(2R,5S)-2-(1-hydroxy-1-methylethyl)-5-methyltetrahydrofuran | 105814-94-6

• 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: (2R,5S)-2-(1-hydroxy-1-methylethyl)-5-methyltetrahydrofuran
• 英文别名: (2R,5S)-(+)-pityol；(+)-trans-Pityol；(2R,5S)-pityol；(E)-(+)-Pityol；Pityol；2-[(2R,5S)-5-methyloxolan-2-yl]propan-2-ol
• CAS: 105814-94-6
• 化学式: C₈H₁₆O₂
• 分子量: 144.214
• InChiKey: GDFJZYRQAYBNLM-NKWVEPMBSA-N

物化性质

• 沸点：
  195.6±8.0 °C(Predicted)
• 密度：
  0.981±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  10
• 可旋转键数：
  1
• 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

• 作为产物：
  描述：

  (S)-6-methyl-5-hepten-2-yl acetate 在 四溴化碳 、 Rhodococcus ruber DSM 44540 、 Tris buffer 、 potassium carbonate 、 间氯过氧苯甲酸 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 反应 101.5h， 生成 (2R,5S)-2-(1-hydroxy-1-methylethyl)-5-methyltetrahydrofuran
  参考文献：
  名称：

  Enantio- and diastereo-convergent synthesis of (2R,5R)- and (2R,5S)-Pityol through enzyme-triggered ring closure

  摘要：

  A short chemoenzymatic synthesis of the (2R,5S)- and (2R,5R)-stereoisomer of the bark beetle pheromone Pityol 1 was achieved from (+/-)-Sulcatol 2 in an enantio- and diastereo-convergent fashion without the formation of any 'unwanted' stereoisomer. The key steps include: (i) lipase-catalyzed deracemization of (+/-)-2 using kinetic resolution coupled to an in-situ inversion or alternatively, dynamic resolution using combined lipase- and Ru-catalysis: and (ii) creation of the second stereogenic center by an epoxide hydrolase-catalyzed diastereo-convergent hydrolysis of a haloalkyl oxirane, followed by spontaneous ring Closure to form 1 in a stereoselective fashion. (C) 2001 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(01)00370-6

文献信息

• Synthesis of optically pure pityol - a pheromone of the bark beetle Pityophthorus pityographus - using a chemoenzymatic route.
  作者：A. Archelas、R. Furstoss

  DOI：10.1016/s0040-4039(00)79143-x

  日期：1992.9

  A four step synthesis of (2R,5S)-pityol. the pheromone of Pityophthorus pityographus, is described using in particular two highly stereoselective microbiologically mediated reactions.
• MORI, KEHNDZI, BIOSAJEHNSU TO INDASUTORI, 46,(1988) N, S. 3262-3268
  作者：MORI, KEHNDZI

  DOI：——

  日期：——
• MORI, KENJI;PUAPOOMCHAREON, PRAPAI, LIEBIGS ANN. CHEM.,(1989) N2, C. 1261-1262
  作者：MORI, KENJI、PUAPOOMCHAREON, PRAPAI

  DOI：——

  日期：——
• ISHIHARA, KAZUAKI;MORI, ATSUNORI;YAMAMOTO, HISASHI, TETRAHEDRON LETT., 28,(1987) N 52, 6613-6616
  作者：ISHIHARA, KAZUAKI、MORI, ATSUNORI、YAMAMOTO, HISASHI

  DOI：——

  日期：——
• Stereoselective formation of metabolites from 2-methyl-2-hepten-6-one by Botrytis cinerea
  作者：Elisabeth Schwab、Alexander Bernreuther、Prapai Puapoomchareon、Kenji Mori、Peter Schreier

  DOI：10.1016/s0957-4166(00)82172-2

  日期：1991.1

  Controlled conversion of 2-methyl-2-hepten-6-one (1) by Botrytis cinerea resulted in the formation of (S)-(+)-2-methyl-2-hepten-6-ol (sulcatol) (2) of 90% ee. In addition, (2R,5R)- (3a), (2S,5S)- (3a'), (2R,5S)- (3b) and (2S,5R)-2-(1-hydroxy-1-methylethyl)-5-methyltetrahydrofuran (3b'), (3S,6R)- (4a), (3R,6S)- (4a'), (3R,6R)- (4b) and (3S,6S)-tetrahydro-2,2,6-trimethyl-2H-pyran-3-ol (4b') as well as the diastereomeric dihydro-3-hydroxy-5-methyl-5-(2'-methyl-pent-2-en-5'-yl)-2(3H)-furanones (5a/b) were found as biotransformations product of 1. Chiral analysis carried out by online multidimensional gas chromatography-mass spectrometry (MDGC-MS) revealed the following ee values: 46 % (3a); 80 % (3b); 56 % (4a); and 60 % (4b'). As confirmed by nOe experiments, 5a/b were formed in a ratio of 6:1.