(R)-(1-phenyl)-1-propyl benzoate

• 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)-(1-phenyl)-1-propyl benzoate
• 英文别名: (R)-1-phenylpropan-1-yl benzoate；[(1R)-1-phenylpropyl] benzoate
• 化学式: C₁₆H₁₆O₂
• 分子量: 240.302
• InChiKey: XCHIHJDABCLLEG-OAHLLOKOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1-苯丙醇 、 (S)-3-benzoyl-4-tert-butyloxazolidin-2-one 在 甲基溴化镁 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 (R)-(1-phenyl)-1-propyl benzoate
  参考文献：
  名称：

  Studies directed toward the design of chiral acylating agents. The utility of chiral N-benzoylimides in enantioselective alcohol acylation

  摘要：

  N-benzoyl-4(S)-tert-butyl-2-oxazolidinone (1b) is found to be an efficient enantioselective acylating agent for aryl n-alkyl carbinols. Selective benzoylation of racemic aryl n-alkyl carbinols with kinetic selectivities of 20-30:1 for the (R) enantiomer is observed. The acylation process is promoted by formation of the derived magnesium alkoxides which may be accessed either from alcohol deprotonation with MeMgBr or through deprotonation with the Lewis acid-base combination of MgBr2/R3N.

  DOI：

  10.1016/s0040-4039(00)73882-2

文献信息

• SuperQuat 5,5-dimethyl-4-iso-propyloxazolidin-2-one as a mimic of Evans 4-tert-butyloxazolidin-2-one
  作者：Steven D. Bull、Stephen G. Davies、A. Christopher Garner、Dennis Kruchinin、Min-Suk Key、Paul M. Roberts、Edward D. Savory、Andrew D. Smith、James E. Thomson

  DOI：10.1039/b605244d

  日期：——

  The incorporation of a gem-dimethyl group at the 5-position of a chiral oxazolidinone biases the conformation of the adjacent C(4)-stereodirecting group such that the gem-dimethyl-4-iso-propyl combination mimics a C(4)-tert-butyl group, providing higher levels of stereocontrol than a simple 4-iso-propyloxazolidinone. The generality of this principle is demonstrated with applications in stereoselective enolate alkylations, kinetic resolutions, Diels–Alder cycloadditions and Pd-catalysed asymmetric acetalisation reactions.

  在手性噁唑啉酮的5位引入一个双甲基基团会使得邻近的C(4)立体导向基团倾向于特定构象，即双甲基-4-异丙基的组合能模拟一个C(4)叔丁基基团，从而实现更高的立体控制水平，优于简单的4-异丙基噁唑啉酮。这一原理的普遍性在立体选择性烯醇化物烷基化、动力学拆分、狄尔斯-阿尔德环加成和钯催化的不对称缩醛化反应中得到了应用验证。
• Microscale Determination of the Absolute Configuration of α-Aryl-Substituted Alcohols by the CD Exciton Chirality Method
  作者：Waldemar Adam、Zoltan Lukacs、Kirsten Viebach、Hans-Ulrich Humpf、Chantu R. Saha-Möller、Peter Schreier

  DOI：10.1021/jo991424i

  日期：2000.1.1

  The absolute configurations of a broad spectrum of aryl alcohols 1 have been determined for the first time by the CD exciton chirality method. The configurational assignment is additionally verified by computer modeling and lipase-catalyzed acetylation of the racemic alcohols. The CD-spectroscopic data have revealed that the S enantiomers of the benzoate derivatives 2 display a positive first Cotton

  宽范围的芳基醇1的绝对构型已通过CD激子手性法首次确定。通过计算机建模和外消旋醇的脂肪酶催化的乙酰化进一步验证了构型分配。CD光谱数据表明，苯甲酸酯衍生物2的S对映异构体在约228nm处显示正的第一棉花效应，而R对映异构体显示负的棉花效应。因此，对苯甲酸酯衍生物2的第一棉效应的感觉允许可靠分配相应的醇1的绝对构型。
• Kinetic resolution of sterically hindered secondary alcohols catalyzed by aminophosphinite organocatalyst
  作者：Nanami Hara、Shu Fujisawa、Mizuki Fujita、Mikako Miyazawa、Kazuma Ochiai、Satoshi Katsuda、Tetsuya Fujimoto

  DOI：10.1016/j.tet.2017.11.062

  日期：2018.1

  Kinetic resolution of secondary alcohols by benzoylation using a phosphinite derivative of (1S,2R)-1-amino-2-indanol as the catalyst was investigated. The aminophosphinite catalyst is effective for the kinetic resolution of aryl cycloalkyl carbinols with a small number of examples for organocatalytic kinetic resolution to achieve resolution with s = up to 44. Although the benzoylation of phenylalkanols

  以（1 S，2 R）-1-氨基-2-茚满醇的次膦酸酯衍生物为催化剂，通过苯甲酰化反应，研究了仲醇的动力学拆分。氨基次膦酸酯催化剂对芳基环烷基甲醇的动力学拆分有效，其中有机催化动力学拆分的实例较少，以达到s  =高达44的拆分。尽管苯基链烷醇的苯甲酰化反应选择性低，但至少带有1-芳基链烷醇苯环上邻位的一个取代基或甲醇碳上的支链烷基以可接受的选择性被拆分。
• Studies directed toward the design of chiral acylating agents. The utility of chiral N-benzoylimides in enantioselective alcohol acylation
  作者：David A. Evans、James C. Anderson、Marta K. Taylor

  DOI：10.1016/s0040-4039(00)73882-2

  日期：1993.8

  N-benzoyl-4(S)-tert-butyl-2-oxazolidinone (1b) is found to be an efficient enantioselective acylating agent for aryl n-alkyl carbinols. Selective benzoylation of racemic aryl n-alkyl carbinols with kinetic selectivities of 20-30:1 for the (R) enantiomer is observed. The acylation process is promoted by formation of the derived magnesium alkoxides which may be accessed either from alcohol deprotonation with MeMgBr or through deprotonation with the Lewis acid-base combination of MgBr2/R3N.