed by ketalization either produces the racemic pheromone ((+/-)-1) or, with the Sharpless catalytic asymmetric dihydroxylation (dihydroquinine ligand) procedure, results in the selective formation of the S enantiomer in 35% ee. The de determined from the C-13 NMR spectra of the diastereomeric Mosher's monoesters (9) was found to provide useful corroborative information on the optical purity of the intermediate 1,2-diols 7.

  DOI：

  10.1021/jo00048a014

文献信息

• Enantioselective Syntheses of (+)- and (−)-Frontalin
  作者：Masaki Ohwa、Ernest L. Eliel

  DOI：10.1246/cl.1987.41

  日期：1987.1.5

  (+)- and (−)-Frontalin have been obtained from a chiral 1,3-oxathiane precursor in a short (3-step) synthesis in moderate (70%) enantiomeric excess (e.e.). A longer (6-step) modification gives the ...

  (+)- 和 (-)-Frontalin 是从手性 1,3-氧杂环丙烷前体以中等 (70%) 对映体过量 (ee) 的短（3 步）合成获得的。更长的（6 步）修改使...
• MYRSINA, R. A.;KUZNETSOV, N. V.;MAKARENKO, V. E., YKP. XIM. ZH., 1982, 48, N 9, 991-993
  作者：MYRSINA, R. A.、KUZNETSOV, N. V.、MAKARENKO, V. E.

  DOI：——

  日期：——
• Nonracemic frontalin via copper- and palladium-based skeletal construction and the asymmetric dihydroxylation
  作者：Braulio Santiago、John A. Soderquist

  DOI：10.1021/jo00048a014

  日期：1992.10

  The new higher order organocuprate, Li2Cu(CN)(C(OMe):CH2)2, prepared through a Sn --> Li --> Cu transmetalation sequence, was found to efficiently couple with allyl bromide producing 2-methoxy-1,4-pentadiene (3) which is efficiently converted to the ketal 4. Hydroboration of 4 with 9-BBN-H and the selective oxidation of this adduct with trimethylamine N-oxide (TMANO) produces 9-oxa-10-borabicyclo[3.3.2]decane 5, which undergoes Pd-catalyzed cross coupling with 2-bromopropene producing 6, thereby accomplishing the construction of the frontalin carbon skeleton in 63% overall yield from allyl bromide. The Os-based dihydroxylation of 6 followed by ketalization either produces the racemic pheromone ((+/-)-1) or, with the Sharpless catalytic asymmetric dihydroxylation (dihydroquinine ligand) procedure, results in the selective formation of the S enantiomer in 35% ee. The de determined from the C-13 NMR spectra of the diastereomeric Mosher's monoesters (9) was found to provide useful corroborative information on the optical purity of the intermediate 1,2-diols 7.
• Organotellurides as a source of organometallics: application in the synthesis of (+/−)-frontalin
  作者：Alcindo A. Dos Santos、Renan S. Ferrarini、Jefferson L. Princival、João V. Comasseto

  DOI：10.1016/j.tetlet.2006.10.039

  日期：2006.12

  A masked lithium homoenolate, generated by tellurium/lithium exchange, was reacted with epoxides. The lithium compound was also converted into other organometallics such as Grignard, and cuprates and the reactivity of those organometallics with epoxides was evaluated. The same building block was employed in the synthesis of (+/−)-frontalin.

  通过碲/锂交换产生的被掩盖的均烯酸锂与环氧化物反应。锂化合物也被转化为其他有机金属，例如格利雅（Grignard），并评估了铜酸盐和这些有机金属与环氧化物的反应性。在（+/-）-额叶蛋白的合成中使用了相同的结构单元。