(R)-α-methylhydrocynnamic acid chloride | 38385-67-0

• 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: (R)-α-methylhydrocynnamic acid chloride
• 英文别名: (2R)-2-Methyl-3-phenylpropanoic acid chloride；D-2-methyl-3-phenyl-propionyl chloride；D-2-Methyl-3-phenyl-propionylchlorid；(2R)-2-methyl-3-phenylpropanoyl chloride
• CAS: 38385-67-0；81136-06-3；81136-08-5；81136-09-6
• 化学式: C₁₀H₁₁ClO
• 分子量: 182.65
• InChiKey: OWAWAFKVPTWIBP-MRVPVSSYSA-N

物化性质

• 沸点：
  123 °C(Press: 16 Torr)
• 密度：
  1.1 g/cm3(Temp: 23 °C)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (R)-α-methylhydrocynnamic acid chloride 在 三乙胺 、 碳酸二甲酯 作用下， 以 二氯甲烷 为溶剂， 反应 0.67h， 生成 methyl (2R)-2-methyl-3-phenylpropanoate
  参考文献：
  名称：

  A simple method removing 2-oxazolidinone and 2-hydroxyethylamine auxiliaries in methoxide–carbonate systems for synthesis of planar-chiral nicotinate

  摘要：

  A facile and practical removal of 2-oxazolidinone and 2-hydroxyethylamine auxiliaries was accomplished by treating the corresponding N-acyl-2-oxazolidin one and N-(2-hydroxyethyl)amide derivatives in simple methoxide-carbonate systems. The presence of excess DMC (dimethyl carbonate) accelerates the N-acyl bond cleavage for those substrates under mild reaction conditions, and the present method was found to be useful especially for the synthesis of planar-chiral nicotinate. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)00698-1
• 作为产物：
  描述：

  2-methyl-3-phenylpropionic acid 在 草酰氯 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 (R)-α-methylhydrocynnamic acid chloride
  参考文献：
  名称：

  Memory of chirality in rebound cyclizations of α-amide radicals

  摘要：

  (S)-N-(2-溴丙烯基)-N-(叔丁基)-2-甲基-3-苯基丙酰胺与三丁基锡氢化物还原后，得到(3S,4S)-3-苄基-1-(叔丁基)-3,4-二甲基吡咯烷-2-酮，其立体中心与酰胺羰基相邻处的手性保留率约为80%。这种手性记忆被认为是通过从一个立体中心转移到一个轴，然后再从轴转移到一个新的立体中心而发生的。

  DOI：

  10.1139/v2012-085

文献信息

• Diacyl Peroxide Reactions. III. The Behavior of the Optically Active 3-Phenyl-2-propyl Free Radical¹
  作者：DeLos F. DeTar、Claus Weis

  DOI：10.1021/ja01569a016

  日期：1957.6
• Intramolecular Nucleophilic Acyl Substitution Reactions Mediated by Samarium(II) Iodide: A Convergent Approach to the Preparation of Enantiomerically Enriched 4-Hydroxy Ketones from 3-Iodopropyl Carboxylates
  作者：Gary A. Molander、Sagar R. Shakya

  DOI：10.1021/jo00091a039

  日期：1994.6

  Intramolecular nucleophilic acylsubstitution (INAS) reactions of substituted 3-iodopropyl carboxylates have been achieved using samarium(II) iodide (SmI2) in the presence of an iron(III) catalyst. Diverse ester starting materials containing stereogenic centers placed in varying positions on the substrates have been converted to acyclic 4-hydroxy ketone derivatives in good yields using this method. No racemization of stereogenic centers alpha to the carbonyl was observed in any of the reactions examined. Consequently, the method serves as a convenient, high-yield synthesis of functionalized, enantiomerically enriched acyclic ketones possessing stereogenic centers far removed from one another.
• Potapov, V. M.; Dem'yanovich, V. M; Vendrova, O. E., Journal of Organic Chemistry USSR (English Translation), 1982, p. 1041 - 1043
  作者：Potapov, V. M.、Dem'yanovich, V. M、Vendrova, O. E.、Khlebnikov, V. A.

  DOI：——

  日期：——
• Potapov, V. M.; Dem'yanovich, V. M.; Vendrova, O. E., Doklady Chemistry, 1981, vol. 258, p. 221 - 223
  作者：Potapov, V. M.、Dem'yanovich, V. M.、Vendrova, O. E.、Khlebnikov, V. A.

  DOI：——

  日期：——
• HELMCHEN, G.;SELIM, A.;DORSCH, D.;TAUFER, I., TETRAHEDRON LETT., 1983, 24, N 31, 3213-3216
  作者：HELMCHEN, G.、SELIM, A.、DORSCH, D.、TAUFER, I.

  DOI：——

  日期：——