methyl β-hydroxy-α-phenylvalerate | 135366-65-3

• 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: methyl β-hydroxy-α-phenylvalerate
• 英文别名: Methyl 3-hydroxy-3-methyl-2-phenylbutanoate；methyl 3-hydroxy 3-methyl-2-phenylbutyrate；methyl 3-hydroxy-3-methyl-2-phenylbutyrate；Methyl I+/--(1-hydroxy-1-methylethyl)benzeneacetate
• CAS: 135366-65-3
• 化学式: C₁₂H₁₆O₃
• 分子量: 208.257
• InChiKey: DMWHLRQQZBRRPS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  15
• 可旋转键数：
  4
• 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：

  methyl β-hydroxy-α-phenylvalerate 、 氟磺酸 、 氯氟磺酰 生成 (1-methoxy-3-methyl-3-oxonio-2-phenylbutylidene)oxidanium
  参考文献：
  名称：

  BERNER D.; DAHN H.; VOGEL P., HELV. CHIM. ACTA, 1980, 63, NO 8, 2538-2553

  摘要：

  DOI：
• 作为产物：
  描述：

  苯乙酸甲酯 在 sodium hexamethyldisilazane 、 二甲基二环氧乙烷 作用下， 生成 DL-扁桃酸甲酯 、 methyl β-hydroxy-α-phenylvalerate
  参考文献：
  名称：

  Adam, Waldemar; Prechtl, Frank, Chemische Berichte, 1991, vol. 124, # 10, p. 2369 - 2372

  摘要：

  DOI：

文献信息

• The thionophosphate–thiolophosphate † photoisomerization proceeds predominantly through a non-chain radical pathway. Synthetically viable benzylation of tetrahydrofuran, propan-2-ol and olefins ‡
  作者：Veejendra K. Yadav、Rengarajan Balamurugan、Masood Parvez、Raghav Yamdagni

  DOI：10.1039/b003501g

  日期：——

  The photoirradiation of thionophosphates, ROP(S)(OEt)2, derived from benzyl and vinylogously benzyl alcohols in CH3CN, with a Hanovia medium-pressure mercury lamp in a quartz vessel leads to the formation of the corresponding thiolophosphates, RSP(O)(OEt)2, through a non-chain radical pathway. This behavior of thionophosphates is unlike that of the related phosphates, which react through ionic dissociation–recombination processes. When the irradiation is conducted in solvents such as PriOH, THF and toluene, benzylation of these solvents takes place in synthetically respectable yields. Irradiation of thionophosphates in CH3CN leads to a convenient allylic benzylation of olefins.

  从中式苯甲醇和苯乙烯式苯甲醇衍生得到的硫代磷酸酯ROP(S)(OEt)2，在CH3CN中使用Hanovia中压汞灯在石英容器中进行光照射，通过非链自由基途径形成相应的硫醇磷酸酯RSP(O)(OEt)2。硫代磷酸酯的这种行为与相关的磷酸酯不同，后者通过离子解离-重组过程进行反应。当在PriOH、THF和甲苯等溶剂中进行光照射时，这些溶剂会发生苯甲基化反应，产率可观。在CH3CN中对硫代磷酸酯进行光照射，可方便地使烯烃进行烯丙基苯甲基化。
• Unambiguous Proof for Alcoxycarbonyl-group Migration inWagner-Meerwein Rearrangements
  作者：Daniel Berner、Hans Dahn、Pierre Vogel

  DOI：10.1002/hlca.19800630849

  日期：1980.12.10

  HSO3F/SO2ClF the β-hydroxy esters Ph-CHOH-CMe2-COOR (1, RMe, Et) are doubly protonated, then transformed into the fluorosulfates 7 and (partly) into the fluorides 8. At −15°, both 7 and 8 undergo a rearrangement, forming derivatives of Me2CC(Ph)COOR (2). By labelling 1 with 13C, singly (13C(3)) and doubly (13C(1,3)), it could be shown that exclusively the ROOC groups undergo a 1,2-shift. Compound 2 is also

  在HSO 3 F / SO 2 ClF中，将β-羟基酯Ph-CHOH-CMe 2 -COOR（1，RMe，Et）进行双质子化，然后转化为氟代硫酸盐7和（部分）转化为氟化物8。在-15 °，7和8均发生重排，形成Me 2 CC（Ph）COOR（2）的导数。通过标记1与13 C，单独使用（13 C（3））和双（13 C（1,3）），则可以示出专门的ROOC基团经历1,2-移。化合物2也在HSO 3 F / SO中形成通过消除，从异构体Me 2 COH-CHPh-COOR（3）中除去2 ClF ，并且不容易通过苯基1,2-移位从α-羟基酯Ph-CMe 2 -CHOH-COOR （5）中除去2 ClF 。另一个异构体Ph-C（OH）Me-CHMe-COOR （4）得到的产品与2不同。
• Dimethyldioxirane Oxidation of Titanium Enolates: Diastereoselective .alpha.-Hydroxylations
  作者：Waldemar Adam、Michael Mueller、Frank Prechtl

  DOI：10.1021/jo00088a015

  日期：1994.5

  The oxidation of titanium enolates, derived from a transmetalation reaction of the corresponding lithium enolates with (i-PrO)(3)TiCl, (Et(2)N)(3)TiCl, or Cp(2)TiCl(2), by dimethyldioxirane has been investigated. Furthermore, the diastereoselective hydroxylation of the chiral metal enolates, e.g., derived from camphor (1f), menthone (1g), flavanone (1h), and 2-benzylcyclopentanone (1i), by dimethyldioxirane has been examined. The diastereoselectivity of the oxygen transfer strongly depends on the metal partner coordinated to the enolate. The titanium enolates 4 resulted in much higher diastereoselectivities (up to 96% de) than the corresponding sodium enolates 5 and at least as high if not higher than the silyl enol ethers 6. Moreover, the aldol reaction of ester-derived sodium enolates with acetone, the unavoidable medium for dimethyldioxirane, could be totally suppressed by the use of the chlorotitanocene enolates 4. Thus, the oxidation of chiral titanium enolates by dimethyldioxirane represents a general, convenient, effective, and chemo- and diastereoselective synthesis of alpha-hydroxy carbonyl compounds.
• Tomioka, Hideo; Okuno, Hiroshi; Izawa, Yasuji, Journal of the Chemical Society. Perkin transactions II, 1980, p. 1636 - 1641
  作者：Tomioka, Hideo、Okuno, Hiroshi、Izawa, Yasuji

  DOI：——

  日期：——
• Adam, Waldemar; Prechtl, Frank, Chemische Berichte, 1991, vol. 124, # 10, p. 2369 - 2372
  作者：Adam, Waldemar、Prechtl, Frank

  DOI：——

  日期：——