(2R,5R)-(-)-pityol | 122517-46-8

• 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: (2R,5R)-(-)-pityol
• 英文别名: 2-[(2R,5R)-5-methyloxolan-2-yl]propan-2-ol
• CAS: 122517-46-8
• 化学式: C₈H₁₆O₂
• 分子量: 144.214
• InChiKey: GDFJZYRQAYBNLM-RNFRBKRXSA-N

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：

  6-甲基-5-庚烯-2-醇 在 Candida antarctica lipase B 、 四溴化碳 、 Rhodococcus ruber DSM 44540 、 Tris buffer 、 硫酸 、 potassium carbonate 、 间氯过氧苯甲酸 、 三苯基膦 作用下， 以 正庚烷 、 二氯甲烷 为溶剂， 反应 211.5h， 生成 (2R,5R)-(-)-pityol
  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

• Enzyme-triggered opening of an epoxide: Chemoenzymatic synthesis of (2R,5R)- and (2S,5R)-pityol
  作者：Martin Mischitz、Alexandra Hackinger、Iris Francesconi、Kurt Faber

  DOI：10.1016/s0040-4020(01)85340-0

  日期：1994.1

  Treatment of a diastereomeric mixture of (±)-epoxy-ester 1 with a crude immobilised enzyme preparation (Novo SP 409) or whole lyophilized cells of Rhodococcus erythropolis NCIB 11540 in aqueous buffer (pH 7.0) did not lead to the formation of the expected epoxy alcohol 2 or diol 5 but surprisingly furnished the rearranged products 4a and 4b in >98% enantiomeric excess. (2R*,5R*)-2-(1-Hydroxy- 1 -m

  用粗制的固定化酶制剂（Novo SP 409）或红球红球菌NCIB 11540的冻干全细胞在水性缓冲液（pH 7.0）中处理（±）-环氧酯1的非对映混合物环氧醇2或二醇5，但出人意料的是提供的重排产物4a和4b对映体过量> 98％。（2 R *，5 R *）-2-（1-羟基-1-甲基乙基）-5-甲基四氢呋喃（pityol，4a）是榆树皮甲虫Pteleobius vittatus的信息素。苯甲醇不是由环氧酒精形成的事实2 在没有生物催化剂的情况下，我们得出的结论是重排是由酶触发的。
• 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：——
• Mori, Kenji; Puapoomchareon, Prapai, Liebigs Annalen der Chemie, 1989, p. 1261 - 1262
  作者：Mori, Kenji、Puapoomchareon, Prapai

  DOI：——

  日期：——
• Enantio- and diastereo-convergent synthesis of (2R,5R)- and (2R,5S)-Pityol through enzyme-triggered ring closure
  作者：Andreas Steinreiber、Klaus Edegger、Sandra F. Mayer、Kurt Faber

  DOI：10.1016/s0957-4166(01)00370-6

  日期：2001.8

  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.