2-oxo-tetrahydro-2H-pyran-3-carboxylic acid tert-butyl ester | 153851-13-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: 2-oxo-tetrahydro-2H-pyran-3-carboxylic acid tert-butyl ester
• 英文别名: tert-butyl 3,4,5,6-tetrahydro-2-oxo-2H-pyran-3-carboxylate；tert-butyl tetrahydro-2-oxo-2H-pyran-3-carboxylate；α-tert-butoxycarbonylvalerolactone；Tert-butyl 2-oxooxane-3-carboxylate
• CAS: 153851-13-9
• 化学式: C₁₀H₁₆O₄
• 分子量: 200.235
• InChiKey: YHACLTLVEPFQPT-UHFFFAOYSA-N

物化性质

• 沸点：
  307.1±35.0 °C(Predicted)
• 密度：
  1.105±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-oxo-tetrahydro-2H-pyran-3-carboxylic acid tert-butyl ester 在 2,6-二甲基吡啶 、 (R)-DTBM-SEGPHOS palladium(II) 、 N-氟代双苯磺酰胺 作用下， 以 叔丁醇 为溶剂， 反应 27.0h， 生成 (S)-3-Fluoro-2-oxo-tetrahydro-pyran-3-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Enantioselective Fluorination of tert-Butoxycarbonyl Lactones and Lactams Catalyzed by Chiral Pd(II)-Bisphosphine Complexes

  摘要：

  An efficient catalytic enantioselective fluorination of tert-butoxycarbonyl lactones and lactams is reported. Reactions of the lactone substrates proceeded smoothly in an alcoholic solvent with a catalytic amount of chiral Pd(II) complex. In the case of the less acidic lactam substrates, concurrent use of the Pd complex and 2,6-lutidine as a cocatalyst was effective. Under the reaction conditions, the fluorinated lactones and lactams were obtained in good yield with excellent enantioselectivity (94-99% ee).

  DOI：

  10.1021/jo062048m
• 作为产物：
  描述：

  tert-butyl 3-iodopropyl propanedioate 在 四乙基溴化铵 、 sodium hydride 作用下， 以 苯 为溶剂， 反应 1.0h， 以70%的产率得到2-oxo-tetrahydro-2H-pyran-3-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Kobayashi, Kazuhiro; Minakawa, Hiroki; Sakurai, Hideo, Journal of the Chemical Society. Perkin transactions I, 1993, # 23, p. 3007 - 3010

  摘要：

  DOI：

文献信息

• Enantioselective Phase-Transfer Catalytic α-Benzylation and α-Allylation of α-<i>tert</i>-Butoxycarbonyllactones
  作者：Min Woo Ha、Heejin Lee、Hye Yeong Yi、Yohan Park、Sori Kim、Suckchang Hong、Myungmo Lee、Mi-hyun Kim、Taek-Soo Kim、Hyeung-geun Park

  DOI：10.1002/adsc.201200976

  日期：2013.3.11

  A new enantioselective α‐benzylation and α‐allylation of α‐tert‐butoxycarbonyllactones was devloped. α‐Benzylation and α‐allylation of α‐tert‐butoxycarbonylbutyrolactone and α‐tert‐butoxycarbonylvalerolactone under phase‐transfer catalytic conditions (50% cesium hydroxide, toluene, −60 °C) in the presence of (S,S)‐3,4,5‐trifluorophenyl‐NAS bromide (1 mol%) afforded the corresponding α‐substituted

  开发了新的对映选择性α-苄基化和α-叔丁氧基羰基内酯的α-烯丙基化。在（S，S）-3存在下，在相转移催化条件下（50％氢氧化铯，甲苯，-60°C），α-叔丁氧基羰基丁内酯和α-叔丁氧基羰基戊内酯的α-苄基化和α-烯丙基化， 4,5-三氟苯基-NAS溴化物（1 mol％）以非常高的化学收率（高达99％）和光学收率（高达ee的99％）提供了相应的α-取代的α-取代的α-叔丁氧基羰基内酯）。非天然α-季高丝氨酸，3-烷基-3-羧基吡咯烷和3-烷基-3-羧基哌啶的不对称合成已成功证明了该方法的合成潜力。
• Kobayashi, Kazuhiro; Minakawa, Hiroki; Sakurai, Hideo, Journal of the Chemical Society. Perkin transactions I, 1993, # 23, p. 3007 - 3010
  作者：Kobayashi, Kazuhiro、Minakawa, Hiroki、Sakurai, Hideo、Kujime, Sachiko、Suginome, Hiroshi

  DOI：——

  日期：——
• Enantioselective Fluorination of <i>tert</i>-Butoxycarbonyl Lactones and Lactams Catalyzed by Chiral Pd(II)-Bisphosphine Complexes
  作者：Toshiaki Suzuki、Tomomi Goto、Yoshitaka Hamashima、Mikiko Sodeoka

  DOI：10.1021/jo062048m

  日期：2007.1.1

  An efficient catalytic enantioselective fluorination of tert-butoxycarbonyl lactones and lactams is reported. Reactions of the lactone substrates proceeded smoothly in an alcoholic solvent with a catalytic amount of chiral Pd(II) complex. In the case of the less acidic lactam substrates, concurrent use of the Pd complex and 2,6-lutidine as a cocatalyst was effective. Under the reaction conditions, the fluorinated lactones and lactams were obtained in good yield with excellent enantioselectivity (94-99% ee).