S-6-Benzyloxyethyl-γ-butyrolactone | 108380-28-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: S-6-Benzyloxyethyl-γ-butyrolactone
• 英文别名: (S)-5-(2-(benzyloxy)ethyl)dihydrofuran-2(3H)-one；(5S)-5-(2-phenylmethoxyethyl)oxolan-2-one
• CAS: 108380-28-5
• 化学式: C₁₃H₁₆O₃
• 分子量: 220.268
• InChiKey: QIKIUVIXNHCHES-LBPRGKRZSA-N

物化性质

• 沸点：
  365.7±15.0 °C(Predicted)
• 密度：
  1.115±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  S-6-Benzyloxyethyl-γ-butyrolactone 在 palladium on activated charcoal 吡啶 、 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile 、 氢气 、 三正丁基氢锡 、 sodium iodide 作用下， 以 乙醇 、 丙酮 、 苯 为溶剂， 25.0 ℃ 、101.33 kPa 条件下， 反应 28.5h， 生成 4-hexanolide
  参考文献：
  名称：

  Gurjar, Mukund K.; Patil, Vijay J., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1986, vol. 25, p. 596 - 599

  摘要：

  DOI：
• 作为产物：
  描述：

  3-deoxy-1,2;5,6-di-O-isopropylidene-α-D-glucofuranoside 在 吡啶 、 盐酸 、 硫酸 、 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile 、 三氟化硼乙醚 、 双氧水 、 三正丁基氢锡 、 sodium acetate 、 sodium hydride 、 间氯过氧苯甲酸 、 sodium iodide 、 diborane(6) 作用下， 以 甲醇 、 二氯甲烷 、 甲苯 、 丁酮 为溶剂， 反应 49.5h， 生成 S-6-Benzyloxyethyl-γ-butyrolactone
  参考文献：
  名称：

  Gurjar, Mukund K.; Patil, Vijay J., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1986, vol. 25, p. 596 - 599

  摘要：

  DOI：

文献信息

• Carboxyl Group-Directed Iridium-Catalyzed Enantioselective Hydrogenation of Aliphatic γ-Ketoacids
  作者：Mao-Lin Li、Yao Li、Jia-Bin Pan、Yi-Hao Li、Song Song、Shou-Fei Zhu、Qi-Lin Zhou

  DOI：10.1021/acscatal.0c02142

  日期：2020.9.4

  occurrence of chiral induction involving a hydrogen–hydrogen interaction between a hydride on the iridium atom and the substituent on the oxazoline ring of the ligand, and on the basis of the calculations, we proposed a catalytic cycle involving only Ir(III), which differs from the Ir(III)/Ir(V) catalytic cycle that operates in the hydrogenation of α,β-unsaturated carboxylic acids.

  尽管已经广泛地研究了过渡金属催化的芳族酮的不对称氢化，但是脂肪族酮的对映选择性氢化仍然是一个挑战，因为手性催化剂不能轻易地区分这些酮的正反面。在这里，我们报道了脂肪族γ-酮酸不对称氢化的羧基导向策略。在具有手性螺膦-恶唑啉配体的铱配合物的催化下，脂肪族γ-酮酸的氢化得到具有高对映选择性（高达99％ee）的手性γ-羟基内酯。机理研究表明，底物的羧基指导氢转移并确保高对映选择性。
• Iridium-Catalyzed C–C Coupling of a Simple Propargyl Ether with Primary Alcohols: Enantioselective Homoaldol Addition via Redox-Triggered (<i>Z</i>)-Siloxyallylation
  作者：Tao Liang、Wandi Zhang、Michael J. Krische

  DOI：10.1021/jacs.5b12131

  日期：2015.12.30

  A chiral iridium complex formed in situ from [Ir(cod)Cl](2) and (R)-H-8-BINAP is found to catalyze the direct enantioselective C C coupling of a simple propargyl ether, TIPSOCH2C CH, with primary alcohols to form gamma-hydroxy (Z)-enol silanes with uniformly high enantioselectivity and complete alkene (Z)-stereo-selectivity. As corroborated by deuterium labeling studies, these studies represent the first examples of 1,2-hydride shift-enabled pi-allyl formation in the context of iridium catalysis.
• A Direct Method for the Conversion of Terminal Epoxides into γ-Butanolides
  作者：Mohammad Movassaghi、Eric N. Jacobsen

  DOI：10.1021/ja025604c

  日期：2002.3.1

  A new and efficient process for the conversion of terminal epoxides to gamma-butanolides is described involving Lewis acid promoted epoxide ring-opening by 1-morpholino-2-trimethylsilyl acetylene. Addition of a terminal epoxide to a solution of the ynamine and boron trifluoride diethyl etherate in dichloromethane at 0 degrees C rapidly affords a cyclic keteneaminal that can be hydrolyzed and protodesilylated under mild conditions to provide the corresponding gamma-butanolide in high yield. The net transformation is equivalent to an acetate enolate opening of terminal epoxides. The formation of a cyclic keteneaminal as the direct addition product was observed by monitoring of the reaction by IR and NMR spectroscopy. Functionalized gamma-lactones were prepared by the interception of the reactive cyclic keteneaminal prior to hydrolysis. Reactions with enantiomerically enriched terminal epoxides provide the corresponding gamma-butanolides without loss of optical activity. The compatibility of the present methodology with a wide range of functional groups is noteworthy.