(1S)-1-[(2S)-oxolan-2-yl]propan-1-ol | 24482-78-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧唑烯
• 英文名称: (1S)-1-[(2S)-oxolan-2-yl]propan-1-ol
• CAS: 24482-78-8；33964-62-4；110243-79-3；149818-46-2；149818-47-3；33964-64-6
• 化学式: C₇H₁₄O₂
• 分子量: 130.187
• InChiKey: YURZFYINXLRBDR-BQBZGAKWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  9
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1S)-1-[(2S)-oxolan-2-yl]propan-1-ol 在 三甲基氯硅烷 、 无水碳酸镉 、 sodium iodide 、 mercury dichloride 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 6.0h， 生成 (4'S,5'S)-5-(5-Ethyl-2,2-dimethyldioxolan-4-yl)pentan-2-one
  参考文献：
  名称：

  Dihyro- and tetrahydrofuran building blocks from 1,4:3,6-dianhydromannitol. 1. Synthesis of (1S,5R,7R)-endo-(-)- and (1S,5R,7S)-(-)-exo-brevicomin and (R)-(+)-dodecanolide

  摘要：

  The eliminative ring fission of iodides derived from 1,4:3,6-dianhydromannitol3 has been exploited for preparing three enantiomerically pure species, 1-3, which feature a di-or tetrahydrofuran moiety and one or two stereogenic centers. These species are extremely versatile building blocks for the construction of natural products. Their potential was demonstrated by the synthesis of the title insect pheromones.

  DOI：

  10.1021/jo00069a015
• 作为产物：
  描述：

  (2S,1'S)-(-)-2-(1-Hydroxypropyl)-2,5-dihydrofuran 在 palladium on activated charcoal 氢气 作用下， 以 乙醚 为溶剂， 反应 4.0h， 生成 (1S)-1-[(2S)-oxolan-2-yl]propan-1-ol
  参考文献：
  名称：

  Dihyro- and tetrahydrofuran building blocks from 1,4:3,6-dianhydromannitol. 1. Synthesis of (1S,5R,7R)-endo-(-)- and (1S,5R,7S)-(-)-exo-brevicomin and (R)-(+)-dodecanolide

  摘要：

  The eliminative ring fission of iodides derived from 1,4:3,6-dianhydromannitol3 has been exploited for preparing three enantiomerically pure species, 1-3, which feature a di-or tetrahydrofuran moiety and one or two stereogenic centers. These species are extremely versatile building blocks for the construction of natural products. Their potential was demonstrated by the synthesis of the title insect pheromones.

  DOI：

  10.1021/jo00069a015

文献信息

• Chelation-controlled reduction of α- and β-oxygenated ketones with lithium tri-n-butylborohydride
  作者：Anne-Marie Faucher、Christian Brochu、Serge R. Landry、Isabelle Duchesne、Susanne Hantos、Amélie Roy、Andrew Myles、Claude Legault

  DOI：10.1016/s0040-4039(98)01883-8

  日期：1998.11

  Lithium tri-n-butyl borohydride showed high selectivity in the reduction of α- and β-oxygenated ketones, giving a preponderance of the chelation controlled products.

  锂三Ñ丁基硼氢化表现出较高的选择性，α-和β-含氧将酮还原，得到螯合控制产品占优势的。
• Oxidative cyclization of alkenols with Oxone using a miniflow reactor
  作者：Yoichi M A Yamada、Kaoru Torii、Yasuhiro Uozumi

  DOI：10.3762/bjoc.5.18

  日期：——

  A miniflow system for oxidative cyclization of alkenols with Oxone was developed. Thus, the oxidative cyclization of (Z)- and (E)-alkenols in i-PrOH with an aqueous solution of Oxone proceeded smoothly and safely in a PTFE tube without any exogenous catalytic species, and was subsequently quenched in a flow-reaction manner to afford the corresponding furanyl and pyranyl carbinols quantitatively within 5 or 10 min of residence time.

  开发了一种使用Oxone进行烯醇氧化环化的小流量系统。因此，(Z)-和(E)-烯醇在-PrOH中与Oxone的水溶液在PTFE管中顺利、安全地进行氧化环化，无需任何外源催化物，并随后以流动反应方式迅速熄灭，在5或10分钟的停留时间内定量地得到相应的呋喃基和吡喃基羟基化合物。
• Tightly Convoluted Polymeric Phosphotungstate Catalyst:  An Oxidative Cyclization of Alkenols and Alkenoic Acids
  作者：Yoichi M. A. Yamada、Haiqing Guo、Yasuhiro Uozumi

  DOI：10.1021/ol070258v

  日期：2007.4.1

  A tightly convoluted polymeric phosphotungstate catalyst was prepared via ionic assembly of H3PW12O40 and poly(alkylpyridinium). An oxidative cyclization of various alkenols and alkenoic acids was efficiently promoted by the polymeric catalyst in aq H2O2 in the absence of organic solvents to afford the corresponding cyclic ethers and lactones in high yield. The catalyst was reused four times without loss of catalytic activity.
• Diastereoselectivite dans la reaction des organomagnesiens sur le tetrahydrofurfural et son gem-diacetate en presence de HMPT. Acces aux diols-1,2 erythro
  作者：R. Amouroux、S. Ejjiyar、M. Chastrette

  DOI：10.1016/s0040-4039(86)80041-7

  日期：1986.1
• Dihyro- and tetrahydrofuran building blocks from 1,4:3,6-dianhydromannitol. 1. Synthesis of (1S,5R,7R)-endo-(-)- and (1S,5R,7S)-(-)-exo-brevicomin and (R)-(+)-dodecanolide
  作者：Vanda Cere、Claudio Mazzini、Claudio Paolucci、Salvatore Pollicino、Antonino Fava

  DOI：10.1021/jo00069a015

  日期：1993.8

  The eliminative ring fission of iodides derived from 1,4:3,6-dianhydromannitol3 has been exploited for preparing three enantiomerically pure species, 1-3, which feature a di-or tetrahydrofuran moiety and one or two stereogenic centers. These species are extremely versatile building blocks for the construction of natural products. Their potential was demonstrated by the synthesis of the title insect pheromones.