dl-erythro-ethyl 3-hydroxy-2-(phenylselenyl)butyrate | 99018-39-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 英文名称: dl-erythro-ethyl 3-hydroxy-2-(phenylselenyl)butyrate
• 英文别名: ethyl (2R,3R)-3-hydroxy-2-phenylselanylbutanoate
• CAS: 99018-39-0
• 化学式: C₁₂H₁₆O₃Se
• 分子量: 287.217
• InChiKey: NQQRWFIRWFJVGC-MWLCHTKSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.75
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  dl-erythro-ethyl 3-hydroxy-2-(phenylselenyl)butyrate 在 二异丁基氢化铝 作用下， 以 乙醚 、 甲苯 为溶剂， 反应 0.5h， 生成 (4β,5α)-(+/-)-4-methyl-5-(phenylselenyl)-1,3-dioxan-2-one
  参考文献：
  名称：

  Synthesis of 4-methyl- and 4,4-dimethyl-1,3-dioxin-2(4H)-one and related enol carboxylates

  摘要：

  DOI：

  10.1021/jo00225a069
• 作为产物：
  描述：

  二苯基二硒醚 、 ethyl (E)-2,3-epoxybutyrate 在 sodium tetrahydroborate 作用下， 生成 dl-erythro-ethyl 3-hydroxy-2-(phenylselenyl)butyrate
  参考文献：
  名称：

  Synthesis of 4-methyl- and 4,4-dimethyl-1,3-dioxin-2(4H)-one and related enol carboxylates

  摘要：

  DOI：

  10.1021/jo00225a069

文献信息

• Simple and efficient stereocontrol of radical allylations of β-hydroxy esters
  作者：Michèle Gerster、Laurent Audergon、Nadira Moufid、Philippe Renaud

  DOI：10.1016/0040-4039(96)01396-2

  日期：1996.8

  Highly stereoselective radical allylations of non-protected β-hydroxy esters have been achieved after formation of chelated aluminum alkoxides upon treatment with MeAlR2. This approach combines very high selectivities, excellent reproductibility and simplicity of the manipulations. Interestingly, diethyl malate is allylated after treatment with 1.1 equiv. of MAD to the threo (syn) isomer with almost

  在用MeAlR 2处理形成螯合的烷氧基铝之后，已经实现了未保护的β-羟基酯的高度立体选择性自由基烯丙基化。这种方法具有很高的选择性，出色的可重复性和操作简便性。有趣的是，苹果酸二乙酯在用1.1当量处理后被烯丙基化。MAD到的苏（顺式）异构体几乎完全非对映选择性（> 95个％DS），该立体化学结果是相反的在相应的烯醇化物的公知的烷基化中观察到的一个。
• Investigation of a model for 1,2-asymmetric induction in reactions of .alpha.-carbalkoxy radicals: a stereochemical comparison of reactions of .alpha.-carbalkoxy radicals and ester enolates
  作者：David J. Hart、Ramanarayanan Krishnamurthy

  DOI：10.1021/jo00042a029

  日期：1992.7

  The stereochemical course of reductions and allylations of alpha-carbalkoxy radicals with chiral centers at the beta-position are reported. Radicals without polar substituents, with alkoxyl or acetoxyl groups, and with hydroxyl groups at the beta-position were examined. Reactions showed selectivities ranging from low (50:50) to high (99:1). The results are discussed in terms of transition-state models that emphasize the importance of (1) allylic conformational analysis (minimization of A1,3 and A1,2 strain), (2) torisonal strain (minimization of eclipsed interactions), and (3) stereoelectronic effects.
• BUYNAK, J. D.;CHANDRASEKARAN, RAMALAKSHMI;BARRETT, A. G. M.;ATTRILL, R. P+, J. ORG. CHEM., 1985, 50, N 25, 5362-5365
  作者：BUYNAK, J. D.、CHANDRASEKARAN, RAMALAKSHMI、BARRETT, A. G. M.、ATTRILL, R. P+

  DOI：——

  日期：——