(+/-)-3-methyl-1,4-pentanediol

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (+/-)-3-methyl-1,4-pentanediol
• 英文别名: 3-methylpentane-1,4-diol；(3R,4S)-3-methylpentane-1,4-diol
• 化学式: C₆H₁₄O₂
• 分子量: 118.176
• InChiKey: WOHXXIWTEHLCQK-RITPCOANSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  8
• 可旋转键数：
  3
• 环数：
  0.0
• 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：

  (+/-)-3-methyl-1,4-pentanediol 在 NaOH buffer 、 horse liver alcohol dehydrogenase 、 β-烟酰胺腺嘌呤二核苷酸 、 聚甘氨酸 作用下， 反应 3.0h， 生成 (3R,4S)-3,4-dimethylbutyrolactone
  参考文献：
  名称：

  Synthesis of diastereo- and enantiomerically pure anti-3-methyl-1,4-pentanediol via lipase catalysed acylation

  摘要：

  Racemic trans-4,5-dimethylhydrofuran-2(3H)-one was synthesised from 5-methyl-furan-2(3H)-one, (alpha-angelica lactone). The key reaction in the synthesis was the 1,4-conjugate addition of an organocuprate to 5-methylfuran-2(5H)-one (beta-angelica lactone). Different types of organocuprates were tested with the highest anti:syn ratio of 99.4:0.6 being obtained by the use of a Gilman organocuprate reagent. The enantioselective acylation of racemic 3-methyl-pentan-1,4-diol, catalysed by a variety of lipases in organic media, was investigated. The highest enantioselectivity (E > 400) was obtained when Novozyme 435 was used as the catalyst at a water activity of a(w) similar to 0. Thus, both enantiomers, (3S,4R)- and (3R,4S)-3-methyl-pentan-1,4-diol, were obtained in very high diastereomeric (> 99% de) and enantiomeric purities (> 99.8% and > 97.4% ee, respectively). (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.01.043
• 作为产物：
  描述：

  (3S,4R)-4-[hydroxy(dimethyl)silyl]-3-methylpentan-1-ol 在 potassium fluoride 、 双氧水 、 potassium hydrogencarbonate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 16.0h， 生成 (+/-)-3-methyl-1,4-pentanediol
  参考文献：
  名称：

  Early Transition Metal Induced Intramolecular Cocyclisation/Elaboration Reactions Using a Cleavable Silicon Linker

  摘要：

  含有硅氧键或硅氮键的 1,6- 和 1,7- 二烯和烯炔与锆碳（1-丁烯）或二异丙氧基钛（丙烯）共循环，生成金属双环。进一步加工后，使用 Tamao 氧化法裂解硅碳键，可得到多种有机产品。

  DOI：

  10.1055/s-1997-1059

文献信息

• Stereoselective synthesis of alicyclic ketones: A hydrogen borrowing approach
  作者：Roly J. Armstrong、Wasim M. Akhtar、James R. Frost、Kirsten E. Christensen、Neil G. Stevenson、Timothy J. Donohoe

  DOI：10.1016/j.tet.2019.130680

  日期：2019.11

  A highly diastereoselective annulation strategy for the synthesis of alicyclic ketones from diols and pentamethylacetophenone is described. This process is mediated by a commercially available iridium(III) catalyst, and provides efficient access to a wide range of cyclopentane and cyclohexane products with high levels of stereoselectivity. The origins of diastereoselectivity in the annulation reaction

  描述了一种由二醇和五甲基苯乙酮合成脂环族酮的高度非对映选择性环化策略。该方法由可商购的铱（III）催化剂介导，可有效地获得各种具有高立体选择性的环戊烷和环己烷产品。通过一系列控制实验探索了环空反应中非对映选择性的起源，这为如何控制新锻造环周围的每个立体中心提供了解释。
• Lactols in stereoselection 3
  作者：Katsuhiko Tomooka、Tatsuyuki Okinaga、Keisuke Suzuki、Gen-ichi Tsuchihashi

  DOI：10.1016/s0040-4039(00)99520-0

  日期：1989.1

  addition of MeTi(O-iPr)3 to α-chiral lactols proceeds in highly diastereoselective manner. The sense of the diastereofacial selection is anti-Cram-type, which provides a new and useful method for 1,2-asymmetric induction.

  MeTi（O-iPr）3的亲核加成反应以高度非对映选择性的方式进行。非对面选择的意义是反克拉姆式的，这为1，2-不对称诱导提供了一种新的有用的方法。
• Picolinamides with fungicidal activity
  申请人：DOW AGROSCIENCES LLC

  公开号：US10173971B2

  公开（公告）日：2019-01-08

  The invention relates to picolinamides of Formula I and their use as fungicides.

  本发明涉及式 I 的吡啶酰胺及其作为杀菌剂的用途。
• TOMOOKA, KATSUHIKO;OKINAGA, TATSUYUKI;SUZUKI, KEISUKE;TSUCHIHASHI, GEN-IC+, TETRAHEDRON LETT., 30,(1989) N2, C. 1563-1566
  作者：TOMOOKA, KATSUHIKO、OKINAGA, TATSUYUKI、SUZUKI, KEISUKE、TSUCHIHASHI, GEN-IC+

  DOI：——

  日期：——
• PICOLINAMIDES WITH FUNGICIDAL ACTIVITY
  申请人：DOW AGROSCIENCES LLC

  公开号：US20180037541A1

  公开（公告）日：2018-02-08

  The invention relates to picolinamides of Formula I and their use as fungicides.