1-acetoxy-2-methylpropyl phenyl ketone | 104426-40-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-acetoxy-2-methylpropyl phenyl ketone
• 英文别名: 3-methyl-1-oxo-1-phenylbutan-2-yl acetate；1-Butanone, 2-(acetyloxy)-3-methyl-1-phenyl-；(3-methyl-1-oxo-1-phenylbutan-2-yl) acetate
• CAS: 104426-40-6
• 化学式: C₁₃H₁₆O₃
• 分子量: 220.268
• InChiKey: AILSDVUYGNJLEI-UHFFFAOYSA-N

物化性质

• 沸点：
  306.9±15.0 °C(Predicted)
• 密度：
  1.060±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-acetoxy-2-methylpropyl phenyl ketone 生成 R-(-)-1-phenyl-2-hydroxy-3-methylbutanone
  参考文献：
  名称：

  OHTA, HIROMICHI;IKEMOTO, MITSUSHI;II, HIROYUKI;OKAMOTO, YASUSHI;TSUCHIHAS+, CHEM. LETT., 1986, N 7, 1169-1172

  摘要：

  DOI：
• 作为产物：
  描述：

  3-甲基-1-苯基-丁-1-炔 在 水 作用下， 以 二氯甲烷 为溶剂， 反应 12.67h， 生成 1-acetoxy-2-methylpropyl phenyl ketone
  参考文献：
  名称：

  硫介导的内部和末端炔烃双官能团合成α-乙酰氧基酮

  摘要：

  据报道，炔烃的硫介导的双官能团化可以在温和的条件下，通过一锅操作以19-92％的收率得到α-乙酰氧基酮。通过使用湿乙酸钾作为碱水溶液和亲核试剂，末端炔烃和内部炔烃都可以转化为α-乙酰氧基酮产物。

  DOI：

  10.1016/j.tetlet.2020.151707

文献信息

• Preparation of Optically Active α-Acetoxyacylophenones via Enzyme Mediated Hydrolysis
  作者：Hiromichi Ohta、Mitsushi Ikemoto、Hiroyuki II、Yasushi Okamoto、Gen-ichi Tsuchihashi

  DOI：10.1246/cl.1986.1169

  日期：1986.7.5

  Microorganisms that hydrolyzes α-acetoxyacylophenones were screened, and it was found that Pichia miso IAM 4682, a type culture belonging to yeast, gave the best results. The esterase of this microbe hydrolyzed (R)-acetates in a highly enantioselective manner.

  筛选了水解α-乙酰氧基苯甲酮的微生物，发现属于酵母的典型培养物毕赤酵母IAM 4682给出了最好的结果。这种微生物的酯酶以高度对映选择性的方式水解 (R)-乙酸酯。
• Preparation and reactivity of highly functionalized organometallics at the .alpha. position of oxygen or nitrogen
  作者：Paul Knochel、Tso Sheng Chou、Carole Jubert、Duddu Rajagopal

  DOI：10.1021/jo00055a010

  日期：1993.1

  Alpha-Halogenoalkyl carboxylates (FG-R1CH(X)(OCOR2); FG = COOR, CN, SR; X = I, Br) were readily prepared by the addition of an acid chloride or bromide (R2COX; X = Br or Cl) to an aldehyde (FG-RCHO) in the presence of a catalytic amount of ZnCl2. They insert efficiently zinc dust in THF-DMSO (X = Br, 8-10-degrees-C, 6-10 h) affording the corresponding zinc organometallics at the a position to oxygen FG-RCH(ZnBr)(OAc). After the addition of the THF-soluble copper salt CuCN.2LiCl, the corresponding copper reagents FG-RCH(Cu(CN)ZnBr)(OAc) are formed and reacted with various classes of electrophiles such as acid chlorides, aldehydes, enones, allylic and alkynyl halides, activated alkynes, nitro olefins and alkylidenemalonates providing polyfunctional molecules in excellent yields. Similarly, zinc organometallics at the a position to the nitrogen of cyclic imides were prepared by the zinc insertion to cyclic alpha-chloromethyl (or alpha-chloroethyl) imides. After their transmetalation to the corresponding copper organometallic ((R1CO)2NCH(R)(Cu(CN)ZnCl); R = Me or H), they were reacted with allylic and alkynyl halides and ethyl propiolate affording polyfunctional imides. The reaction of cyclic N-(chloromethyl)imides with aldehydes in the presence of chromium(II) chloride in THF furnishes protected amino alcohols in 36-95% yield.
• Ohtsuka, Yasuo; Oishi, Takeshi, Chemical and pharmaceutical bulletin, 1983, vol. 31, # 2, p. 443 - 453
  作者：Ohtsuka, Yasuo、Oishi, Takeshi

  DOI：——

  日期：——
• A general preparation of highly functionalized zinc and copper organometallics at the .alpha.-position to an oxygen
  作者：Tso Sheng Chou、Paul Knochel

  DOI：10.1021/jo00303a007

  日期：1990.8
• CHOU, TSO-SHENG;KNOCHEL, PAUL, J. ORG. CHEM., 55,(1990) N6, C. 4791-4793
  作者：CHOU, TSO-SHENG、KNOCHEL, PAUL

  DOI：——

  日期：——