<<(phenylmethoxy)methoxy>methyl>oxirane | 76719-90-9

• 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: <<(phenylmethoxy)methoxy>methyl>oxirane
• 英文别名: [[(phenylmethoxy)methoxy]methyl]oxirane；glycidylbenzyloxymethylether；Oxirane, [[(phenylmethoxy)methoxy]methyl]-；2-(phenylmethoxymethoxymethyl)oxirane
• CAS: 76719-90-9
• 化学式: C₁₁H₁₄O₃
• 分子量: 194.23
• InChiKey: QVQGAZFPIYIYMB-UHFFFAOYSA-N

物化性质

• 沸点：
  281.0±20.0 °C(Predicted)
• 密度：
  1.130±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  14
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  31
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  <<(phenylmethoxy)methoxy>methyl>oxirane 在 氨 作用下， 以 乙醇 为溶剂， 反应 72.0h， 以2.76 g的产率得到3-(benzyloxy)methoxy-2-hydroxypropylamine
  参考文献：
  名称：

  Peptidyl and azapeptidyl methylketones as substrate analog inhibitors of papain and cathepsin B

  摘要：

  Peptidyl methylketones containing Phe, Tyr, Tyr(I) Tyr(I-2), Leu and Ile in P-2 were synthesized and tested as substrate analog reversible inhibitors of papain and bovine spleen cathepsin B. The most effective cathepsin B inhibitor contained Tyr(I-2) and displayed an inhibition constant of 4.7 mu M at pH 6.8 and 25 degrees C, while Leu or lie gave practically inert analogs. Replacement of the amino acids in P-2 with the analogous alpha-azaamino acids, as well as the glycine in P-1 with alpha-azaglycine, led to complete loss of inhibiting activity. Introducing alkoxy substituents at the methyl adjacent to the ketone group generally resulted in more effective inhibitors, with inhibition constants in the micromolar range for both papain and cathepsin B.

  DOI：

  10.1016/0223-5234(96)88312-7
• 作为产物：
  描述：

  苄基氯甲基醚 、 缩水甘油 在 N,N-二异丙基乙胺 作用下， 以 氯仿 为溶剂， 以56%的产率得到<<(phenylmethoxy)methoxy>methyl>oxirane
  参考文献：
  名称：

  Peptidyl and azapeptidyl methylketones as substrate analog inhibitors of papain and cathepsin B

  摘要：

  Peptidyl methylketones containing Phe, Tyr, Tyr(I) Tyr(I-2), Leu and Ile in P-2 were synthesized and tested as substrate analog reversible inhibitors of papain and bovine spleen cathepsin B. The most effective cathepsin B inhibitor contained Tyr(I-2) and displayed an inhibition constant of 4.7 mu M at pH 6.8 and 25 degrees C, while Leu or lie gave practically inert analogs. Replacement of the amino acids in P-2 with the analogous alpha-azaamino acids, as well as the glycine in P-1 with alpha-azaglycine, led to complete loss of inhibiting activity. Introducing alkoxy substituents at the methyl adjacent to the ketone group generally resulted in more effective inhibitors, with inhibition constants in the micromolar range for both papain and cathepsin B.

  DOI：

  10.1016/0223-5234(96)88312-7

文献信息

• Regioselective conversion of O-protected glycidols to fluorohydrins catalyuzed by tetrabutylammonium dihydrogentrifluoride under solid-liquid PTC conditions
  作者：Dario Landini、Domenico Albanese、Michele Penso

  DOI：10.1016/s0040-4020(01)92194-5

  日期：1992.1

  converted into the corresponding fluorohydrins FCH2CH(OH)CH2OX by reaction with catalytic amounts of Bu4N+H2F3- and a molar excess of KHF2. Most of the protective groups (X) examined are stable under the above conditions, moreover stereogenic carbons are not affected.

  许多ø -保护的缩水甘油被区域选择性地转化成相应的fluorohydrins FCH 2 CH（OH）CH 2用的卜催化量的反应OX 4 Ñ + ħ 2 ˚F 3 -和摩尔过量的KHF 2。所检查的大多数保护基（X）在上述条件下都是稳定的，而且立体碳不受影响。
• Regioselective opening of epoxides to β-amido alcohols under solid-liquid PTC conditions
  作者：Domenico Albanese、Dario Landini、Michele Penso

  DOI：10.1016/s0040-4020(97)00162-2

  日期：1997.3

  A study on the ring opening of a number of epoxides 1 with trifluoroacetamide (2) under solid-liquid phase transfer catalysis (SL-PTC) conditions has been performed. The reaction is completely regioselective affording β-amido alcohols 3 deriving from the attack of the nucleophile to the less substituted carbon atom of the oxirane ring.

  在固液相转移催化（SL-PTC）条件下，已进行了许多环氧化物1与三氟乙酰胺（2）的开环研究。该反应是完全区域选择性的，得到β-氨基醇3，其衍生自亲核体对环氧乙烷环的较少取代的碳原子的攻击。
• Peptidyl and azapeptidyl methylketones as substrate analog inhibitors of papain and cathepsin B
  作者：R Calabretta、C Giordano、C Gallina、V Morea、V Consalvi、R Scandurra

  DOI：10.1016/0223-5234(96)88312-7

  日期：1995.1

  Peptidyl methylketones containing Phe, Tyr, Tyr(I) Tyr(I-2), Leu and Ile in P-2 were synthesized and tested as substrate analog reversible inhibitors of papain and bovine spleen cathepsin B. The most effective cathepsin B inhibitor contained Tyr(I-2) and displayed an inhibition constant of 4.7 mu M at pH 6.8 and 25 degrees C, while Leu or lie gave practically inert analogs. Replacement of the amino acids in P-2 with the analogous alpha-azaamino acids, as well as the glycine in P-1 with alpha-azaglycine, led to complete loss of inhibiting activity. Introducing alkoxy substituents at the methyl adjacent to the ketone group generally resulted in more effective inhibitors, with inhibition constants in the micromolar range for both papain and cathepsin B.