(2RS,3SR)-2-methyl-3-phenyloxiranecarboxamide

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 环氧化物
• 英文名称: (2RS,3SR)-2-methyl-3-phenyloxiranecarboxamide
• 英文别名: (2RS,3SR)-2,3-epoxy-2-methyl-3-phenyl-propionic acid amide；(2RS,3SR)-2,3-Epoxy-2-methyl-3-phenyl-propionsaeure-amid；(2R,3S)-2-methyl-3-phenyloxirane-2-carboxamide
• 化学式: C₁₀H₁₁NO₂
• 分子量: 177.203
• InChiKey: FAGCPNFBSVVXEK-WCBMZHEXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  55.6
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2RS,3SR)-2-methyl-3-phenyloxiranecarboxamide 在 sodium azide 、 magnesium sulfate 、 对甲苯磺酸 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 38.0h， 生成 (2S,3S)-2-Amino-3-hydroxy-2-methyl-3-phenyl-propionamide
  参考文献：
  名称：

  丁腈生物转化，用于高对映选择性合成具有叔和四级立体中心的环氧乙烷甲酰胺；对映纯α-甲基化丝氨酸和异丝氨酸衍生物的高效化学酶学方法

  摘要：

  使用Rhodococcus sp。进行许多不同取代和构型的环氧乙烷腈的生物转化。研究了含有腈水合酶/酰胺酶的微生物全细胞催化剂AJ270。虽然几乎所有的反式构型的3-芳基-2-甲基环氧乙烷腈和2,3-二甲基-3-苯基环氧乙烷腈都可以通过对映选择性较低的腈水合酶有效地水合，但酰胺酶对2-的表现出优异的2 S，3 R-对映选择性。甲基-3-（对位取代苯基）环氧乙烷甲酰胺。在非常温和的条件下，腈的生物转化提供了2 R，3 S的高效，实用合成-（-）-3-芳基-2-甲基环氧乙烷羧酰胺，具有叔和季立体中心的亲电环氧化物，收率极好，对映体过量大于99.5％。所得对映体纯环氧化合物的合成应用通过具有季立体中心的多官能化手性分子（如R -（+）-2-羟基-2-甲基-2-甲基-3-苯基丙酸，2 R和3 R）的方便，直接合成得到了证明。-（-）-3-氨基-2-羟基-2-甲基-3-苯基丙酸和2 S，3 S -（

  DOI：

  10.1021/jo0482615
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 ammonium hydroxide 作用下， 生成 (2RS,3SR)-2-methyl-3-phenyloxiranecarboxamide
  参考文献：
  名称：

  Posterior Lumbar Interbody Fusion

  摘要：

  Posterior lumbar interbody fusion has been practiced for more than 50 years. There is little question that interbody techniques offer a significantly higher fusion rate than traditional posterolateral techniques, but the morbidity associated with autograft harvest, the risks of root injury or dural tear during graft placement, and the high pseudarthrosis rate noted when allograft is substituted for autograft have conspired to minimize the widespread use of the procedure.Recently, various types of interbody cages have been developed in an effort to minimize autograft harvest requirements, reestablish disc and foraminal height, and decrease the risks of graft extrusion or collapse. Instrumentation developed for the placement of such cages has improved the surgeon's ability to perform complete discectomy, to properly prepare endplates, to reestablish lordosis, and to minimize the risk to the exiting nerve roots and dural canal.An experienced surgeon may expect fusion rates of 80% to 90% in one or two level lumbar fusions performed for degenerative disease using current techniques. Future improvements using more biocompatible or bioresorbable devices and various bone morphogenetic proteins will extend the life of these techniques well into the next century.

  DOI：

  10.1097/00127927-200106000-00006

文献信息

• Posterior Lumbar Interbody Fusion
  作者：Mark D. Oliver、David W. Cahill、Michael V. Hajjar

  DOI：10.1097/00127927-200106000-00006

  日期：2001.6

  Posterior lumbar interbody fusion has been practiced for more than 50 years. There is little question that interbody techniques offer a significantly higher fusion rate than traditional posterolateral techniques, but the morbidity associated with autograft harvest, the risks of root injury or dural tear during graft placement, and the high pseudarthrosis rate noted when allograft is substituted for autograft have conspired to minimize the widespread use of the procedure.Recently, various types of interbody cages have been developed in an effort to minimize autograft harvest requirements, reestablish disc and foraminal height, and decrease the risks of graft extrusion or collapse. Instrumentation developed for the placement of such cages has improved the surgeon's ability to perform complete discectomy, to properly prepare endplates, to reestablish lordosis, and to minimize the risk to the exiting nerve roots and dural canal.An experienced surgeon may expect fusion rates of 80% to 90% in one or two level lumbar fusions performed for degenerative disease using current techniques. Future improvements using more biocompatible or bioresorbable devices and various bone morphogenetic proteins will extend the life of these techniques well into the next century.
• Nitrile Biotransformations for Highly Enantioselective Synthesis of Oxiranecarboxamides with Tertiary and Quaternary Stereocenters; Efficient Chemoenzymatic Approaches to Enantiopure α-Methylated Serine and Isoserine Derivatives
  作者：Mei-Xiang Wang、Gang Deng、De-Xian Wang、Qi-Yu Zheng

  DOI：10.1021/jo0482615

  日期：2005.4.1

  2-methyl-3-(para-substituted-phenyl)oxiranecarboxamides. Under very mild conditions, biotransformations of nitriles provided an efficient and practical synthesis of 2R,3S-(−)-3-aryl-2-methyloxiranecarboxamides, electrophilic epoxides with tertiary and quaternary stereocenters, in excellent yield with enantiomeric excess greater than 99.5%. The synthetic applications of the resulting enantiomerically pure

  使用Rhodococcus sp。进行许多不同取代和构型的环氧乙烷腈的生物转化。研究了含有腈水合酶/酰胺酶的微生物全细胞催化剂AJ270。虽然几乎所有的反式构型的3-芳基-2-甲基环氧乙烷腈和2,3-二甲基-3-苯基环氧乙烷腈都可以通过对映选择性较低的腈水合酶有效地水合，但酰胺酶对2-的表现出优异的2 S，3 R-对映选择性。甲基-3-（对位取代苯基）环氧乙烷甲酰胺。在非常温和的条件下，腈的生物转化提供了2 R，3 S的高效，实用合成-（-）-3-芳基-2-甲基环氧乙烷羧酰胺，具有叔和季立体中心的亲电环氧化物，收率极好，对映体过量大于99.5％。所得对映体纯环氧化合物的合成应用通过具有季立体中心的多官能化手性分子（如R -（+）-2-羟基-2-甲基-2-甲基-3-苯基丙酸，2 R和3 R）的方便，直接合成得到了证明。-（-）-3-氨基-2-羟基-2-甲基-3-苯基丙酸和2 S，3 S -（